The 47 Most Amazing Airbnbs for Families Across the Country
We know your travel plans may have changed due to the COVID-19 outbreak; we also know this won’t last forever. So whether you’re looking for a safe staycation or nearby getaway for this summer, or you are planning that big reunion for next year, we’ve pulled our favorite Airbnb rentals for families from across the country. These family-friendly vacation rentals offer great locations, unique stays and more, all at prices much lower than hotels. Please note, prices listed were valid at the time of publication but rates can fluctuate at different times of the year. Scroll on to see our top picks.
Hood Canal Cabin—Hoopdsport, WA
This Airbnb rental on the Hood Canal has everything a PNW vacation home should. Kayaks and rowboats (with lifejackets too!) are available for use on the over 100 feet of private waterfront just outside the home. Spend your days digging for clams and oysters nearby; then bring them back to grill on the deck while you watch the sun set. Bring fixings for s’mores and head down to the fire pit to enjoy those with the kids once dinner’s over. The house is close to the Olympic National Park entrance (remember your park pass) and Lake Cushman activities, too. Weekend or week … you’ll find plenty to do.
Sleeps: 5 guests
Robert’s Bluff Bungalow—Whidbey Island, WA
Your beach side bungalow awaits at this island home just a short ferry ride away. Spend the day playing peek-a-boo with Mt. Rainier and Mt. Baker, throwing crab pots off the pier or giving the kids extra time on the playground. Families can also fish just down the beach and should definitely check out the free little library that’s close by to find a good read. The bungalow is cozy and has a modern farmhouse feel. The fireplace makes it a great rental to consider as we move from summer into the cooler nights of fall.
Sleeps: 4 guests
Barn at Raspberry Ridge Farm—Poulsbo, WA
If green acres is the life you need, book the barn apartment at Raspberry Ridge Farm. Located on a 17-acre working farm, the kids will find plenty of room to run and probably make a few barnyard friends while they’re at it. Families will also find over 60 miles of hiking trails just next to the property, so bring your sunscreen and hiking poles if socially-distanced exploring is on your list. The barn includes a full kitchen so you can cook instead of head to town, WiFi, TV and a deck with mountain views. Upscale Old McDonald is how this farm rolls.
Good to know: Families can also add Bainbridge Island to their spots to explore.
Sleeps: 4 guests
Home Away—Gig Harbor, WA
Bring board games and some good books because you’ve got this Gig Harbor house to yourself. It’s got everything a family needs to get away from the city, including a killer view of the harbor. The house is within walking distance to the Gig Harbor waterfront, where you’ll find welcoming restaurants and shops, and you may even spot a few harbor seals while you’re there. Bring the kayaks and SUPs to Eddon Boat Park, a sheltered spot that makes kayaking with kids easy, or make like a local and bring them to Bella Bella beach on Fox Island for a change.
Sleeps: 6 guests
EDITOR'S PICK: Architectural Retreat—Seattle, WA
If you’ve got a little LEGO lover in the fam, he or she is going to think everything about this house is awesome! The bright and funky architectural home (Wendell Lovett) includes LEGO design elements in the kitchen and LEGO wall art (using real bricks!), as well as plenty of open space and light-filled rooms. Parents and kiddos alike will love the A-frame design and spots of bright colors and stylish furnishings around every corner.
Set back on a wooded lot (with an outdoor eating space), the home features three bedrooms, a loft and two and a half bathrooms and feels very open and airy with its high vaulted ceiling and open stairwell. This house has easy access to Matthews Beach and Magnuson Park (two kid faves), as well as the retail shops and restaurants at University Village. It is just far enough away from downtown Seattle to feel private, but also close enough when it’s time to go have fun.
Cost: $260 per night
Wine Country TreeHouse & Herbal Farm—Newberg, OR
Just 40 minutes from Portland, this treehouse escape was built by the master tree builder Pete Nelson of Animal Planet's TreeHouse Master. Get ready to enjoy stunning hillside views and access to over 300 area wineries. Eat in with the onsite kitchen available for making home-cooked meals, or head to the nearby town of Dear Haven (just 30 miles away) for a meal and to peruse local shops. Breakfast is provided, so you can take every morning as slow as you like.
And while this is an ideal destination for adults, there's plenty to keep the kids entertained.
For the Kids
Located on a small farm with no televisions on-site to take away from the charm, there's lots of room for youngsters to explore. This site offers a truly unplugged experience for families looking to bond in nature. Note: This location is not appropriate for children 2 and under.
EDITOR'S PICK: The Hobbit Hole—Portland, OR
Surprisingly affordable, this is one of the best Airbnb’s vacation rentals we've seen. Cozy up in this work of art that's designed to make you (and the kids–it’s about the kids, right?) feel like you're part of the Hobbit's epic adventures. From the furniture to the walls and ceilings this handcrafted, sustainable abode is inspired by the Lord of the Rings and is guaranteed to infuse your vacation with magic. It's made from reclaimed clay, tree roots and reclaimed materials, which you'll discover throughout the entire space. There's also a Hobbit-friendly memory foam queen bed, a leather sofa sleeper (also with memory foam), a kitchenette with nearby dining area decked out with Swarovski crystal chandelier and a European-styled bathroom.
Staying in a Hobbit house will thrill any child, but it's extra neat that the owners included a high chair, Pack 'n' Play, children's toys and books, outlet covers and children's dinnerware. There's also a beautiful little yard for youngsters to enjoy.
Sleeps: 4 guests
Cost: $125 per night
Beautiful, Magical Treehouse—Mt. Hood, OR
For a real mountain experience, rent this luxury treehouse for just $150 a night. This magical abode is suspended between three large fir trees on 20 acres of property at the base of Mt. Hood. It boasts four beds, so everyone has enough space and comes with a composting toilet, mini-fridge, and microwave for a true glamping experience. There is a swirling, spiral staircase that inspires wonder as you ascend to your family suite, where you will find about 200 square feet of space with a sleeping loft. The kids won't want to leave once they are settled in. And with a beautiful seating area below the treehouse, mom and dad might not want to either.
For the Kids
There is a one-acre pond with kayaks and a nearby zipline for plenty of adventure perfect for busy little (and big) bodies. For the quieter set, there is a beautiful garden and a rowboat to float around in. Onsite hiking, disc golf, horseshoes, basketball and a pendulum swing ensure everyone has something to do.
Grand and Cozy 1920s Studio—San Francisco, CA
Head back in time when you step into this classy 1920s studio located in San Francisco at Powhattan Avenue and Prentiss Street in what was once a historic corner store. Now tastefully remodeled, guests can get a taste of life in the city while residing in the comforts of a home. Families can find a kitchenette, fireplace, curtained sleeping and living spaces, WiFi, cable, a dining area and more. The studio accommodates four people, has two beds and one bath.
What to do: Take in the sweeping views of The City by the Bay when you walk two blocks down the street to Bernal Park.
Train Caboose in the Redwoods—Cupertino, CA
How cool is this? You can stay in your very own train caboose in the South Bay that comes with three beds and a kitchen. There are lots of nearby hiking and biking trails, as well as other exciting outdoor activities. Being so close to Silicon Valley, yet feeling so far from it all is a truly unique experience unlike anywhere else.
What to do: Check off all the South Bay destinations on this roadside oddities list, like the Facebook thumbs up sign.
Yosemite Mountain Home—Oakhurst, CA
Get away from it all with a stay at this lovely mountain home near Yosemite. Only 30 minutes from the south gate of Yosemite, it's the perfect home base for your national park visit. Head to downtown Oakhurst to stock up on snacks and then spend the day in the park or at vBass Lake (only a 12-minute drive). You'll have two kayaks available to use during your stay. Winter visitors can take advantage of the home's proximity to Badger Pass Ski Area.
What to do: Visit the Giant Sequoias at Yosemite, they are amazing to see!
The Pearl of Muir Beach—Muir Beach, CA
Make sure to snag your reservation for this private and roomy home near Muir Beach, another visitor destination along California’s regal coast. Two queen beds and a pull-out sofa are available in this two-bedroom house just steps from the beach, and guests can also find great hiking trails. Those traveling with kids will love the pack n' play, toys and highchair that are on-site (request a toddler bed if you need it). The owners provide a surfboard, boogie board and two bikes for you to use during your stay.
Things to do: This area is well known as a gorgeous kayaking destination. Get your life jackets on and get ready to explore!
Deltahouse Waterfront Getaway—Discovery Bay, CA
Wake up to the calm Delta waves when you stay at this waterfront home in Discovery Bay, the community with a "Live Where You Play" slogan. At this end of Contra Costa County, the people still live the slower-paced lives of more genial times beside rows of crops and open land while remaining in reach of San Francisco and other globally known cities. This spot is a great getaway when grandparents are in town as it has enough room for everyone to spread out with three bedrooms and three bathrooms. Floats and rafts for swimming (as well as life jackets) are available. Kids looking for some play time on-land can dig around in the sandbox.
What to do: Rent a stand-up paddleboard, kayak or jet ski or sail away on a guided cruise tour of the Delta on Captain Morgans Delta Adventures while watching the sun set. In this family-centric community, mostly everything is kid-friendly.
EDITOR'S PICK: Redwood Treehouse—Watsonville, CA
Give your family the experience of a lifetime once you climb into the boughs of this unique destination. Located in Watsonville just south of Santa Cruz, the redwoods surround the treehouse Airbnb, which is fully equipped with a kitchen, bed and bath and only 25 minutes from the ocean. Visitors can enjoy a scenic walk along a dirt path before reaching the treehouse. Soak in the nearby hot tub while also soaking up a relaxing, rejuvenating experience surrounded by nature’s bounty. Bonus for cat lovers as the treehouse comes with “Grey” a friendly outdoor feline!
Sleeps: 2 Guests (great for an intimate getaway with one older kid)
Cost: $158 per night
Hollywood Hideaway—Los Angeles, CA
With soaring ceilings, arched doorways and charming built-ins, this 2-bed, 2-bath 1930s home will transport you to Old Hollywood. The stunning tiled blue pool will be a hit with both kids and adults. Plus, unlike many rentals currently available, this location doesn't have a minimum stay, which means you can get away for just a night or two.
EDITOR'S PICK: Castle with a Pool—Los Angeles, CA
For your little knights and princesses, this newly restored 1920s castle is straight out of a storybook. Original details like stone turrets, gothic arches and exposed beams abound. It's a splurge, but so worth it. The grounds are completely enclosed by stone walls and offer a private courtyard off the master, a built-in fire pit and a spacious pool to play in.
Mountain Retreat—Topanga, CA
Tucked away in the hills of Topanga, this clean and character-filled 3-bedroom home offers mountain views, multiple patios and a backyard wooded path to explore. The third bedroom has two built-in platform twin beds perfect for kiddos who will feel like they're sleeping in their own little treehouse.
Mandalay Mid-Century—Oxnard, CA
Also in Oxnard, just above Hollywood Beach, there's the secluded Mandalay Beach where this family beach house is situated. It offers 3 bedrooms and 2 baths and plenty of mid-century style. This space is super kid-friendly, with a crib and twin bed in one room, plus an adorable play house on the back patio.
Cardiff Sea Cottage—Cardiff by the Sea, CA
This beautiful beach cottage screams San Diego summer. Located just a five-minute walk to the park & San Elijo Lagoon, and less than one mile to iconic Cardiff and Encinitas beaches, the location can't be beaten. Catch the sunset on the expansive covered patio deck and enjoy the sea breeze while toasting the day with your favorite drink. You can also walk from the cottage to a handful of restaurants and the world-famous Seaside Market. Additionally, enjoy a local hike through Cardiff located just five minutes from this house and soak up the beauty of San Elijo Lagoon. The hosts even provide beach chairs, beach towels, umbrella and boogie board.
Bonus: Children's books and toys and a Delta Children portable mini crib with a thick mattress.
The Charming Castle—San Diego, CA
If your little princes and princesses have always dreamed of staying in a castle, this South Park rental will make those wishes come true. The curb appeal will enchant your whole family: a turreted roof, lopsided windows and manicured trees set the stage for fairytales. Inside, you'll find all the usual amenities, including a pack 'n' play for your littlest guests.
What to do: As if the castle itself weren't enough, this home is located steps away from parks and trails. South Park provides plenty of walkability with shops and restaurants nearby. The San Diego Zoo and Balboa Park are a quick drive away.
The Tremendous Treehouse—Julian, CA
If you're looking for something rustic, this property in Julian is not your average cabin in the woods. Spend your days wandering trails on your private acre of forest land or gazing up at the starry sky at night. Historic Julian and Cuyamaca Lake are both close by, where your family can enjoy picnics, fishing, and of course, pie.
What you'll love: Oh, did we mention the treehouse? This cottage cabin connects to a floating bridge that brings you to a treehouse high in the pine trees, ensuring giggles and gasps of wonder from kids and adults alike. There's also a spa and home theater.
EDITOR'S PICK: The Joshua Tree House—Joshua Tree, CA
Dreaming of starry desert skies and solace among the wild cacti? If you want to immerse yourself in the majestic surroundings of Joshua trees, The Joshua Tree House is a gorgeously decorated home where your family can enjoy a slow-paced vacation in this serene spot. You'll love the exquisitely decorated interior of this 2 bed/2 bath hacienda built in 1949. It's perfectly appointed 10 minutes from the west entrance of Joshua Tree National Park and just about a 10-minute walk from downtown Joshua Tree, where you'll find several shops and restaurants. The swinging chairs in the living room will certainly be your kids' favorite place to perch.
The Earthship—El Prado, NM
The Phoenix Earthship (which is located near Taos, NM, not Phoenix, AZ) is a work of art and guaranteed to make a unique family vacation the kids will never forget. The greenhouse makes a lush environment in the high mountain desert, with banana trees, grapevines, birds, turtles and a fish pond. The entire property is off grid, sustainable and unique. There is also a food garden, chickens and views of the Sangre de Cristo Mountains. Part of a massive 630-acre Earthship subdivision, the only official off-grid subdivision in the world, you'll find stars for days. It's also driving distance to artsy Taos.
Tiny House Near Magnolia Market—Waco, TX
If you've been wanting to take a trip to check out Magnolia Market and perhaps catch a glimpse of your favorite Fixer Upper stars, Chip and Joanna Gaines, The Helm is the coziest spot around. This tiny house accommodates up to 4 guests and boasts lots of high-end amenities. And of course, shiplap.
The Silo House at Laughing Llama Farm—Troy, TX
Located near Waco, Texas and about 20 miles from the downtown area, this expansive farm stay includes an incredibly unique converted grain silo with all the amenities, including a sleeping loft, full bathroom, kitchen and a fishing pond on site. Visit with the sheep and llamas and relax in the peace and quiet.
Rural Escape—Gilbert, AZ
Got a big group? The main home is a 3200 sqft Ranch Style 6BD/6BA set up to sleep 12 guests! An expansive patio, heated pool, hot tub, bunnies, chickens and an acre of grass to play makes it a great gathering spot for small family groups. It's also located in a neighborhood known for horse properties (so you're likely to see horses gallop by) and is just 20 minutes from the airport.
Folk Tree Farm—Washington Island, WI
Located in scenic Door County, WI, on Washington Island, this entire farm stay is perfect for any family who truly wants to get away from it all. The upstairs of the farmhouse is your home away from home on this 21-acre farm where your kiddos can meet chickens, goats, cows and more. Friendly dogs are welcome too, with plenty of space to run.
Sleeps: 7 (3 bedrooms, 5 beds)
Amish Country Farmhouse for a Group—Apple Creek, OH
This modern four-bedroom Dawdi Haus (Amish grandparents home) is located right in the heart of Amish Country. Explore the beautiful two-acre property with a barn for your animals. Start up the grill and spend the evening near the fire pit. The kids will like the air hockey and foosball tables, and the game closet has a little something for everyone.
Retreat Near Cuyahoga Valley National Park—Hudson, OH
Enjoy your time at this lovely home that's only eight miles from Cuyahoga Valley National Park. The house is located on a nice, quiet street with easy access to grocery stores and shopping. Enjoy your evenings in the backyard after a day spent hiking nearby.
EDITOR's PIC: Lakefront Retreat on Portage Lakes—New Franklin, OH
This beautiful and spacious waterfront four-bedroom home is perfect for all your getaway needs! Bring your boat and dock at the property, or rent one near by. There are many great local restaurants accessible by boat. Enjoy the firepit and fish from the dock. There's a game closet full of indoor fun if you catch bad weather.
Sidelined Pullman Train Car—Plano, IL
Oh, the stories this Pullman Train car, the Constitution, could tell. Built in 1905, it was basically Air Force One for Presidents Harding and Wilson, and when the president of the Illinois Railway Museum visited, he said it was the most well-preserved Pullman train car in the U.S. A large living room with fireplaces, a master bedroom and bathroom have been added to the original car, which consisted of four staterooms, an observation deck, a dining room and a galley. This is all set atop a bluff overlooking Big Rock Creek and a floodplain full of 200-year old oak trees where you might see an Eagle or two. During the summer months, there's even a pool onsite to enjoy.
We recommend bringing along a few groceries to utilize the kitchen facilities and make this a true staycation. Unplug and fully immerse yourself in a getaway with a country feel.
Sleeps: 6 guests; 3 bedrooms, 3 beds, 3 baths
Northern Retreat—Nisswa, MN
Perfect for a family reunion, the Northern Retreat sits on the edge of Roy Lake and contains three buildings over five acres. Here you’ll find eight bedrooms with 11 beds, nine bathrooms, a private tennis court, two exercise rooms, two screen-in porches, three decks, a barrel sauna, hot tub, a game room (that features a pool table, ping pong, foosball and a popcorn machine) and a most impressive movie theater room with nine reclining and a big-screen movie wall.
Outside you’ll find a walking trail, two fire pits and 32-foot long dock. The house is located just a mile from the town of Nisswa that has several fun shops, restaurants and activities and the Paul Bunyon Trail.
Cost: $1135 per night
Converted Church in Logan Square—Chicago, IL
While this spot teeming with history is a bit of a splurge, it can accommodate a larger group looking to split the tab. Construction on this former church began in 1888, and it functioned in a religious capacity until private owners began the conversion in 1990. Since then, it's been featured in Chicago Tribune Home Design Magazine, on the first season of HGTV's Extreme Homes and is regularly tapped for not-for-profit house tours, including the Art Institute, the Museum of Contemporary Art, the Lyric Opera Guild and more.
Logan Square is home to the only weekly, year-round farmers market in Chicago, held indoors during winter months and outdoors in the summer. It's a low-key spot to grab an inexpensive breakfast or lunch or stock up on fresh ingredients for a meal prepared back at your home-away-from-home. If you want a break from cooking, Revolution Brewery is just down the way and is great for grub and a cold beer. Be sure to try their parmesan bacon popcorn! A fun resource nearby is Four Star Family Cyclery, which rents swoon-worthy cargo bikes you'll want to take home.
Editors Pick: Chicago Treehouse—Chicago, IL
Glamp the night away in this cedar treehouse which is outfitted with a fireplace, air conditioning, private deck, kitchenette (with sink, microwave, fridge and coffeemaker), Wi-Fi and hi-def cable TV with premium channels. The treehouse comes with a full-size bed and a twin sleeping loft with feather bed comforters. Bathroom accommodations (somewhat less glamorous, but remember, you’re glamping) include a private RV-type toilet and covered outdoor shower with lots of hot water.
Down below (you can climb down the ladder or take the fireman’s pole shortcut), you’ll find the hot tub situated nearby a waterfall and koi pond. Dine al fresco in the beautiful garden cooking on the gas grill and enjoy your meal on the fire table.
There's no shortage of family activities in Schaumburg, but consider a trip to LEGOLAND Discovery Center, which has two rides, 10 LEGO build and play zones, a 4D cinema, impressive LEGO structures to gawk at and more. It sounds like a journal-worthy birthday weekend for a special little one!
Sleeps: Up to 3 guests
Cost: $235 per night
Secluded Intown Treehouse—Atlanta, GA
This property is Airbnb's #1 most wish-listed property in the world and is described as being the most relaxing, romantic, dreamy and unique place you'll ever stay. So this one is probably more of a date night getaway or maybe a special occasion overnight with an older kiddo. What could be better than falling asleep in the trees and waking up to birds singing around you—all within the city limits? Located near Northside Drive in Buckhead, visitors here will have easy access to the interstate, Buckhead and Midtown.
Buckhead Carriage House—Atlanta, GA
If Southern charm is what you're after, then this graceful Buckhead Carriage House is for you. Situated in the heart of Atlanta's in-town neighborhood known for its restaurants, shopping, and beautiful homes (also for the Legoland Discovery Center, Atlanta History Museum, and within striking distance to some of the city's prettiest parks and playgrounds), this beautiful abode with its own pool is perfect for families.
EDITOR'S PICK: Llama Luxury Cottage
Just a few minutes away from downtown Atlanta you’ll find this luxury cottage “guarded” by alpacas and the beautiful Dali Llama. Image waking up in a super comfy memory foam bed to real roosters instead of an alarm clock. Then, make breakfast with farm-fresh eggs in a beautiful granite kitchen. Afterward, you can feed the llamas, play a board game or two or travel into town. Enjoy the garden from the cottage patio. The home is equipped with children’s toys, TVs and Wi-Fi too. The place is a mixture of casual comfort and elegant touches. Get a sense of what it’s like to live on a farm without having to leave the city.
Cost: $120 per night
The Disney House—Davenport, FL
Located just one exit away from Disney World, your kids won’t complain when it’s time to go back and rest. There’s the 101 Dalmatians room with spotted walls, twin beds and stuffed dogs everywhere. The Frozen room is decked out with floor to ceiling decorations from the movie and stuffed Olaf and friends on the twin beds. Mom and Dad will appreciate the Mary Poppins master suite. The house’s game room is themed with Star Wars and features a space-age ping pong table, a conventional pool table and foosball table game. In case the kids didn’t burn off enough energy at the theme parks, there will be pretty of time to do so in the home’s private indoor pool.
The home also comes with a full kitchen, dining room that seats 10, living room, air conditioning and TVs in every bedroom. A grocery store and fast food options are only a mile away too.
Cost: $135 per night
The Luxe Loft—Nashville, TN
This unique boutique loft sits closes to everything (you can walk to Music Row) but is also tucked away for privacy. The two-bedroom home features a full kitchen with Italian appliances, a private deck, memory foam mattresses and designer bedding, over-sized spa shower, designer fixtures, hickory floor, vintage Persian rugs and HDTVs. This place is loved by families and comes highly recommended as it is equipped with a travel crib, books and toys and more.
Cost: $114 per night
A Backyard Paradise—Annapolis, MD
This property has been nicknamed the Petit Resort because you will feel like you're tucked into your own private retreat. But petit it is anything but. This house can accommodate up to 10 guests in six bedrooms. Relax on-site in the hot tub or the pool or take a short walk (or water taxi) to downtown Annapolis for fresh seafood and waterside dining. Bonus: these super hosts employ the latest technologies and cleaning products to make sure this rental is clean as a whistle (and based on reviews, they're doing a great job).
Getting Cozy by the Cottage—Chesapeake, VA
This private cottage offers waterview rooms from nearly every be in the house; there are 3 bedrooms to accommodate up to 6 guests (including a set of bunk beds for the littles). Get direct access to the Chesapeake Bay from this property or take a dip in the home's pool or hot tub. Amenities at this cottage include two kayaks, a stand up paddleboard, a crab pot and dip net, a charcoal grill, a fire pit and two adult bikes.
The Kiddie Pool—Arlington, VA
This large home in the heart of Clarendon in North Arlington offers a wading pool perfect for pint-sized swimmers. Before or after your dip, don't forget to roast marshmallows in the outdoor fire pit. Feel free to leave your car at home; this house is conveniently located near a metro stop.
EDITOR's PICK: Classic Scandinavian Kid Haven—Washington, DC
This 100+-year-old historic row house located in D.C.'s Mt. Pleasant neighborhood is perfectly situated to fun spots for the entire family, including Rock Creek Park and the National Zoo that are next-door neighbors, and the White House and National Mall that are two miles away. After exploring the city, let the kids hang in the playroom with toys, books, Wii games or splash in the ball pit (yes! there's a ball pit!).
From a guest: "The attic room is a kid's haven. We had to drag them out every day. They enjoyed the ball pit, puppets, LEGO, drum set, Wii game console, and a myriad of other toys."
A Berkshire Cottage at a Discount—Monterey, MA
The kind-hearted proprietors of this cozy cottage near Great Barrington, Mass, have discounted the rate for weekly and monthly rentals to help people find some respite from the city. In addition to being near area attractions like a nearby beach and hiking, this place looks primo for enjoying fall foliage, and it even has a gazebo for taking in nature's splendor.
EDITOR'S PICK: A Woodland Fairy Escape—Tyringham, MA
The scene at The Santarella Estate and Gardens is nothing short of magical, with its gorgeous grounds featuring garden paths, a babbling brook, stone bridges, a lily pond, and two acres of woods with a loop trail. (Very Hobbit/fairy-friendly here.) And then there’s there Grand Silo Tower on the property, which looks sprung from Tolkien’s imagination or Myst. These unique accommodations feature a spiral staircase up to a canopy queen bed, a kitchenette and large bath, and a connected studio space with a sitting area, wood pellet stove and a ping-pong table (The couch converts to a full-size bed for two additional guests, for which there is an additional charge.). Santarella is located near the area attractions and towns such as Tanglewood, Great Barrington, the Norman Rockwell Museum, Lenox and more. There’s also a local swimming hole nearby! (Note: if this spot is booked, there are other properties on-site.)
Cost: $257/night + additional guest fee
A Cozy Bargain in the Poconos—Saylorsburg, PA
It's cute and compact, and the price is right! This little cottage in the Poconos is small but mighty, with peaceful sitting areas, a fire pit, grill, patio string lights, and it's also pet-friendly. Plus, it's near hiking, flea markets and other area attractions.
The Ranch With Outdoor Luxuries—Kerhonskon, NY
A hot tub, tank pool, outdoor movie screen and fire pit nestled in the wilderness? Yes, please! (And that's just on the outside!) Stony Hill Ranch has four bedrooms and three-and-a-half baths, as well as a "Jam Shed" where you can rock out for an additional deposit. The property is in Kerhonkson, NY near the Shawangunk Mountains, but it's also near a Wal-Mart if you need to stock up on things.
—Jeffrey Totey with Red Tricycle Editors