Family-friendly vacation rentals in West Windsor

Find and book unique family-friendly homes on Airbnb

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Popular amenities for West Windsor 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 Plymouth
4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

MichaelRating, 5 stars3 months ago
Nice place thanks Mike
Top guest favorite
Guesthouse in Randolph
4.96 out of 5 average rating, 259 reviews

Macintosh Hill Farm

MadelynRating, 5 stars3 months ago
A wonderful ski weekend! We spent two nights and spent the day (Saturday) skiing at Killington. Quiet drive there and back so it was a perfect location to come back to a peaceful evening. Hot tub was amazing after skiing and very clean! Laura and Aaron were very helpful and let us know the conditions of the roads prior to our arrival. Flexible, kind and friendly! Would stay again for sure.
Superhost
Cabin in Londonderry
4.81 out of 5 average rating, 475 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
Top guest favorite
Home in Newfane
4.98 out of 5 average rating, 136 reviews

Peaceful cabin close to skiing & Brattleboro

MarinaRating, 5 stars2 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.
Top guest favorite
Home in Ludlow
4.97 out of 5 average rating, 159 reviews

Ski Chalet with Hot Tub on Okemo Mountain

MariaRating, 5 stars2 months ago
Our time at Eric’s chalet was amazing. The place was beautiful, peaceful, and extremely well maintained. It was perfect for a relaxing weekend getaway. We were in town for a wedding a few towns over, and coming back to this cozy spot after a night of celebrating was just what we needed. Eric was a super accommodating host. We had a family emergency that delayed our arrival, and he kindly gave us a few extra hours at checkout, which we truly appreciated. The home was exactly as pictured and very clean, with thoughtful touches throughout. The kitchen had everything we needed, and we loved unwinding in the hot tub. The laundry was also a big plus. We have already recommended Eric’s place to friends and would absolutely stay here again. Highly recommend!
Guest favorite
Apartment in Londonderry
4.96 out of 5 average rating, 581 reviews

Vermont Getaway Apartment

NinaRating, 5 stars2 weeks ago
Communication with the hosts was very easy and kind! The place was as described and pictured, it was a lovely little getaway!!
Guest favorite
Loft in Ludlow
4.95 out of 5 average rating, 812 reviews

Spacious Renovated Barn Apt on 100 acres!

MichaelRating, 5 stars2 weeks ago
Tesha's place in Ludlow was exactly what I needed- the rare combination of a private, quiet space in a natural setting which also provides all the comforts of home- and some extra luxuries too! The listing photos don't do it justice and immediately upon arrival it's obvious a lot of effort was put into ensuring the place provides guests a wonderful stay. Next time I need to escape the city I will definitely be checking to see if it's available.

Family- and pet-friendly home rentals

Guest favorite
Cabin in Mount Holly
4.92 out of 5 average rating, 196 reviews

Cozy Vermont Cabin near Okemo.

MarlaRating, 5 stars3 months ago
A very clean, cozy, and comfortable home! We came to ski at Okemo and were pleased that the house is only about a 10 minute drive from the resort and the town of Ludlow where there are great restaurants and shops. The living area of the home is spacious and great for hanging out - there were tons of movies on DVD and video games to enjoy. The kitchen was well-equipped and perfect for cooking meals at home. The beds were comfy. Overall a wonderful stay! We hope to be back in the future.
Guest favorite
Cabin in Grafton
4.86 out of 5 average rating, 220 reviews

Beautiful Serene Lake/Ski House with central AC

TaylorRating, 5 stars4 months ago
Natalia’s home was beautiful! We stayed for a winter ice fishing weekend with a few couples, including dogs and babies. The home was right on the ice, which was perfect for our purpose. There was plenty of space for everyone to spread out and be comfortable. The living room seating was particularly great- everyone always had a comfy spot to sit. We enjoyed our stay!
Superhost
Apartment in Saxtons River
4.83 out of 5 average rating, 185 reviews

Apartment on Main Street

CraigRating, 5 stars1 month 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.
Superhost
Apartment in Taftsville
4.79 out of 5 average rating, 177 reviews

Quiet Vermont Farmhouse

TimRating, 5 stars2 months ago
This is a nice cozy attic apartment inside of a residence. Steep staircase. No living room. Wonderful walking area beside a river. Close to Woodstock and Dartmouth. Gracious host. Temperature a little difficult to regulate. Recommend.
Top guest favorite
Cabin in Hancock
4.94 out of 5 average rating, 252 reviews

Hancock hideaway

MatthewRating, 5 stars1 week ago
Heidi's place is a wonderful cabin in the woods with all you need to enjoy the nature in Vermont. Super peaceful and the property is well maintained. I would highly recommend staying here to enjoy your vacation!
Guest favorite
Chalet in Dover
4.91 out of 5 average rating, 305 reviews

A charming VT chalet

BrentRating, 5 stars3 weeks ago
Needed a home-base for the weekend and Mary’s place was once again (this was our second stay here!) fantastic. Waking up to the sound of the river in the yard from the rainstorm the day before is incredibly special.
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!!

Family-friendly home rentals with a pool

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.
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 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
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!
Guest favorite
Condo in Proctorsville
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
4.78 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!

Quick stats about vacation rentals that are family-friendly in West Windsor

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore