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
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
Top guest favorite
Guesthouse in Randolph
4.96 out of 5 average rating, 259 reviews

Macintosh Hill Farm

MadelynRating, 5 stars1 month 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.
Guest favorite
Chalet in Killington
4.84 out of 5 average rating, 250 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

MauraRating, 5 stars3 weeks ago
Nice space for a group, plenty of room for dining and relaxing. Clint was very responsive and gave excellent instructions. Appreciated the hospitality!
Guest favorite
Chalet in Ludlow
4.94 out of 5 average rating, 126 reviews

Okemo Ski Chalet with Hot Tub

KatieRating, 5 stars4 weeks ago
Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!
Superhost
Home in Pittsfield
4.84 out of 5 average rating, 238 reviews

Killington area home - 4-seasons & hot tub

KenleyRating, 5 stars1 month 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!
Guest favorite
Condo in Ludlow
4.93 out of 5 average rating, 110 reviews

One Bedroom Suite Near Okemo

ChristopherRating, 5 stars1 week ago
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.
Top guest favorite
Home in Newfane
4.98 out of 5 average rating, 136 reviews

Peaceful cabin close to skiing & Brattleboro

MarinaRating, 5 stars1 month 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
Chalet in Stockbridge
4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

ZachRating, 5 stars1 month ago
Great place to stay! The hot tub after a long day of snowboarding was amazing. Dean responds fast to any questions you have too. Definitely recommend

Family- and pet-friendly home rentals

Guest favorite
Cabin in Jamaica
4.88 out of 5 average rating, 112 reviews

Cozy Log Cabin near Stratton/Mt. Snow-pet friendly

JamesRating, 5 stars1 month ago
Christina was an excellent host who ALWAYS responded to any of my questions or concerns immediately and courteously. Her space was exactly as described and very spacious as well as a fantastic environment for a group to get together and have a great time! I highly recommend Christina’s place for a great time with a large group, she is the ideal host who works tirelessly to provide an amazing space for her guests!
Guest favorite
Cabin in Woodstock
4.95 out of 5 average rating, 198 reviews

Hideaway Cabin by the Stream on 27 Acres

JordanRating, 5 stars7 months ago
We had an awesome getaway at Kevin and Lesley’s cabin! This was our last little getaway before we get married this fall and it was the perfect unplugged retreat to feel connected going into the stressful time before the wedding. The cabin is cozy, the bathroom is adequate and sort of surprisingly not as buggy as it could have been, and the porch was my favorite spot to feel connected to nature. Kevin was very communicative and the instructions in the cabin were very clear. Luce’s lookout was amazing at the top and a really great recommendation by our hosts. We would definitely go back!
Superhost
Apartment in Town of Rockingham
4.83 out of 5 average rating, 182 reviews

Apartment on Main Street

WinnieRating, 5 stars4 weeks ago
This was a very spacious and cozy spot! A perfect place for a quiet weekend getaway with proximity to hiking and/or skiing/snowboarding. There were many books, games, and puzzles available to peruse and enjoy as well.
Superhost
Apartment in Taftsville
4.79 out of 5 average rating, 177 reviews

Quiet Vermont Farmhouse

TimRating, 5 stars2 weeks 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.
Guest favorite
Home in Goshen
4.84 out of 5 average rating, 285 reviews

Nature Lover's Paradise

RobertRating, 5 stars6 days ago
We always love staying here. It’s so peaceful and the sound of the brook is so relaxing! Philip responds quickly and is an excellent host!!
Guest favorite
Cabin in Danby
4.89 out of 5 average rating, 295 reviews

April/May special So Vt Cabin Mt Tabor Treasure

FavyanRating, 5 stars1 month ago
Second time staying here to hike the area trails. The place was immaculate as was my first visit. The hosts are wonderful and helpful. They gave me check in flexibility that added a lot of time to my plans for the day that ended up being a big value. Highly recommend.
Guest favorite
Tiny home in Jamaica
4.94 out of 5 average rating, 1,256 reviews

Apple Blossom Cottage: A Tiny House

JulieRating, 5 stars5 days ago
We enjoyed our stay at Domenic with 2 kids on school break! The tiny house is just as described, colorful, well organized and very comfortable. We enjoyed making a fire outside on a beautiful spring evening and checking out the peacocks!
Guest favorite
Home in Rochester
4.95 out of 5 average rating, 196 reviews

The McKinley House

GarethRating, 5 stars2 months ago
We had a great stay, lovely welcoming home and great location - short walking distance to nice places in town and 30min drive to either Sugarbush or Killington/Pico. Thank you!

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

Cozy, spacious, 3 bedrooms, 4 beds, 5 mi to K Rd.

JoshRating, 5 stars1 month 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
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!
Superhost
Home in Surry
4.7 out of 5 average rating, 44 reviews

Bright, Large, Spacious Family Home

MaryRating, 5 stars5 months ago
We had a very relaxing stay. Plenty of space to stretch out. Located within 10-15 min. of Keene State activities, the purpose of our trip. Bryan was a wonderful host. Very responsive. Instructions were clear, directions very helpful. Everything we needed!!
Superhost
Condo in Killington
4.8 out of 5 average rating, 107 reviews

*Killington Summer Rental: 3 Bdrm, 2 Bth*

MikeRating, 5 stars1 month 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
4.82 out of 5 average rating, 257 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

ZacharyRating, 5 stars2 months ago
Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.
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.

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

  • Total rentals

    50 properties

  • Nightly prices starting at

    $90 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