Family-friendly vacation rentals in Brattleboro

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Brattleboro family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Plymouth
4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

MichaelRating, 5 stars1 month ago
Nice place thanks Mike
Guest favourite
Farm stay in Valley Falls
4.89 out of 5 average rating, 224 reviews

Country Getaway Lodge / Ranch

TrevorRating, 5 stars4 months ago
Fantastic space for a large group. We had 10 people for a New Year’s Eve ski weekend, and this was the ideal spot for it. Hot tub was a great treat. Be warned - the floors are squeaky, so if you’re a light sleeper in a large group bring ear plugs.
Guest favourite
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars2 weeks 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 favourite
Chalet in Killington
4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

AudreyRating, 5 stars1 month ago
We could not have found a better home for our Killington ski week. The ski in ski out directions were perfect and so easy. The home comfortably accommodated 8 adults and provided privacy for each of us as well. Fabulous dining area for our family that provided many happy memories. We've never rented a home where every single bed was so luxurious either. Each night we slept so soundly. On days we did not ski there was plenty to do at the house, a beautiful neighborhood to walk in and such close proximity to Killington Rd with so many dining options.
Guest favourite
Condo in Killington
4.97 out of 5 average rating, 144 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

MichaelRating, 5 stars1 month ago
Great spot near the mountain. nice community pool and hot tub.
Top guest favourite
Home in Ludlow
4.97 out of 5 average rating, 158 reviews

Ski Chalet with Hot Tub on Okemo Mountain

MichaelRating, 5 stars1 month ago
Great house, location, and host! Eric was very helpful, communited timely, and is super organized. The house is in a great private location right near Okemo, plenty of restaurants, and a grocery store. The house felt bigger than the square footage states and was perfect for our two families (4 adults and 4 kids aged 9-12). We are usually disappointed in how clean rentals are upon our arrival, but this house was basically impeccable which especially isn't easy in the mountains! The upstairs is perfect for a kids room and the living space was nice and cozy, but didn't feel small. Plenty of room for everyone. I highly recommend this house, the hosts, and Okemo. It was our first time on this mountain and really enjoyed the family friendly atmosphere and terrain while also having plenty of advanced trails as well. Overall we had an A+ weekend.
Superhost
Home in Argyle
4.83 out of 5 average rating, 150 reviews

Expansive Lakehouse with Jacuzzi

MeghanRating, 5 stars8 months ago
My family and I had a wonderful time! Larry is very sweet, gave us a tour, offered to help with docking our boat and even offered my husband the tools to fix the bunk on our trailer. The house is big and beautiful!! Very clean, the beds are comfortable, the kitchen has everything you need!! The hot tub is definitely a bonus as we used it everyday!! The dock was perfect, we had room for our pontoon boat and jet skis. All around the perfect place for some R&R!!! My family and I love Cossayuna Lake as we are semi local and it was our first experience with an Airbnb. Thank you Larry for sharing your home!! Highly recommend this for your next vacation!!
Superhost
Apartment in West Townshend
4.9 out of 5 average rating, 342 reviews

Private Apt on Farm, Hot Tub with views!

EmilyRating, 5 stars1 month ago
We had an amazing stay! The beds were comfy. There is a local grocery store near by. We went snowboarding at Mt snow which was about a 25 min drive - not bad at all! The hot tub was perfect and the views were stunning. We loved Robert’s Glass blowing class as well.

Family- and pet-friendly home rentals

Superhost
Farm stay in West Brattleboro
4.94 out of 5 average rating, 132 reviews

Lilac Ridge Farm House

MatthewRating, 5 stars4 months ago
We had a great stay at Lilac Ridge! The house was near and spacious, plenty of room for our family. We stayed in quite a bit and enjoyed the farm (including a visit with the calves!) and the house. The little farm stand had some nice things, including fresh eggs, maple syrup, honey, and soap, all local. Ross and Amanda were super responsive and took care of all our needs. Thanks so much!
Top guest favourite
Apartment in Northampton
4.95 out of 5 average rating, 241 reviews

Cedar Wet Room w Soaking Tub

AlexRating, 5 stars3 months ago
It was very peaceful, great get away from the city. Good for the dogs. The copper tub is amazing, we could not get enough of it. And the dual showers felt so good. It felt very homey. Mr. John was a a great host.
Guest favourite
Cabin in Ghent
4.9 out of 5 average rating, 283 reviews

Guesthouse close to hiking, shopping and ski!

ReedRating, 5 stars1 month ago
We truly had a fantastic stay at Donna's quaint guesthouse in Ghent! The lovely cabin and many available amenities had everything we could have asked for, and more! Donna was extremely welcoming, kind, and communicative, providing us with clear information for the check-in/out process and going the extra mile to offer local recommendations to make us (including our pup) feel at home during our time away. We would certainly go back in a heartbeat!
Superhost
Home in Otis
4.94 out of 5 average rating, 144 reviews

Berkshires hideaway! Hikes & serenity near lake

MaryRating, 5 stars4 months ago
Niki and Adam’s place was wonderful! Space for everyone, well equipped, comfortable and clean. Communication responses were quick and clear. All 3 generations of my family thoroughly enjoyed their home and its surroundings. Highly recommend!
Guest favourite
Cabin in Danby
4.89 out of 5 average rating, 296 reviews

April/May special So Vt Cabin Mt Tabor Treasure

MelissaRating, 5 stars1 month ago
A great escape. We enjoy our stays here. We are booked again in June. Lori is so attentive. She is always one step ahead. Thank you! 😀
Guest favourite
Tiny homes in Jamaica
4.94 out of 5 average rating, 1,259 reviews

Apple Blossom Cottage: A Tiny House

AveryRating, 5 stars1 day ago
I found this listing years ago while scrolling for tiny houses and it stayed in the back of my mind. I finally had the opportunity to visit as a getaway for my birthday. It was SO peaceful and lovely. I really enjoyed walking the grounds with my dog in lieu of taking a hike nearby, since there was so much rain during my stay. Dominic even let me take a walk to his other property, which was so spacious and pretty as well! I spent most of my time journalling and getting clarity while sitting in the swing on the porch, listening to the rain. I also took a brief voyage to Manchester Center, which was a darling town with lots to explore. I recommend Depot 62 for super tasty Turkish food. The cottage had all the essentials and clear instructions. It could use a deep clean in some of the nooks and crannies, but was overall very tidy and well-kept. I would 100% come back. The vibe up there in the misty mountains of VT is just so high and so freeing. Such a re-aligning stay.
Top guest favourite
Home in New Salem
4.89 out of 5 average rating, 215 reviews

Stone n' Sky Lodge

JasonRating, 5 stars5 months ago
I genuinely don't know what to say other than the fact that this may be one of the greatest places I've had the honor to lodge at. I did a lot of vetting across New England to find a wonderful place that could sleep a decent amount of people, provide a scenic and comfortable escape, and keep us entertained. Sarah's wonderful Stone and Sky Lodge exceeded every expectation I just listed. It's cozy, warm, and feels like a hidden nook! The scenery and nature couldn't be more beautiful. I never got the pleasure to meet Sarah, though I wish I did. Over messages and from what my friends told me, I just know that Sarah is the most hospitable and kind host that I've talked with in a while, and I hope that next time I can thank her personally. From my friends and I, we thank you for sharing your home with us. If you think that the excellent reviews are too good to be true, don't. This IS the truth, and I can't wait to have another reason to come back to this wonderful treasure of a place.
Superhost
Home in Cavendish
4.83 out of 5 average rating, 151 reviews

Okemo-Ludlow, fireplace, hottub, sleeps 13

LilyRating, 5 stars1 month ago
My friends and I had a great time at this place! The home was beautiful and very spacious - we were able to all hang out in the hot tub, kitchen, living room, and no place felt cramped.

Family-friendly home rentals with a pool

Guest favourite
Townhouse in Dover
4.96 out of 5 average rating, 148 reviews

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

NikkiRating, 5 stars2 months ago
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.
Superhost
Condo in Killington
4.92 out of 5 average rating, 106 reviews

Right at Killington !

CrossanRating, 5 stars2 months ago
Our family had a wonderful stay at the condo in Killington. The location could not be beat! A very short 5 minute walk to the lifts and Snowshed lodge. The complex had an amenity building with pool/hot tub that the kids loved and the condo was quite spacious and clean. Ruslana was a great host and very responsive! There is a solid chance we will be back next year!
Guest favourite
Condo in Killington
4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

PatriciaRating, 5 stars1 month ago
This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!
Guest favourite
Guesthouse in Granville
4.9 out of 5 average rating, 896 reviews

Moon Valley Country Retreat no clean fee pets yes

AmberRating, 5 stars1 week ago
There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.
Guest favourite
Condo in Ludlow
4.93 out of 5 average rating, 110 reviews

One Bedroom Suite Near Okemo

ChristopherRating, 5 stars3 weeks ago
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.
Superhost
Condo in Killington
4.8 out of 5 average rating, 107 reviews

*Killington Summer Rental: 3 Bdrm, 2 Bth*

MikeRating, 5 stars2 months ago
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!
Superhost
Condo in Killington
4.78 out of 5 average rating, 307 reviews

Serene Top Floor Condo (resort style amenities)

JonRating, 5 stars1 month ago
A wonderful place situated close to the mountain. The amenities were fantastic as well. The only issue was getting the right pin to access the apartment...however Scott responded within seconds so it was minimally disruptive.
Guest favourite
Condo in Hancock
4.85 out of 5 average rating, 151 reviews

Cozy Condo @ Jiminy Peak

ElizabethRating, 5 stars2 months ago
We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.

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