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House vacation rentals in Winhall

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Popular amenities for Winhall house rentals

House rentals with a pool

Top guest favourite
Home in Wilmington
5 out of 5 average rating, 14 reviews

Spring Hiking Pet Retreat I Game RM l ChimneyHill

LynnRating, 5 stars2 months ago
Shannon’s place was perfect for our Christmas visit with our son. Clean, spacious, great location, fully stocked, and made the perfect place to host our son and his Copper Mountain colleagues for Christmas!
Top guest favourite
Home in Cambridge
4.97 out of 5 average rating, 39 reviews

Country hideaway

GwenRating, 5 stars8 months ago
Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!
Guest favourite
Home in Salem
4.98 out of 5 average rating, 191 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars2 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!
Superhost
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars2 months ago
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.
Guest favourite
Home in Jamaica
4.96 out of 5 average rating, 25 reviews

Ski and tennis house by Stratton Ski Resort.

BillyRating, 5 stars2 months ago
We spent our winter break at Adam's condo. This condo experience had all the important Cs: Clean Condo - it was very clean upon arrival. Convenient Condo - the Stratton shuttle stops right outside the door. Communicative Condo Owner - any questions we had were answered in a timely manner. Cost effective Condo - great value Okay I went overboard with the Cs but honestly it was such a great experience. Adam is great host and the condo worked out perfect for us! Hopefully we get a chance to stay here again!
Superhost
Home in Wilmington
4.79 out of 5 average rating, 56 reviews

Chimney Hill Home w/ New Hot Tub & Amenity Center!

CourtneyRating, 5 stars2 weeks ago
Stayed here as three couples with two dogs and had so much fun. We never left the home because it was so relaxing and enough to do right at the air bnb. Whether we were having a fire, going in the hot tub, playing pool, or making dinners together in the huge kitchen! We will definitely be back!
Guest favourite
Home in Williamstown
4.89 out of 5 average rating, 217 reviews

Hollywood Bungalow in the Berkshires #C0191633410

JohnRating, 5 stars2 months ago
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.
Guest favourite
Home in Granville
4.94 out of 5 average rating, 103 reviews

Historic 1850’s Renovated Farmhouse w/ Pool!

NicoleRating, 5 stars6 months ago
Beautiful home. Pictures don’t do this location justice. Booked for our daughters wedding being held close by for relatives traveling and ourselves to be close to wedding. Would highly recommend for anyone looking in that area. They have thought of everything you could possibly need. We were out at events more than at the home and I honestly with we had done another day to enjoy some down time in the beautiful home. Owners and local property manager were wonderful at communicating and making sure everything was cared for (we had no concerns, but having contacts if there were any)

Weekly house rentals

Guest favourite
Home in Granville
4.85 out of 5 average rating, 188 reviews

Home by the Mettowee River- Simply the best!

RichardRating, 5 stars2 weeks ago
This is my third time staying at Virginia’s house. She is very responsive, checking in via a message to see if everything is going well. It’s an easy walk to the shops and restaurants in the center of the village. I plan to be back again next year.
Superhost
Home in Londonderry
4.94 out of 5 average rating, 174 reviews

Clean, Captivating VT Farmhouse near Stratton!

JamesRating, 5 stars2 months ago
Great house, amazing location near Stratton, and Matthew was just great. He was super communicative, and went above and beyond to make sure we were happy with our stay. We'd love to return again.
Guest favourite
Home in Mount Tabor
4.92 out of 5 average rating, 183 reviews

Spring/Summer Fun Treasures Waiting

JustinRating, 5 stars2 months ago
Great place. Was a bit further from Stratton but close to Manchester and Rutland for food options. It is check in with the hosts - clearly in the instructions - which I overlooked upon booking. The place was just as described and the event brought over blueberry muffins which was a nice touch.
Superhost
Home in North Adams
5 out of 5 average rating, 3 reviews

Charming 6 BR home 8 min walk to MassMoca

StaceyRating, 5 stars7 months ago
Nancy was a great host. She was responsive and proactive providing us instructions for accessing the property. The house had lots of space for our group of 9 and it was nice to have a full kitchen to cook in while we stayed. The walk to MOCA was around 15 minutes with our group, which included five kids. It was nice being so close to town. We hope to be back again!
Top guest favourite
Home in West Brattleboro
4.88 out of 5 average rating, 152 reviews

Cozy Home for 2-5 People in Vermont

TheresaRating, 5 stars1 month ago
Clean and comfortable. Great host who goes above and beyond to make his guests feel comfortable and at home. The beds were comfortable and the bathrooms clean. This place has everything that I look for in an AirBnB stay. We hosted a get together for a dozen family members who live in the area. They were the reason for our trip. People gathered in small groups in the kitchen, living room, dining room and TV room. Plenty of room. It was like having company in my own home.
Guest favourite
Home in Wilmington
4.9 out of 5 average rating, 220 reviews

Wilmington A-Frame- Cozy and Convenient

AveryRating, 5 stars1 month ago
This spot is absolutely perfect to be on a quite spot to enjoy nature but still right within walking distance of the center of Wilmington. The cabin itself is beautifully appointed, gorgeous, and super comfortable. Due to rain we ended up spending most of our time inside relaxing and watching movies, and have zero regrets about it. The host was also extremely friendly, helpful and responsive. I'll definitely be coming back again and recommend this for a Wilmington get away weekend!
Top guest favourite
Home in West Brattleboro
4.93 out of 5 average rating, 117 reviews

Modern Spacious Home with Mountain Views

JoannaRating, 5 stars1 month ago
My family of four loved Christine’s place! She is so thoughtful, leaving yummy snacks plus necessities as well. She’s a great baker and provided us with some yummy treats! The beds were super comfy and cozy, bathrooms were clean and well-equipped and we loved being both close to downtown but also could go hiking out the back door. We feel so grateful to have had such a lovely and relaxing place to stay. Thank you, Christine! ❤️
Top guest favourite
Home in Dover
4.88 out of 5 average rating, 251 reviews

Mt Snow retreat, ski & summer

TimothyRating, 5 stars1 month ago
Wonderful stay in Vermont! Very spacious home with an amazing dining room and theater room in the basement ! Location was perfect for a visit to mt snow, just a few minutes away, and theater room home was cozy, 2 fireplaces , and wonderful! Recommend!!

Private house rentals

Superhost
Home in Manchester
4.87 out of 5 average rating, 23 reviews

Charming Vacation Home in Manchester Center

JakeRating, 5 stars14 months ago
Steal of a deal for this place. Perfect for any couple or family looking to do a vermont ski vacation. Has all the amenities you need, it’s super spacious, it’s right by town, and it’s a short drive to stratton or bromley. Easy 5 stars.
Superhost
Home in Ludlow
5 out of 5 average rating, 18 reviews

2 Units, 1 Home | Perfect for Multiple Families

QiningRating, 5 stars1 month ago
The overall experience is good. Just a reminder: the 1st and 2nd floors use separate doors and are not internally connected. However, the location is very close to Okemo and Killington, and the interior decoration is quite good for the price.
Top guest favourite
Home in Brattleboro
4.94 out of 5 average rating, 121 reviews

Spacious Brattleboro home on river, walk to town

DebbieRating, 5 stars2 months ago
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.
Top guest favourite
Home in Williamstown
5 out of 5 average rating, 13 reviews

Beautiful, cozy house for rent

SteveRating, 5 stars5 months ago
Lovey home and very convenient location in Willamstown. Would highly recommend.
Guest favourite
Home in Dover
4.93 out of 5 average rating, 91 reviews

New Hot Tub! Gas Fireplace! 2 min to Mt Snow

Stacie LynnRating, 5 stars1 month ago
We loved staying in your home. It was close to Mount Snow where we went skiing and we especially loved the fireplace and hot tub. The kitchen was so big and had everything we needed. Thanks so much for leaving the binder of instructions because it is important for us to treat your home like our own home and we want to do things right. We will be back next year. Tom and Stacie
Superhost
Home in Jamaica
4.94 out of 5 average rating, 173 reviews

Cozy Riverfront Home in beautiful Jamaica

CaseyRating, 5 stars2 months ago
Great place. Very isolated and a beautiful location but still has all the creature comforts. The deck, view, and space are amazing. Fast WiFi, 2 bathrooms, and a dishwasher with garbage disposal are really cool in a rustic location like this. The wood fires hot tub was obviously the star of the show. Clear instructions and good communication for everything. The gas grill and gas fire pit were nice. Every thing was comfortable and great. Stress free. Hope to stay here again, thanks for everything.
Guest favourite
Home in Dover
4.89 out of 5 average rating, 71 reviews

Mount Snow House - HotTub/Golfing/Hiking/Skiing

AndyRating, 5 stars2 months ago
Big group of friends and I stayed at Michele's place for a ski-weekend at Mount Snow. House was comfortable and fun with lots of games in the basement and space for us to hang out as a group in the main living area. Hot tub was 🧑‍🍳 perfection. Michele was responsive and helpful via messages.
Guest favourite
Home in Woodford
4.91 out of 5 average rating, 34 reviews

Green Mountains Lake Retreat - Hidden Gem

SarahRating, 5 stars1 month ago
Great little house close to trails. Was perfect for our visit to the Mt Prospect Nordic center. The house was very comfortable and we enjoyed the games and books in our downtime. Would recommend a stay here!

Quick stats about house rentals in Winhall

  • Total rentals

    170 properties

  • Nightly prices starting at

    $152 CAD before taxes and fees

  • Total number of reviews

    3.8K reviews

  • Family-friendly rentals

    160 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

Destinations to explore

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