
Family-friendly vacation rentals in West Windsor
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Top-rated family-friendly rentals in West Windsor
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Popular amenities for West Windsor family-friendly rentals
Family-friendly home rentals with a hot tub

Private Apt. on Farm, Hot Tub with views!
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 of the World! Jacuzzi! Private Hiking Trails!
Nice place thanks Mike

Macintosh Hill Farm
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.

Stunning Rustic Apple Barn - hot tub & sauna
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

Peaceful cabin close to skiing & Brattleboro
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.

Ski Chalet with Hot Tub on Okemo Mountain
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!

Vermont Getaway Apartment
Communication with the hosts was very easy and kind! The place was as described and pictured, it was a lovely little getaway!!

Spacious Renovated Barn Apt on 100 acres!
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

Cozy Vermont Cabin near Okemo.
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.

Beautiful Serene Lake/Ski House with central AC
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!

Apartment on Main Street
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.

Quiet Vermont Farmhouse
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.

Hancock hideaway
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!

A charming VT chalet
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.

Mountain Home ready for you!
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.

The Guest House at Sky Hollow
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

Bear's Den - Mt Snow Townhome w/ Heated Pool!
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.

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

Epic Views of the Green Mountains
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.

Mt Snow Ski In/Out at Seasons
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.

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

Cozy 3BR/2BA Chalet – Mins to Mtn & Biking Trails
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!

One Bedroom Suite Near Okemo
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.

Serene Top Floor Condo (resort style amenities)
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
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- Rentals with a washer and dryer West Windsor
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- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Monadnock State Park
- Owl's Nest Resort
- Pico Mountain Ski Resort
- Pats Peak Ski Area
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Ragged Mountain Resort
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Bromley Mountain Ski Resort
- Autumn Mountain Winery
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Ekwanok Country Club
- Bretwood Golf Course
- Hooper Golf Course