House holiday rentals in Winhall

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Popular amenities for Winhall house rentals

House rentals with a pool

Guest favourite
Home in Salem
4.98 out of 5 average rating, 192 reviews

Magical Farm Getaway - a must visit!

BriannaRating, 5 stars2 weeks ago
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!
Guest favourite
Home in Colrain
4.9 out of 5 average rating, 129 reviews

The 1770 House

CatherineRating, 5 stars1 month ago
Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!
Superhost
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars4 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.
Top Guest favourite
Home in Wilmington
4.96 out of 5 average rating, 27 reviews

Family/Dog Friendly Mountain Home w/ Amenities

LouisRating, 5 stars1 day ago
Jake’s home is outstanding. The beds are very comfortable. The internet is good, The home has lots of space , a great kitchen with all amenities that we needed. Gas stove etc. The outlay was very comfortable and made for the perfect vacation. I’ve stayed at many homes in the area, Jake’s place is by far the best. We also went to the Clubhouse and used the pool and hot tub which was an added surprise.
Guest favourite
Home in Plainfield
4.89 out of 5 average rating, 139 reviews

Historic Home on 17 acres of land. Go escape!

BrandieRating, 5 stars3 months ago
Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩
Top Guest favourite
Home in Dover
4.98 out of 5 average rating, 52 reviews

Spring Getaway @ Mt Snow! Hike, Bike, Sleeps 8.

JessicaRating, 5 stars3 months ago
We had such a great time staying here! The house was so cozy and clean and was perfect! Felt like being at home and not staying in an Airbnb. Super close to the mountain, especially if you park in carinthia! Loved the guest book that they have in the kitchen, a fun added touch! Robert was extremely responsive to any messages and super accommodating with us and our needs! Absolutely would recommend staying here!!
Guest favourite
Home in Wardsboro
5 out of 5 average rating, 8 reviews

Wander In | Close to Mount Snow & Stratton

KatherineRating, 5 stars3 months ago
This place was a dream for families. We traveled with 4 children and an infant. The house was roomy for the whole crew to hang out and eat together. We loved how clean and organized it was. We enjoyed hours at the pool, which was a huge hit with the littles. VRM was very helpful with any questions that came up. The location was great for skiing at Mt. Snow. We wish we had stayed one more night but our infant became very sick and had to head back a day early. To be honest, the place is more beautiful in person than in the pictures and we feel so lucky to have been able to stay there. Big plus to have laundry on site. Kitchen has everything you need to cook all your meals.
Guest favourite
Home in Granville
4.94 out of 5 average rating, 105 reviews

Historic 1850’s Renovated Farmhouse w/ Pool!

KimberlyRating, 5 stars3 weeks ago
9 adults and 3 children all met up for a family weekend! We came from NY, NH and Maine! The house was perfect! Plenty of room to gather or separate! Even tho it was a chilly rainy weekend the kids managed to get in plenty of pool time! Tanya was very responsive and Melvin was the greatest! Our first morning he came right over to fix a slow drain. Highly recommend!! Kim and family

Weekly house rentals

Top Guest favourite
Home in Argyle
5 out of 5 average rating, 18 reviews

Lakefront gem

RebeccaRating, 5 stars1 month ago
Our stay at the lake was truly amazing! The house was impeccably clean and well-maintained, and the location was perfect for enjoying the lake. Lisa was incredibly responsive and helpful throughout our stay. Highly recommended!
Top Guest favourite
Home in Winhall
5 out of 5 average rating, 57 reviews

Idlewoods

JasonRating, 5 stars3 weeks ago
We had a wonderful getaway here. The house and location were great, and the hosts were very responsive!
Guest favourite
Home in Jamaica
4.92 out of 5 average rating, 99 reviews

The Post Haus: one-of-a-kind modern VT experience

ChadRating, 5 stars1 month ago
Stayed at the Post Haus twice now. Loved it both times. The property and private location is perfect for our rescue dog and is beautiful with the cool river water rapids and unique sky watching experience at day and night.
Superhost
Home in Winhall
4.71 out of 5 average rating, 17 reviews

Stratton Shuttle, Hot tub, Sauna, 2 Suites 5 STARS

JavierRating, 5 stars2 months ago
Fantastic stay at Christopher’s place. Great communication, hastle free booking experience.
Top Guest favourite
Home in East Dover
5 out of 5 average rating, 50 reviews

Magical Retreat Cottage - Waterfalls Everywhere

DavidRating, 5 stars4 days ago
Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.
Guest favourite
Home in Winhall
4.96 out of 5 average rating, 53 reviews

VT Charm, Fireplaces, Hot Tub, Stratton Views

MarinaRating, 5 stars2 months ago
The house was great! Spacious with two living rooms and two fireplaces. Just minutes from Stratton mountain. We loved the hot tub and used the grill too. Check-in super easy and we had an issue on the last day and the host was very responsive.
Top Guest favourite
Home in Winhall
5 out of 5 average rating, 13 reviews

The Vermont Hideaway

AndrewRating, 5 stars3 weeks ago
We had a terrific 2-night stay at Anthony's house in Winhall, just over the border from Manchester. The house is just off of Route 30, about a 5-6 minute drive from downtown Manchester. There was plenty of space for our family, with 4 separate bedrooms (2 on the main floor and 2 downstairs). The house is updated, the furniture is tasteful, and everything was very clean. We would recommend this to anyone looking for a nice place to stay for a weekend in the area.
Guest favourite
Home in Dorset
4.9 out of 5 average rating, 51 reviews

Mountain View Getaway

OliviaRating, 5 stars2 weeks ago
We loved our stay at Nicole’s place. It was very peaceful and private- just what we needed! Our dog also felt right at home thanks to her welcoming touches. We would definitely stay there again!

Private house rentals

Guest favourite
Home in Dorset
4.93 out of 5 average rating, 29 reviews

Charming Vermont Retreat

JanetRating, 5 stars7 months ago
I felt fortunate to discover this rental. It was quiet, clean, and comfortable. We had a workshop near by and this provided a get away to rest between sessions. Catherine responded quickly to my questions. Looking forward to visiting again.
Superhost
Home in Sunderland
4.71 out of 5 average rating, 31 reviews

Modern, Serene Farmhouse Retreat

JerricaRating, 5 stars3 months ago
This place was exactly what we needed to escape and unwind. So relaxing, cozy and comfortable.
Top Guest favourite
Home in Winhall
4.96 out of 5 average rating, 24 reviews

Mountain House between Stratton, Bromley, Magic

ChristopherRating, 5 stars3 months ago
This place is a gem! Large space but felt intimate and cozy. The fireplaces are great, the deck looked inviting but we had so much snow, we spent most of our time on the slopes. Amazing art work throughout, well stocked kitchen, and lots of light! Great space.
Guest favourite
Home in Winhall
4.92 out of 5 average rating, 26 reviews

Multi-Level Ski Retreat at Stratton Mountain

LiliaRating, 5 stars4 months ago
We had a wonderful stay Duojia’s residence! Peaceful location, clean, and the Stratton Mountain view was icing on the cake. There is privacy and so much space at this home. Thank you!
Top Guest favourite
Home in Winhall
4.98 out of 5 average rating, 64 reviews

Stratton 35 acres w/Hot Tub, VIP parking pass

GenRating, 5 stars3 months ago
I had the best time staying at Reid’s beautiful house. The grounds were beautiful and I had never stayed in an ABNB with so much room. The house itself was spotless, tons of room to host a group and equipped for cooking. Reid was extremely easy to deal with and made the trip memorable. Location wise it’s ~3min to get to Stratton base and honestly with the VIP parking pass you can be walking into the town from your within 5min of leaving the house. Would definitely stay here again
Top Guest favourite
Home in Manchester
4.95 out of 5 average rating, 57 reviews

Gather and Relax with Friends & Family

MichaelRating, 5 stars4 days ago
Tod’s place was perfect for my weekend in Manchester with my kids. Not your typical ski crash pad you find all around that area. Tod’s place is an actual home with really comfortable beds, modern amenities and in a really nice and quiet neighborhood. But two minutes after you’re leaving, you’re in the heart of Manchester. The best of all worlds I booked last minute and Tod confirmed quickly. He was incredibly responsive and everything couldn’t have been easier. I’m in Manchester often and would not hesitate to book this house again.
Superhost
Home in Dover
4.91 out of 5 average rating, 82 reviews

FULLY renovated 1 bed/1 bath ski in-out condo!

AnastasiaRating, 5 stars2 months ago
My husband and I spent a long last winter weekend here. The condo was perfect for ski on/off and we enjoyed a day on the mountain. Though the weather wasn’t great the whole time, Brittany & Jen were quick to send recommendations for things to do, trails to hike and their favorite restaurants. So close to lots of great spots in this little mountain town. We would absolutely stay here again
Guest favourite
Home in Winhall
4.85 out of 5 average rating, 41 reviews

Stratton Mountain Ski Chalet

MarkRating, 5 stars4 months ago
Debbie’s home was warm and cozy; perfect for two families (including 3 teens and 2 younger kids) and so close (7 minutes including holiday weekend traffic) to Stratton! We’ll be back!

Quick stats about house rentals in Winhall

  • Total rentals

    170 properties

  • Nightly prices starting at

    $182 NZD 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