House vacation rentals in Woodstock

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Popular amenities for Woodstock house rentals

House rentals with a pool

Guest favorite
The farmhouse features a classic two-story white exterior with green shutters and multiple windows. Snow covers the ground in front, while the entrance is highlighted by a center door flanked by sidelights. A gentle landscape with shrubs is visible on either side.
Home in Salem
4.98 out of 5 average rating, 191 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars3 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!
Top guest favorite
The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.
Home in Mendon
4.89 out of 5 average rating, 247 reviews

Ranch at Mendon Mt Orchards

RobinRating, 5 stars4 weeks 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
An aerial view of the property captures a serene outdoor space featuring a rectangular pool surrounded by lounge chairs. Nearby, tennis courts are visible, set against a backdrop of green lawn and trees, providing an inviting area for leisure activities.
Home in Sugarbush Village
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 favorite
The charming yellow home is set against a backdrop of autumn foliage, showcasing green lawns and a wooden fence. A gazebo is visible nearby, inviting relaxation. The structure features a gabled roof and is oriented towards the scenic landscape.
Home in Woodstock
4.97 out of 5 average rating, 59 reviews

Dana Road House Sunlit VT Country Home w/HotTub

EstherRating, 5 stars5 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 favorite
A fenced outdoor pool area is surrounded by lush greenery and tall trees. The pool is heated and saltwater, reflecting the sunlight. Adjacent to the pool, a small shaded structure provides additional space and amenities.
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!! 🤩
Superhost
The exterior of a newly renovated retreat showcases a wooden structure surrounded by trees. A fire pit is set with several dark chairs arranged in a circular formation. Soft light emanates from the large windows, providing a glimpse into the warm interior spaces.
Home in Bridgewater
4.89 out of 5 average rating, 46 reviews

Luxurious family retreat home in the mountains

DanielleRating, 5 stars10 months ago
Andreas place was gorgeous and looked just like the pictures. The house was clean and organized and the backyard was wonderful to relax in.
Superhost
A wooden dining table is set with plates and glassware, accompanied by upholstered chairs. Above, a modern light fixture with hanging bulbs provides illumination. A cozy living area with a fireplace and a television is seen in the background, enhancing the communal atmosphere.
Home in Hartford
4.88 out of 5 average rating, 16 reviews

Elegance Meets Rustic Charm: Vermont 3-Bed Retreat

JulieRating, 5 stars10 months ago
Our stay was a family group of six adults and my two grandchildren who are ages seven and eight. We decided to spend the week in Queechee with the second weekend being a family wedding. We loved the peace and comfort of a private home and especially enjoyed the backyard deck playing cornhole and barbecuing. Being tucked away up off of Willard Road was worth the very slight inconvenience of an extra five minutes or so drive to get back into Queechee proper. The owners were very responsive to any concerns or questions I had about the property during our stay. The home is spacious and lovely with attractive and comfortable furnishings. The kitchen is open to the main level and very well equipped for cooking all your meals if you choose. our granddaughters enjoyed the games that are stashed away in the front closet Highly recommended!
Guest favorite
A historic farmhouse with a two-story white exterior is surrounded by lush green grass and trees. A large wrap-around porch features rocking chairs, and a side deck has a dining area with umbrellas. The inviting facade is complemented by bright blue skies.
Home in Granville
4.94 out of 5 average rating, 105 reviews

Historic 1850’s Renovated Farmhouse w/ Pool!

KimberlyRating, 5 stars2 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

Guest favorite
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 favorite
The exterior of the log-style home features a covered porch supported by sturdy wooden beams. Lush gardens filled with colorful flowers and greenery line the front, creating a vibrant entrance. The blue metal roof adds a contrasting touch to the rustic design.
Home in Woodstock
5 out of 5 average rating, 16 reviews

Fabulous Log Home in the Woods

KathyRating, 5 stars3 weeks 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.
Guest favorite
A charming cottage is situated among lush greenery, featuring a white exterior and a well-maintained front yard. A gravel driveway leads to the entrance, framed by flowering shrubs and trees providing natural shade. The peaceful setting reflects a tranquil ambiance ideal for a relaxing retreat.
Home in Woodstock
5 out of 5 average rating, 7 reviews

Cozy Cottage by The Green

ChristineRating, 5 stars3 months ago
Amazing location, very cute and cozy! Walking into town for coffee or to window shop was easy, and the house was warm and welcoming. The living room has more seating than shown in the photos, which is fantastic. Woodstock is also just such a fun spot. Though it didn't matter to us at all, it may matter to some that the door to the upstairs bathroom and at least one bedroom didn't fully latch nor lock. 10/10 would stay here again!
Top guest favorite
An open living and dining area presents a light wood floor complemented by white and transparent furnishings. A soft couch is paired with an armchair. A flat-screen TV is mounted on the wall while large windows allow natural light to enhance the space.
Home in Hartford
4.98 out of 5 average rating, 47 reviews

Hartness Haven | Private screen porch

KarenRating, 5 stars1 month ago
We loved Hartness Haven, it is a beautiful home in equally beautiful surroundings. You feel right at home with comfortable furniture and a very well stocked kitchen. The beds are comfortable and the whole house is spotless. We really enjoyed the screened in porch and the fire place in the backyard. It is close to Quechee and Woodstock as well as several hiking trails. I would absolutely recommend Hartness Haven and hope to return soon!
Top guest favorite
Home in Windsor
4.99 out of 5 average rating, 94 reviews

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

AmandaRating, 5 stars4 days 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 favorite
A charming mountain house is shown at dusk, with warm lights glowing from multiple large windows. A hot tub, illuminated in soft blue, sits on a deck surrounded by snow. The area is framed by tall trees and distant mountain views.
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 favorite
Home in Hartland
5 out of 5 average rating, 29 reviews

The Brook House

KellyRating, 5 stars1 week 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
A cozy living area features a leather sofa and two red leather chairs, positioned around a wooden coffee table. Natural light enters through glass doors leading to a grassy outdoor space. A colorful rug and decorative elements create a welcoming ambiance.
Home in Woodstock
4.95 out of 5 average rating, 22 reviews

The Westerdale - A Quiet Woodstock Retreat

KeriRating, 5 stars4 months ago
Ashley was incredibly helpful, kind, and responsive. Highly recommend!

Private house rentals

Top guest favorite
A sunlit living area features a brown leather sectional sofa adorned with decorative pillows. Large glass doors offer views of the surrounding landscape, while modern lighting fixtures illuminate the space. A circular white coffee table is positioned in front, enhancing the open layout.
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 favorite
A welcoming entrance features a wooden deck leading to a door framed by potted plants. Seasonal decorations, including orange and white pumpkins and vibrant mums, enhance the steps. The surrounding area includes gravel and hints of greenery from nearby nature.
Home in Barnard
5 out of 5 average rating, 24 reviews

Sunflower Burrow Cottage

MichaelRating, 5 stars1 week ago
We enjoyed staying at Sunflower Burrow! It had all the things we needed. Highly recommend to anyone visiting the area.
Guest favorite
A historic brick building from 1824 is featured, showcasing a flat metal roof and traditional dark shutters. Surrounding trees display autumn foliage, adding warmth to the scene. A quiet road leads to the home, inviting exploration of the charming neighborhood.
Home in South Woodstock
4.9 out of 5 average rating, 31 reviews

Grange Hall, South Woodstock Historic Home

CiriRating, 5 stars4 weeks 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!
Superhost
The exterior of a rustic red home is presented, featuring a tin roof and an expansive porch. Surrounding greenery includes trees and shrubs, contributing to the natural setting. A clear blue sky provides a bright backdrop to the welcoming structure.
Home in Woodstock
4.82 out of 5 average rating, 84 reviews

Riverside Home Woodstock VT

TomRating, 5 stars4 months ago
Nandini's home is in a good location and is very comfortable for a family. There is a large kitchen table for everyone to sit and play games. Family room is a large U shape for comfortable conversation. Pool table is located next to the kitchen and family room. 4 bedrooms and 3 bathrooms was the perfect size. Killington is nearby and Long Trail brewery and farmers market are right down the road. We had a wonderful time. 5.0/5
Top guest favorite
A charming two-story home is situated among lush greenery, framed by large trees. The front porch features inviting seating and offers a glimpse into bright windows that allow natural light. Surrounding grass enhances the peaceful, rural setting.
Home in Bradford
5 out of 5 average rating, 51 reviews

Ski Sunapee or Pat’s Peak Look To The Mountain

DalbertRating, 5 stars1 month ago
Absolutely incredible experience! From the moment we arrived, it was clear that this place was something special. The property was immaculate—clean, beautifully decorated, and thoughtfully stocked with everything we could possibly need for a comfortable stay. Every detail, from the cozy bedding to the pristine kitchen, was perfection and made our trip unforgettable. Judith went above and beyond in every way, and clearly thought of everything a guest would need to feel right at home. She is also very responsive and easy to communicate with Without question, this property sets the gold standard for all Airbnb rentals. If every Airbnb were like this one, hotel chains would be out of business. We can’t recommend it highly enough and will absolutely be back. Mahalo you for an exceptional stay and A Hui Hou!
Top guest favorite
A dining area is seen through an open doorway, featuring a wooden table surrounded by six chairs. Warm lighting is provided by a chandelier above, while a bowl of flowers centers the table. A patterned rug lies beneath, and cabinetry is visible in the background.
Home in Hartford
4.97 out of 5 average rating, 94 reviews

Charming, Cozy Cape

IsadoraRating, 5 stars1 week ago
A beautiful place with windows in every room to enjoy the stunning surroundings. Easy access, convenient parking, smooth check-in, and everything was clean and well organized. The beds and dining table were thoughtfully prepared, and the host was responsive and flexible — allowing us to drop off our bags early so we could attend a Tuck lecture. The whole experience was excellent. Thank you!
Guest favorite
The exterior of a two-story home is set among vibrant gardens filled with colorful flowers. A neatly maintained lawn extends toward a shaded area featuring rustic seating. Lush trees and greenery complete the serene landscape, providing a peaceful and inviting outdoor atmosphere.
Home in West Windsor
4.97 out of 5 average rating, 94 reviews

3BR Country Retreat | Private and Peaceful

KatyRating, 5 stars2 weeks ago
This home was the perfect base for a Vermont getaway! We stayed as two small families with kids and had plenty of space to relax and enjoy the weekend. The house was spotless, the beds were super comfortable, and the peaceful setting surrounded by nature made it even more special. It was such a treat to come back and unwind here after exploring Woodstock, Quechee, and Hanover, NH. We hit all our favorite spots—Simon Pearce Gallery, Hartland Diner, and the great shops and restaurants in Woodstock. So much fun!
Guest favorite
An open-concept living area showcases a spacious white sofa with black accent pillows, accompanied by two dark chairs. Large windows provide views of the surrounding greenery, while a dining table with seating for eight is positioned near the natural light. Modern light fixtures enhance the ambiance.
Home in Grantham
5 out of 5 average rating, 30 reviews

Eastman Luxury Retreat Dartmouth College /Sunapee

MarthaRating, 5 stars2 weeks ago
I had a fantastic stay! The place was clean, comfortable, and exactly as described. The host was a great communicator and made the whole process easy. Highly recommend

Quick stats about house rentals in Woodstock

  • Total rentals

    70 properties

  • Nightly prices starting at

    ﺩ.ﺇ441 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