Family-friendly vacation rentals in Plymouth

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Plymouth family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Apartment in Townshend
4.94 out of 5 average rating, 239 reviews

Private Apt. on Farm, Hot Tub with views!

MathildeRating, 5 stars1 week 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!
Guest favorite
Home in Ludlow
4.87 out of 5 average rating, 196 reviews

2 Doors Down - Modern Farmhouse in Downtown Ludlow

ElaineRating, 5 stars2 weeks ago
We are fishermen from CT who stay at Bob’s place every year. This place accommodates us comfortably. We are able to walk to restaurants and love the location. Bob is so proactive making our stay so easy. He always communicates well and responds quickly to our needs. Until next year.🎣
Guest favorite
Chalet in Killington
4.84 out of 5 average rating, 251 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

ScottRating, 5 stars2 weeks ago
This is our second time renting Clinton's ski lodge place is great super host. Always responsive will be renting again next season.
Guest favorite
Condo in Killington
4.95 out of 5 average rating, 105 reviews

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

PatriciaRating, 5 stars2 months 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!
Superhost
Home in Pittsfield
4.84 out of 5 average rating, 238 reviews

Killington area home - 4-seasons & hot tub

KenleyRating, 5 stars3 months ago
We had a great time at David's place. The kitchen was well stocked, plenty of firewood, and the hot tub was ready to go. The house was very clean. All the bedrooms had plenty of linens, and extra blankets. We would definitely stay at David's again!
Superhost
Cabin in Londonderry
4.82 out of 5 average rating, 474 reviews

Stunning Rustic Apple Barn - hot tub & sauna

MasonRating, 5 stars2 weeks ago
Absolutely great place to stay Ben was a great host and I really appreciated the way he had everything laid out and straight forward. Would absolutely go back anytime. If you want to get away for a peaceful relaxing time it can’t be beat. Cooking a great meal in the awesome kitchen then being able to relax in the hot tub
Superhost
Condo in Killington
4.78 out of 5 average rating, 308 reviews

Serene Top Floor Condo (resort style amenities)

NikitaRating, 5 stars2 weeks ago
Amazing view and cozy vibes. Hot tub and a pool are fun amenities to have. Building has freshly renovated pool and tubs. If you like it there are also sauna pods. So do not forget your swimsuit. It was clean and if you cook there is a kitchen. On top of that it was great to have a balcony with a view. May is a nice time to come even if you are not skiing because it’s not crowded and nature is stunning. And there are plenty of spots for mountain bike. Scott is a great host and local recommendations are helpful and honest. Visit liquid art, if you want a good cup of coffee that’s the right place. Great place!
Guest favorite
Condo in Killington
4.97 out of 5 average rating, 144 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

MichaelRating, 5 stars2 months ago
Great spot near the mountain. nice community pool and hot tub.

Family- and pet-friendly home rentals

Superhost
Guest suite in Fairlee
4.88 out of 5 average rating, 187 reviews

Cloud 9 Private Suite Retreat

KevinRating, 5 stars2 days ago
The apartment was impeccably, clean! Beautiful views. Amanda was fantastic in helping me find my way around to where I needed to go. Highly recommend it.
Superhost
Apartment in Town of Rockingham
4.83 out of 5 average rating, 185 reviews

Apartment on Main Street

CraigRating, 5 stars4 weeks ago
We have family in Springfield so staying at Whitney and Alex’s place is perfect for us. It’s spacious and comfortable. This was our second stay and we will definitely be returning.
Top guest favorite
Cabin in Hancock
4.94 out of 5 average rating, 251 reviews

Hancock hideaway

BRating, 5 stars1 month ago
We enjoyed staying in Heidi's Hancock Hideaway! We enjoyed the peaceful, quiet & comfortable place. We enjoyed taking walks, sitting on the porch during the day & star gazing at night. Kitchen had everything we needed to make & enjoy our meals. Heidi made sure we had clear directions with perfect details to arrive at the Hideaway. We even had fun staying in and doing puzzles during the rainy days. Our dog enjoyed laying in the sunshine outside & in front of the windows. Local recommendations were great.
Superhost
Chalet in Stockbridge
4.84 out of 5 average rating, 158 reviews

Vermont Chalet

JugoRating, 5 stars3 weeks ago
Great little cabin. My wife and I had an amazing time. We really enjoyed both decks and the fire pit by the pond. We will be back for sure. It’s located in between some great Vermont towns.
Guest favorite
Home in Rochester
4.91 out of 5 average rating, 295 reviews

Mountain Home ready for you!

ShannaRating, 5 stars3 months ago
My friends and I had a great stay at Jennifer’s home. We wanted a winter escape from the city and got exactly that! Jennifer was super friendly and communicative and left no questions unanswered. The home was so welcoming and cozy and had everything we needed for a fun weekend.
Guest favorite
Home in Rochester
4.98 out of 5 average rating, 205 reviews

The Guest House at Sky Hollow

JasonRating, 5 stars1 month ago
This is my second time staying at one of Jess’s properties - and I’m sure it’s not my last. The property is beautiful inside and out and has everything you need. I was in town for a full week and this place was just what I needed to relax after long work days. I can’t recommend staying at one of Jess’s places enough. You won’t regret it!!
Top guest favorite
Cabin in Pawlet
4.94 out of 5 average rating, 155 reviews

Hickory Ridge, Vermont Log Cabin, no cleaning fee

MitchRating, 5 stars2 days ago
Truly unlike anywhere I’ve ever stayed. I can’t recommend this home enough. The pictures do not do the property justice. You will not regret staying here!
Guest favorite
Home in Cavendish
4.93 out of 5 average rating, 104 reviews

Renovated Vermont Schoolhouse – Close to Okemo

ChrisRating, 5 stars3 months ago
Marianne was so responsive and kind. The place is super close to Okemo. The space is probably bigger than it looks like in the photos. Super quiet secluded spot. Kitchen was nice and big for us to cook for a troop of hungry skiers. Thought this was a really nice family oriented spot. Second time we have stayed there and hope we can come back there for more ski trips!

Family-friendly home rentals with a pool

Guest favorite
Home in Salem
4.98 out of 5 average rating, 191 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars3 months ago
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!
Guest favorite
Townhouse in Dover
4.96 out of 5 average rating, 148 reviews

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

NikkiRating, 5 stars3 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 stars3 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 favorite
Guest suite in Killington
4.95 out of 5 average rating, 145 reviews

Cozy, spacious, 3 bedrooms, 4 beds, swimming pool.

JoshRating, 5 stars2 months ago
Amazing stay. Loved how close it was to the mountain. The pool also looked amazing so sad it was winter. Definitely recommend staying there were 4 beds and can comfortably fit 5-6 people.
Guest favorite
Home in Granville
4.96 out of 5 average rating, 145 reviews

Epic Views of the Green Mountains

ColbyRating, 5 stars1 week ago
We had a great stay at William’s. The location was beautiful and the house was comfortable. We had a great mix of day-tripping and relaxing with a view. We also ran into William and he was very helpful and friendly.
Guest favorite
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars1 month 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
Condo in Ludlow
4.93 out of 5 average rating, 110 reviews

One Bedroom Suite Near Okemo

ChristopherRating, 5 stars1 month 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

Cozy 3BR/2BA Chalet – Mins to Mtn & Biking Trails

MikeRating, 5 stars3 months ago
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!

Quick stats about vacation rentals that are family-friendly in Plymouth

  • Total rentals

    140 properties

  • Nightly prices starting at

    G$18,882 GYD before taxes and fees

  • Total number of reviews

    5.4K reviews

  • Pet-friendly rentals

    60 properties allow pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    140 properties include access to wifi

Destinations to explore