House holiday rentals in Woodstock

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Popular amenities for Woodstock house rentals

House rentals with a pool

Guest favourite
Home in Killington
4.91 out of 5 average rating, 212 reviews

Luxury Condo Tucked in the Heart of Killington

KennethRating, 5 stars1 week ago
Very nice place easy access to routes 4 and 100 with plenty of things to do
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!
Top Guest favourite
Home in Mendon
4.89 out of 5 average rating, 247 reviews

Ranch at Mendon Mt Orchards

RobinRating, 5 stars1 month ago
We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!
Superhost
Home in Woodstock
4.82 out of 5 average rating, 382 reviews

White Mountains Ski and Golf Resort Home

ArjunRating, 5 stars4 weeks ago
Great spot! Clean. Bigger than you think. Easy to access just get off the highway!
Superhost
Home in Warren
4.82 out of 5 average rating, 117 reviews

Charming Sugarbush Standalone Condo

PerryRating, 5 stars3 months ago
Great location and lots of space. We were able to ski in/out (look for "Cliff's Road" sign when skiing back) fairly easily, which was nice. Would definitely stay here again. Thanks!
Guest favourite
Home in Woodstock
4.97 out of 5 average rating, 59 reviews

Dana Road House Sunlit VT Country Home w/HotTub

EstherRating, 5 stars6 months ago
Kat’s house on Dana road was the perfect place for our vacation to Vermont. Our family appreciated the clear instructions, helpful hints, and well thought out amenities. We really liked the Whisper Hill products in the bathrooms and made sure we went to the store in Quechee to buy some of the lotion before we left. We have stayed at a lot of AirBnB’s, but the house on Dana road was the most well equipped out of all of our stays!
Guest favourite
Home in Hartford
4.95 out of 5 average rating, 19 reviews

Farmhouse, Fireplace & Office | Wheelock Hideaway

HeidiRating, 5 stars8 months ago
Very quiet and cozy. Comfortable beds. Lots of room for everyone.
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!! 🤩

Weekly house rentals

Guest favourite
Home in Hartland
4.92 out of 5 average rating, 90 reviews

19th Century Bohemian Barn House

ChloeRating, 5 stars8 months ago
We loved our stay at Stacy’s pretty little cottage. It was really spacious. We liked the creativity and quirkiness of the space and we had everything we needed for a family of four. Woodstock and Quechee are nearby and we enjoyed the fall foliage, delicious local food, apple orchards and the amazing local pies. We would definitely stay there again.
Guest favourite
Home in Bridgewater
4.94 out of 5 average rating, 18 reviews

Quaint Cottage

DaliaRating, 5 stars3 months ago
David was very friendly and responsive. We enjoyed the location and the peaceful atmosphere. I was with my sister. The stay was a great experience and felt well worth it. Just a note—one bedroom is accessed via a spiral staircase, another by a ladder, and there’s a sleeper couch in the living room. Would definitely recommend!
Guest favourite
Home in Woodstock
5 out of 5 average rating, 16 reviews

Fabulous Log Home in the Woods

KathyRating, 5 stars1 month ago
The log cabin is very comfortable with great flow. Loved the sunroom and upstairs den. Heated floors in bathrooms and sunroom were great touches. Not conventional decor: maximally furnished with an interesting blend of western, contemporary abstract art and figurative paintings and knick- knacks. We thought it fun and loved our stay.
Superhost
Home in Quechee
4.82 out of 5 average rating, 146 reviews

Shelly's Place

NancyRating, 5 stars2 months ago
The location was perfect for our appointments at Dartmouth! We enjoyed the area..it was so convenient. Access to a gas station, Dunkin Donuts, Jakes Market, Skinny Pancake and Marshland Farms Inn(where we had a lovely dinner) within a couple of minutes from the home, yet the home was very quiet and private. We are hoping the weather is nicer our next trip so we can visit VINS, Queechee George and the Antique Mall. Thanks Michelle!
Top Guest favourite
Home in Windsor
4.99 out of 5 average rating, 94 reviews

Stylish Ascutney Cabin •View •Chef’s Kitchen •Pets

AmandaRating, 5 stars1 week ago
We had a great stay! The house was well-appointed and comfortable. We especially loved the covered porch and beautiful view. It was a great home base for exploring the area, including several nearby hiking trails, Woodstock and Quechee (about a half hour away), and Brattleboro (less than an hour away). Ab was a fantastic host. He was proactive with communication and even checked in with us to make sure we had power after some strong thunderstorms that had moved through the area.
Guest favourite
Home in Bridgewater
4.98 out of 5 average rating, 57 reviews

Secluded/Hot Tub/views! Minutes to Everything!

AndreaRating, 5 stars1 month ago
The space was just as described. The view of the mountains is beautiful, and the house sits far enough above the road that there's no sounds of traffic. It felt secluded and peaceful, with all the amenities one would need.
Top Guest favourite
Home in Hartland
5 out of 5 average rating, 29 reviews

The Brook House

KellyRating, 5 stars2 weeks ago
I can't say enough great things about Jeff and this beautiful rental. The house is gorgeous with every amenity we could have wished for. The property was breathtaking with manicured gardens, fire pit area and the roaring brook right outside the windows. The water was pretty high when we were there due to all the rain, but it made for the most peaceful background sound. Linens were high end, beds were comfortable, the house was spotless, Jeff was super responsive and accommodating to our large group. I could go on. Would love to rent again in the future! Thank you Jeff!
Superhost
Home in Woodstock
4.95 out of 5 average rating, 22 reviews

The Westerdale - A Quiet Woodstock Retreat

KeriRating, 5 stars5 months ago
Ashley was incredibly helpful, kind, and responsive. Highly recommend!

Private house rentals

Top Guest favourite
Home in Barnard
4.99 out of 5 average rating, 95 reviews

BEST Views! Close to Silver Lake + Woodstock VT

BetsyRating, 5 stars3 weeks ago
We came here with our infant and had the perfect little trip. Amazing house — just as pictured, beautiful view, super clean, amenities, sauna. And awesome location— the house is very quiet and rural, but it’s close to a lot of spots— we went to breakfast at Barnard General Store (best pancakes of my life x100), went into Woodstock to walk around and eat, went to Longtrail Brewery for Friday night trivia, quechee gorge for a small but pretty hike, Worthy Burger for food and cocktails, and silver lake syrups to learn about and buy maple syrups (including taste tests) … lots to do. We had bad weather all weekend; if it had been good weather, it would’ve been even better with hiking and stargazing and outdoor fire. I don’t like to go to Airbnbs twice, but this place is high on my list to visit again- either in the summer or winter. Jenny is a very responsive and helpful host. Overall one of my best Airbnb experiences.
Top Guest favourite
Home in South Pomfret
5 out of 5 average rating, 47 reviews

Cheerful, Restored 1940s Cape- 5 mins to Woodstock

EmilyRating, 5 stars2 months ago
We loved our stay at Maura's place! We had a girls weekend and the space comfortably fit all 7 of us. We felt right at home, and the location was amazing! Beautiful views of the S6 ski mountain, convenient to the general store at the end of the street, and so convenient to beautiful Woodstock for restaurants, shopping, hikes, etc. The beds were comfortable and we felt like the hosts went above and beyond with communication and recommendations. Would definitely stay again!
Guest favourite
Home in South Woodstock
4.9 out of 5 average rating, 31 reviews

Grange Hall, South Woodstock Historic Home

CiriRating, 5 stars1 month ago
We love our stay! The location was perfect, and the house was very comfortable. The kitchen and bathroom look recently updated, and there is a beautiful stone patio by the river. We hope to be back!
Top Guest favourite
Home in Norwich
5 out of 5 average rating, 70 reviews

Relaxing Countryside Oasis!

MegRating, 5 stars2 weeks ago
We had a wonderful stay! We would absolutely recommend staying here. The house worked well for myself, husband and 4 year old son. There were even a few toys he was able to play with, in addition to a large lawn and a stream near by! There are also very thoughtful touches with amenities to make traveling and staying somewhere more convenient and comfortable.
Superhost
Home in Woodstock
4.82 out of 5 average rating, 85 reviews

Riverside Home Woodstock VT

Anne MarieRating, 5 stars2 weeks ago
This house was wonderful. Had so many thoughtful amenities, especially for families with children. Lots of kids toys, books, games. There was plenty of sleeping space and lounging space. Especially loved the big kitchen table. We really appreciated that the kitchen was stocked with some helpful pantry items and also had plenty of cookware. It made cooking for 3 large families easy and enjoyable. We will definitely be back. thank you!
Superhost
Home in Hartland
4.86 out of 5 average rating, 72 reviews

Cozy 1 bedroom home with private hot tub

MadysonRating, 5 stars1 month ago
Great place to relax and unwind with friends! We had an amazing time and the hot tub was a great touch!
Superhost
Home in Plymouth
4.77 out of 5 average rating, 405 reviews

BEST OF LAKE FRONT LIVING, HOT TUB & FIREPIT !!

AveryRating, 5 stars4 days ago
Absolutely loved staying here for our anniversary. It had everything we needed to unwind and relax. The views were beautiful from just about every spot on the property and every detail was included to make the stay feel more at home.
Guest favourite
Home in West Windsor
4.97 out of 5 average rating, 95 reviews

3BR Country Retreat | Private and Peaceful

MarchantRating, 5 stars4 days ago
It’s a beautiful house in a private area. Great outdoor seating with tables, a sitting area and a fire pit area. Super clean and lots of space!

Quick stats about house rentals in Woodstock

  • Total rentals

    70 properties

  • Nightly prices starting at

    $201 NZD before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Woodstock
  6. House rentals