Family-friendly vacation rentals in Whitingham

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Whitingham family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
An outdoor deck features a round table surrounded by four black metal chairs, offering a panoramic view of rolling hills and trees. The clear blue sky complements the lush greenery of the landscape.
Apartment in Townshend
4.93 out of 5 average rating, 240 reviews

Private Apt. on Farm, Hot Tub with views!

MathildeRating, 5 stars3 weeks ago
Amazing view, great and comfy Airbnb. The hot tub is such a nice plus with the incredible view over the mountains. It was so well equipped we had most of our meals in the Airbnb because the kitchen was so functional. I highly recommend this Airbnb!
Top guest favorite
A bright living area features a comfortable seating arrangement and large windows that allow natural light to fill the space. A wood-burning stove is positioned in the corner, and an easel displays a vibrant painting. A plush rug adds warmth to the wood floor.
Home in Craryville
4.98 out of 5 average rating, 222 reviews

Modern Home in Woods w/ Hot Tub 10 Miles to Hudson

EricRating, 5 starstoday
A quiet private property located close to amenities, the city of Hudson, and nature. It is a beautiful and comfortable home filled with creative and tangible care. We enjoyed cooking in the kitchen and spending time on the property over a long weekend stay.
Top guest favorite
A charming red farmhouse is set against a backdrop of rolling hills and blue skies. The property includes a separate red building nearby, surrounded by lush green grass and a landscaped stone garden featuring colorful flowers and greenery.
Home in Colrain
4.94 out of 5 average rating, 179 reviews

Secluded Farmhouse Retreat - stunning views

ColinRating, 5 stars2 weeks ago
We were four retired couples. Worldly travelers used to very comfortable surroundings. No TV was fine for this occasion. The farmhouse is designed with furniture comfortable for all, appointed in a farmhouse motif, of course, but the design aesthetic is of a quality respectful of its guests. "Good enough", never is. Obviously, the quality of consideration our Host has for the farmhouse presentation is treat your guest with respect and it will be reciprocated. One of the individuals commented, prior to even unpacking: "Perfect Place!" While it rained, we did not have the opportunity to enjoy the firepit, but some enjoyed the Hot Tub, as we all talked late into the night. This is located "close enough", 10 min drive to "civilization", to sites and shopping but it's really a more slightly secluded, private environment whereby a large family or, like us, distinct families can share comfortably, "come and go" separately together or stay together, together. We enjoyed ourselves.
Superhost
A charming farmhouse is depicted, featuring a white exterior and a welcoming red front door. Windows provide natural light, and a wood pile is neatly stacked beside the entrance. Lush greenery and seasonal foliage surround the home, set against a clear blue sky.
Home in Northampton
4.88 out of 5 average rating, 638 reviews

The Farmhouse - Hot tub eclectic farmhouse 3 br

AngieRating, 5 stars1 month ago
This is our second time staying in The Farmhouse, and our 5th or 6th time booking with Ginny. This property is very relaxing, we brought our three dogs and they loved the backyard. The house was clean and organized. We enjoyed breakfast on the farmers porch. The hot tub was nice. It’s a quick drive to downtown NoHo, Florence and EastHampton. So much to do in this area. We highly recommend.
Top guest favorite
The spacious A-frame home is set against a backdrop of vibrant trees and lush greenery. A well-manicured hill leads to the house, which features large windows allowing natural light to fill the interior. The bright blue sky complements the tranquil outdoor scenery.
Chalet in Dover
4.97 out of 5 average rating, 113 reviews

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

CaterinaRating, 5 stars3 months ago
Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.
Superhost
A rustic living space features wooden beams and warm, ambient lighting. An antique stove serves as a focal point, surrounded by comfortable seating and a wooden table. Shelves filled with various items add character to the cozy atmosphere.
Cabin in Londonderry
4.81 out of 5 average rating, 477 reviews

Stunning Rustic Apple Barn - hot tub & sauna

ChristianRating, 5 stars1 week ago
We had a wonderful stay! It's such a beautiful and unusual cabin. It would be great for two couples as there are 2 equally great bedrooms that are quite separate, and a very nice sitting area around the amazing wood stove. (Which we didn't use because it's June and not necessary.) The hot tub was such a treat, and the bedroom with the boat was so cool. (OK, so maybe the bedrooms aren't quite equally great.) The kitchen is outstanding! We sat out on the porch a lot looking over the meadow, and I really liked that we were able to bring our dog. About the notes and instructions: they didn't bother us at all. There's a few non-intuitive features of the cabin, and it was useful to have clear guidance on those things. I want to make clear why I gave 4 stars for "cleanliness". I think they do an excellent job cleaning this cabin! But a rustic cabin like this is impossible to make "5-star clean". If you want or need that level of cleanliness, then "rustic" isn't for you! Go find a nice hotel.
Top guest favorite
An open-concept kitchen features a central island with bar seating for two, surrounded by wooden cabinetry and ample natural light from large windows. A dining area with a table for six is visible, complemented by wooden chairs and a cozy living space in the background, showcasing a comfortable setting.
Home in Newfane
4.98 out of 5 average rating, 136 reviews

Peaceful cabin close to skiing & Brattleboro

MarinaRating, 5 stars3 months ago
This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.
Guest favorite
The exterior showcases a rustic wooden building surrounded by lush greenery and vibrant shrubs. A winding stone path leads to the entrance, while large glass doors provide a welcoming view into the interior. The setting is serene and integrated with nature.
Apartment in Londonderry
4.96 out of 5 average rating, 582 reviews

Vermont Getaway Apartment

AshleyRating, 5 stars1 week ago
The getaway apartment was just as described. Peaceful, private, and with ample space and amenities for a family of three. We enjoyed our weekend!

Family- and pet-friendly home rentals

Top guest favorite
Home in Dummerston
4.99 out of 5 average rating, 347 reviews

Pinecone Pond

KathyRating, 5 stars2 weeks ago
We had the most lovely stay at Pincone Pond. The house is absolutely spotless and well stocked with everything you need in the kitchen, shampoo and condition in the bathrooms and throw blankets for the cool evenings. The house is so homey and comfortable and the grounds are stunning. Beautiful yard and pond which were well cared for. Catherine has thought of everything including chairs for sitting by the pond or fire pit. Just a lovely, peaceful spot.
Guest favorite
The entrance to a rustic blue cottage is framed by a well-maintained lawn, lined with greenery. A short pathway leads to the front door. The deck area features a gas barbecue and is partially shaded by trees in the background.
Cabin in Brattleboro
4.89 out of 5 average rating, 499 reviews

Cottage

LizRating, 5 stars5 days ago
A great spot, only a short drive from downtown Brattleboro. The host was friendly and responsive. It’s a lovely cabin and the surrounding nature is very peaceful. It’s a cozy, quiet spot.
Top guest favorite
A bright interior is featured, showcasing a mix of seating options including a blue sofa and an upholstered armchair. A small dining table is complemented by wooden chairs. The kitchen area is visible, equipped with diverse utensils, while large windows on two sides allow natural light to fill the space.
Apartment in Andover
4.98 out of 5 average rating, 429 reviews

Private Hilltop farm apartment

WillowRating, 5 stars3 weeks ago
What a lovely and serene spot to spend a few days in the Mountains of Vermont! Loved waking up to views of horses in the field by the private deck and a breathtaking mountain view. The hosts were kind and communicative. The space was clean and had just the right amount of amenities. Definitely recommend and hope to stay again!
Top guest favorite
Barn in Guilford
4.99 out of 5 average rating, 126 reviews

The Carriage Barn

AristidesRating, 5 stars2 weeks ago
We really enjoyed our stay here. The place is incredible, you’ll have everything you’d need. Full of very thoughtful details. Very cozy, confortable and charming. The surroundings are beautiful and in a short drive you’d find anything you may need in Brattleboro. From dining to great coffee, groceries and more… I loved how simple and easy where the instructions for check-in and Out. Katherine was very friendly and responsive. Would definitely stay there again.
Guest favorite
The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.
Tiny home in Jamaica
4.94 out of 5 average rating, 1,273 reviews

Apple Blossom Cottage: A Tiny House

AmyRating, 5 stars4 days ago
so beautiful and cozy! private and in just the right location.
Guest favorite
Chalet in Dover
4.92 out of 5 average rating, 307 reviews

A charming VT chalet

carolynRating, 5 stars1 week ago
Mary was a super good hostess and she even left us a welcome basket full of goodies including Bogle red wine (cabernet), coffee, and other treats plus homebred brownies in the fridge! We loved the chalet and the beauty of it inside and out with the greenery of the forest and the brook which our dog, Beau, got right into it and loved it! We all enjoyed the area and the cozy home with the room to spread out and hear the rain as we were snug inside. The bed we chose to sleep in was comfy and warm and I (Carolyn) loved having coffee on the deck of a morning with Beau. We enjoyed our long walks down the road and the town of Dover was fun to visit as well as the beautiful wedding we attended over Wilmington not far away. It was a wonderful stay and we certainly love Vermont! This was our 4th stay in Vermont between the years of 2004 - now. Our first "Dog Vacation" took us to Brattleboro, Middlebury, Willoughvale with Lake Willoughby, and last summer to White River Junction and Barre. Fun!
Superhost
A scenic farmstead is presented, featuring grazing sheep across a grassy field. The structure includes an historic barn surrounded by trees and a fenced garden area. A birdbath stands in the foreground, offering a tranquil farm setting.
Home in Cheshire
4.85 out of 5 average rating, 214 reviews

19th c. Barn in The Berkshires

JohnRating, 5 stars6 months ago
Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.
Guest favorite
An open living area features a dining table surrounded by wooden chairs. A comfortable sofa sits near a coffee table, with an air conditioning unit and a television mounted on the wall. Wooden beams adorn the ceiling, contributing to a cozy atmosphere.
Cottage in Bernardston
4.88 out of 5 average rating, 324 reviews

Cozy, Quiet Cottage on Country rd 2 mil from I-91

JenniferRating, 5 stars1 week ago
This is the second time staying here and look forward to staying here again. Place is easy to get too and always very clean.

Family-friendly home rentals with a pool

Guest favorite
A serene backyard features a heated saltwater swimming pool, surrounded by lounge chairs and a safety fence. Verdant landscapes and a blue sky provide a tranquil backdrop, while a red barn is visible in the distance, adding to the rural charm.
Home in Salem
4.98 out of 5 average rating, 192 reviews

Magical Farm Getaway - a must visit!

BriannaRating, 5 stars2 weeks ago
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!
Guest favorite
An outdoor heated pool is surrounded by a stone patio, furnished with lounge chairs and umbrellas. Lush green grass and neatly trimmed shrubs outline the pool area, complemented by trees and well-maintained landscaping in the background.
Townhouse in Dover
4.96 out of 5 average rating, 148 reviews

Bear's Den - Mt Snow Townhome w/ Heated Pool!

NikkiRating, 5 stars4 months ago
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.
Top guest favorite
A child relaxes on a clear inflatable float in a sparkling swimming pool. Colorful bubbles and additional floats drift nearby, while sunlight reflects brightly on the water's surface. The pool's uniform depth is visible along the sides.
Apartment in Northampton
4.98 out of 5 average rating, 309 reviews

Sunny Inspirit Apartment in best downtown location

LauraRating, 5 stars3 weeks ago
very nice place! we slept very well! comfortable, quiet, relaxing! we would stay there again!
Guest favorite
An indoor pool area is highlighted by a wooden ceiling with exposed beams and large windows that invite natural light. A clean, turquoise pool is surrounded by stone flooring, with seating areas and safety equipment visible. The space features a rustic design, enhancing the recreational atmosphere.
Chalet in Wilmington
4.95 out of 5 average rating, 98 reviews

Rustic Sunny Vermont Home near Mount Snow

AndreaRating, 5 stars3 months ago
Couldn't say enough great things about both the hosts and the property. Just lovely home - very spacious, and clean and cosy. The area is gorgeous, with a lot to do. Mt. Snow and Hermitage skiing are very close, and Wilmington and the area are charming. Host was very gracious and kind..thank you!
Guest favorite
A clear blue pool is surrounded by a sunbathing area featuring white lounge chairs. Lush greenery and trees are visible in the background, providing a natural setting. A fenced area with tall trees enhances the outdoor space for relaxation.
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars2 months ago
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.
Guest favorite
A circular pool is set within a grassy area, surrounded by lush greenery. A shaded picnic area features a large table beneath a white umbrella. Colorful inflatables are visible on the water's surface, adding a playful touch to the serene outdoor setting.
Bungalow in Easthampton
4.92 out of 5 average rating, 505 reviews

The Creation Station

ErinRating, 5 stars2 weeks ago
John went out of his way to ensure we had a great stay. It was a great place that accommodates many and the hot tub was relaxing after a long day of golf.
Top guest favorite
The living room is furnished with a blue sofa and a light armchair, complemented by wooden side tables and lamps. A coffee table is positioned centrally on a carpeted floor. Walls are adorned with wood paneling and artwork, enhancing the space's rustic charm.
Townhouse in Dover
4.94 out of 5 average rating, 81 reviews

Cozy Bear- 1 mile to Mt Snow Ski Home

KimberlyRating, 5 stars1 month ago
We really loved staying here. The location was perfect and the accommodations were fantastic. Our host was exceptional in making sure we were comfortable and informed. We will definitely try to book again.
Guest favorite
A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars3 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

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