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Vacation rentals in Winhall

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Top-rated vacation rentals in Winhall

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Wilmington

5 out of 5 average rating, 8 reviews

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

DevonRating, 5 stars3 months ago
Our family has been going to VT in the fall for 25+ years. The usual house we stay in was unavailable and lead us to find this home. Upon arrival we were stunned at the view, it is incredible in person! We had 5 adults and two children o this trip and this home offered us so much space and activities. My father even noted how everyone had their own space to dow whatever they wanted at any point in the day. We utilized the amenities every day and my kids were thrilled to have all the games to play inside as well as a beautiful lawn to run around and play on. Just a short drive down the driveway you reach the water which we also utilized mulitple times a day. Overall it was very peaceful and felt like a retreat and now my kids prefer this house over the old one! Definitely hoping to come back soon! Also, the hosts were very communicative and responsive before and during our stay, we very much enjoyed our time.
Guest favorite

Home in Cavendish

5 out of 5 average rating, 40 reviews

Okemo <12 min Game room~Hot tub~Fire pit~Mtn Views

GinaRating, 5 stars2 weeks ago
Julie was a wonderful host and her home is absolutely lovely! Plenty of great amenities to keep everyone happy and busy. Amazing family weekend getaway home! Thank you to Julie for sharing your home with us.
Superhost

Apartment in Pownal

5 out of 5 average rating, 8 reviews

"The Triple Chambers"

MarthaRating, 5 stars48 months ago
Place is going thru renovation so we got to our second floor apartment via steep and narrow stairs which could a problem for someone. Three spacious bedrooms and very clean and spacious bathroom. We absolutely loved the place.
Guest favorite

Home in Hoosick Falls

4.91 out of 5 average rating, 11 reviews

Enjoy Fall & Experience Beautiful Changing Colors

AshleyRating, 5 stars4 months ago
Would highly recommend this beautiful spot!!! We loved the peaceful location and space for our entire family with the comforts of home in each room. Lots of extra pillows, towels, blankets, etc. fully stocked kitchen too. My kids wanted to stay longer, they had a great time. We will certainly come back!!
Guest favorite

Home in Poultney

4.89 out of 5 average rating, 9 reviews

Snowberry Farm Home Sweet Home

AudreyRating, 5 stars3 months ago
We enjoyed our stay at Valerie’s. The house was spacious and comfortable. Loved the peaceful location. Thank you!
Guest favorite

Apartment in Wilmington

4.91 out of 5 average rating, 129 reviews

Globetrotter Retreat too - Minutes to the Mountain

RichardRating, 5 stars6 days ago
This is our second stay at this location (different apartment in same building) and it was very centrally located and close to Mount Snow. This is a great place to stay in Wilmington.
Guest favorite

Cottage in Fair Haven

4.92 out of 5 average rating, 151 reviews

Historic Cottage 2 Bedroom 2 Bath Fast Wifi

PaulRating, 5 stars4 days ago
Our stay was pleasant, and the space was very clean and cozy. Great deal for the price. Excellent communication and instructions and if I find myself back in the area I'd gladly book with Craig again!
Guest favorite

Villa in Pownal

4.94 out of 5 average rating, 66 reviews

Vermont Vacation Villa—Grapevine Getaway

DavidRating, 5 stars2 days ago
A GREAT stay! We had a family weekend away here, the place was big enough to fit all of us with plenty of space. There is a TON of space in this home with large rooms! The great room has a beautiful view of the scenery, kitchen is well stocked with the essentials, and garage was great to keep ski gear in while we were not at the mountain. Would highly recommend staying here and our family would love to return!
Guest favorite

Condo in Stratton

5 out of 5 average rating, 12 reviews

Top Flr Duplex 3BR 4BA - Walk to All @ Stratton Mt

ScottRating, 5 stars1 month ago
A great spot. Very comfortable. Exactly as described in the listing. Easily accessible to the base by either a 10-15 minute walk or a frequent shuttle that leaves from the garage in the building. Very clean. Well appointed kitchen (we cooked all our meals in). Very helpful building staff. Would definitely stay again.
Superhost

Home in Readsboro

4.86 out of 5 average rating, 125 reviews

December in Peaceful Vermont (Pet Friendly)

JudahRating, 5 stars1 month ago
This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.
Guest favorite

Home in Wilmington

5 out of 5 average rating, 25 reviews

Kiki's Mountain Chateau

AmyRating, 5 stars1 week ago
Had a weekend stay here and couldn’t have asked for a better place. Biggest thing is make sure you have AWD/4WD as the roads around are dirt roads and very snowy. My jeep however loved it. Very convenient commute to Mount Snow.
Guest favorite

Apartment in Williamstown

5 out of 5 average rating, 118 reviews

Downtown | Waterfront | Walk to Shops

JamelleRating, 5 stars3 weeks ago
I had an excellent time staying in Williams’ place. It was easy to find easy to get into and very convenient. Would highly recommend.

Popular amenities for Winhall vacation rentals

Stay near Winhall's top sights

Stratton Mountain Resort173 locals recommend
Bromley Mountain Ski Resort187 locals recommend
Johnny Seesaw's49 locals recommend
Mulligan's43 locals recommend
Red Fox42 locals recommend
Winhall Market38 locals recommend

Other great vacation rentals in Winhall

Guest favorite

Home in Wilmington

5 out of 5 average rating, 10 reviews

Countryside SKI Retreat - Indr Pool&HotTubGameRoom

PhillipRating, 5 stars2 weeks ago
This was a great place for a family get away. Right in the middle of Southern VT ski country. Easy to get to both the Mount Snow area and downtown Wilmington. Club house at Chimney Hill was awesome. We utilized the fitness center each day and there were plenty of people enjoying the indoor pool. We also had a chance to do some ice skating. The house had plenty of room and we had a great time just gathering near the fireplace and watching the snow fall. Shannon and Erika were great hosts and let us know what to expect every step of the way. We look forward to returning to the area and making more memories with our family.
Guest favorite

Condo in Dover

5 out of 5 average rating, 10 reviews

Cozy condo with direct mountain views and shuttle

EliRating, 5 stars2 weeks ago
This is a great place to stay with family to ski at Mount Snow. The Moover bus is just out the door (runs a bit faster then every 20 minutes). Two nice bed rooms and bathrooms. Nice living room and kitchen and great view. Already booked to go back!
Guest favorite

Townhouse in Winhall

4.96 out of 5 average rating, 23 reviews

New! Vermont Getaway! Stratton - close to skiing!

CarolineRating, 5 stars4 months ago
Conveniently located in the center of beautiful, forested mountains, this condo was easy, cozy and comfortable. We stayed for a fall weekend and enjoyed ourselves so much. Anthony was very communicative. We can’t wait to visit again!
Guest favorite

Home in Monroe

4.92 out of 5 average rating, 13 reviews

The Camp

BrendaRating, 5 stars1 day ago
We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!
Superhost

Home in Manchester

4.85 out of 5 average rating, 34 reviews

Your VT Ski House: Fireplace, Indoor Pool, Dogs

KaylaRating, 5 stars11 months ago
melissa was very responsive and even sent help when we needed heater :) nice house for a family gathering, our group had a great time!!
Superhost

Townhouse in West Dover

4.74 out of 5 average rating, 19 reviews

Beautiful 4 Bedroom Townhome Minutes from Mt Snow

UtsavRating, 5 stars2 months ago
Great place for 10 with nice surroundings and close to cafe, restaurants and brewery. Perfect 2 days trip place. Jacuzzi and sauna also good add ons to mention.
Guest favorite

Home in Dover

4.88 out of 5 average rating, 66 reviews

Large Mount Snow Ski House with Hot Tub

JamesRating, 5 stars1 month ago
10/10 will be returning next year! The house is huge with so many beds. There’s so much to do in the house from the board games to the rec room downstairs to the hot tub. Great Airbnb very clean !
Guest favorite

Home in Wilmington

4.87 out of 5 average rating, 101 reviews

MtSnow * Hot Tub * Pool * Air Hockey * PingPong * Darts * 16ppl

AkhilRating, 5 stars2 days ago
The place was amazing. It was what the pictures show plus much more. Me and 10 of my friends slept comfortably and had a great time. Many games, nice kitchen, clean rooms and bathrooms, and if you’re a winter lover, hope it snows because this yard is amazing. We went sledding like kids again it was great. Definitely recommend. Right near mt. Snow and town of Wilmington which has great food options. Overall, quite the memorable stay.

Quick stats about vacation rentals in Winhall

  • Total rentals

    320 properties

  • Nightly prices starting at

    ﺩ.ﺇ404 before taxes and fees

  • Total number of reviews

    7.5K reviews

  • Family-friendly rentals

    270 properties are a good fit for families

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    50 properties have a pool

Frequently Asked Questions

  • Are there Winhall townhouse rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 townhouse rentals with pools in Winhall, available on Airbnb. Make a splash and soak up the sun in style!

  • Do condo rentals in Winhall have wifi?

    Absolutely! We offer over 30 condo rentals with wifi in Winhall. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Winhall?

    Experience the best of Winhall with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly vacation rentals in Winhall?

    Winhall has more than 260 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do cabin rentals in Winhall have air conditioning?

    Absolutely! We offer over 10 cabin rentals with air conditioning in Winhall. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Winhall?

    Yes! Work meets play with ease at over 150 vacation rentals in Winhall featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do chalet rentals in Winhall have free parking?

    Absolutely! We offer over 30 chalet rentals with free parking in Winhall. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Winhall have a kitchen?

    Absolutely! We offer over 20 cabin rentals with a kitchen in Winhall. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Townhouse Rentals in Winhall?

    Enhance your stay in our Townhouse Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with free parking, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there pet-friendly vacation rentals in Winhall?

    Four-legged friends are welcome in Winhall. Choose from more than 120 vacation rentals for guests traveling with pets.

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Winhall