House vacation rentals in Stockbridge

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Popular amenities for Stockbridge house rentals

House rentals with a pool

Guest favorite
Aerial view of a snow-covered landscape, showcasing rolling hills and a winding road. The scene includes a mix of bare trees and patches of evergreen, while the distant mountains hint at recreational opportunities. A clear sky and soft sunlight enhance the serene atmosphere.
Home in Killington
4.91 out of 5 average rating, 202 reviews

Luxury Condo Tucked in the Heart of Killington

AshleyRating, 5 stars2 weeks ago
Comfortable and convenient location. Everything we needed was in the kitchen. We had most of our meals in and took advantage of the kitchen. The sleeping accommodations were very comfortable. It is only a short drive to Killington, where my family skied. We would definitely stay there again.
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 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!
Guest favorite
Home in Granville
4.96 out of 5 average rating, 141 reviews

Epic Views of the Green Mountains

StephenRating, 5 stars3 weeks ago
Great place to take your family if you like to escape from humanity! Very remote setting and plenty of places to hike. The house is as described and the kitchen if fully stocked to make full dinners. My daughters, our German Shepard and I had a wonderful time. Suggestions - bring groceries as Granville is in the middle of nowhere. Closest store is in Rochester, 12 miles South. William was very commun icative and the value for the money was phenominal. Hope I can return next year!
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, 245 reviews

Ranch at Mendon Mt Orchards

StephanieRating, 5 stars1 week ago
Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!
Top guest favorite
Home in Waitsfield
5 out of 5 average rating, 31 reviews

Winter Wonderful Waitsfield Spacious VT Home w/Spa

SeanRating, 5 stars6 months ago
Our stay in Sara and Mikes home in Waitsfield was incredible! Upon arrival into the mad river valley, the surrounding views were instantly beautiful and calming. The moment we stepped in the house we honestly felt right at home. The layout of the house is so calming and tasteful. Everything is perfectly organized, down to the labeling for all of the dishes and cookware so you’ll never have trouble finding what you need! Waking up and heading by downstairs for a workout in the home gym, followed by a dip in the hot tub on the secluded back deck was an insanely relaxing way to start the day. The custom built bed frames/furniture and the overall craftsmanship of the space added a comforting artistic value to the stay. Don’t get me started on the screen porch! This house is full of amenities and I’ve honestly never felt more at home at an air b&b stay. Nice quiet respectful neighborhood in an amazing community, would recommend this spot to anyone and we hope to return in the future!
Top guest favorite
An aerial view captures a spacious, one-story home surrounded by expansive green lawns and wooded areas. The property features a detached garage and a shed, with ample outdoor space visible for recreational activities.
Home in Barre
4.94 out of 5 average rating, 67 reviews

Charming Barre Getaway

AaronRating, 5 stars1 month ago
The best stay around! Barre is a great little walkable town with shops and restaurants to explore. It’s only a short drive to local ski / snowboarding mountains as well as some hiking. The house was clean, spacious and very nicely decorated. The kitchen had everything we needed that made it feel like we were cooking right at home, which we loved. Karen and Courtney were responsive and very helpful!
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 Warren
4.82 out of 5 average rating, 117 reviews

Charming Sugarbush Standalone Condo

PerryRating, 5 stars1 month 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
A spacious green lawn surrounds a rustic farmhouse, showcasing a red wooden structure with a metal roof. Nearby, an outbuilding and a covered area with picnic tables are visible. Trees and gentle hills create a serene backdrop, illustrating a peaceful rural setting.
Home in Hartland
5 out of 5 average rating, 10 reviews

Private Farmhouse with in ground pool!

ChrisRating, 5 stars7 months ago
My family and I truly enjoyed our time spent at the farmhouse. Everything was as expected from the listing. The pictures do not do justice for the property. It's beautiful and well maintained. The pool was nice, warm, and clean. There are yard games readily available and a nice fire pit area. Brin and Maria are super responsive and left very detailed instructions on the property for you. Everything you need is there minus food, which is a 12-minute drive towards a few different grocery stores. The hill is so fun to roll down, too! Thank you so much!

Weekly house rentals

Guest favorite
A modern kitchen area features a large island with a deep sink and abundant counter space. Natural light floods in through large windows, illuminating the dining table and lounge. A wood-burning stove adds warmth to the open-plan space, creating a seamless connection with nature.
Home in Lincoln
4.98 out of 5 average rating, 205 reviews

Modern Home in Lincoln Sauna / Pond / Ev Chg / Pvt

CatherineRating, 5 stars1 month ago
Bjorn’s home is pristine and could not be nestled in a more beautiful place. He was very responsive and the house is well supplied with everything you could need. Highly recommend and look forward to staying here again!!
Guest favorite
The living room showcases a spacious layout with two blue sofas and a patterned area rug. A wooden coffee table is centrally placed, displaying a selection of magazines. Natural light flows in through large windows, complemented by soft lighting from a nearby lamp.
Home in Granville
4.85 out of 5 average rating, 187 reviews

Home by the Mettowee River- Simply the best!

LoganRating, 5 stars1 month ago
The place was great! Adorable home in a great location. Restaurant's, grocery stores, and activities were all within 5 min from the home, yet it was still on a nice quiet street. Had all the amenities listed which made it super easy to cook meals. Directions for check in and check out were very clear and easy to follow. Virginia and Dan were amazing hosts, easy to communicate with, hospitable, and very attentive. Definitely a place I would highly recommend!
Guest favorite
A charming red barn is set against a backdrop of vibrant fall foliage in various shades of orange and green. A stone pathway leads from the house to the barn, which is framed by lush grass and trees.
Home in Bristol
4.88 out of 5 average rating, 155 reviews

Large New England Home w/ Gorgeous Mountain Views

ChristopherRating, 5 stars2 months ago
This is a great house to stay in. There's a lot of space, places to sleep, sit and relax, eat, watch tv, play games, work, read, cook. Plenty of hot water.. Very private, although in a neighborhood. Nice back yard area when not covered in snow, looking up at the mountains behind. Sheri is top notch. Easy to reach, super friendly and helpful, easy going. We came at the tail end of a snow storm, but the driveway was cleared enough to get our car in and then Sheri worked with us to make sure everything was cleared before we had to go out the next day. Easy walk into the cute town of Bristol. Handful of nice shops (books, games, art, crafts, gifts, toys) and restaurants: Wokky's--ok Chinese/great staff; Minifactory--out of sight coffee/biscuits/sandwiches/fresh ingredients/lot of gluten free; Cubber's--locals' joint/excellent pizza/sandwiches; Farmhouse Chocolates--superb fresh organic truffles, bars, caramels/chocolatier is wonderful. Easy drive to Mad River Glen, Sugarbush for skiing.
Superhost
The charming exterior of a farmhouse is surrounded by lush greenery, featuring a pale blue façade and a welcoming pink door. Dense foliage and colorful flowering plants enhance the inviting approach to the home, set against a peaceful landscape.
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.
Top guest favorite
A modern two-story house is set on a spacious lawn accompanied by trees. A brick chimney rises against a backdrop of a blue sky with scattered clouds. A stone pathway leads to a welcoming front porch, which is adorned with lanterns and surrounded by well-kept shrubs.
Home in Sunapee
4.97 out of 5 average rating, 114 reviews

Sunapee Four Season Getaway with a Mountain View

SamanthaRating, 5 stars1 month ago
We had an amazing family ski weekend at this house! With four young children, finding a place that accommodates everyone can be challenging, but this house was perfect. It had two cribs, which was a huge bonus for us. The open floor plan made it easy to keep an eye on the kids while still enjoying time together as a family. The hot tub was a great way to relax after a day on the slopes, and there was plenty of space for our entire group to spread out and feel comfortable. The location was also fantastic—just a short drive to Mount Sunapee, making it so easy to hit the slopes. We couldn't have asked for a better place for our weekend getaway!
Superhost
The exterior of the home is shown, featuring a two-story structure with a large covered porch and colorful flower pots. Surrounding trees exhibit autumn foliage, while manicured grass adds to the inviting atmosphere. A clear blue sky complements the scene.
Home in Moretown
4.92 out of 5 average rating, 139 reviews

South Hill Lodge- 5 BR Post & Beam Home

JenniferRating, 5 stars2 months ago
Beautiful home, as described. Nice personal touches with towels and mini shampoo/conditioner. Kitchen is large and has most every appliance you would want. Caretaker does come in twice per day but is friendly and unobtrusive. You do need AWD/4WD to access the house.
Guest favorite
A shaded outdoor area features a tree with two swings, one being a macrame-style chair with striped fabric. The wooden exterior of a neighboring building and a picnic table can be seen in the background, enhancing the tranquil and inviting atmosphere of the space.
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
The exterior of a charming farmhouse is shown, featuring a large front porch and classic architectural details. Lush greenery surrounds the property, while a driveway leads to a carport. An American flag flutters proudly in front of the house under a clear blue sky.
Home in Cavendish
4.8 out of 5 average rating, 71 reviews

OKEMO MT HOUSE - OKEMO-LUDLOW-JACKSON GORE

RobertRating, 5 stars2 months ago
House fit our need was a good location for skiing at Okemo

Private house rentals

Superhost
The exterior of the house is shown, featuring a two-story structure with a metal roof and large windows. A spacious wooden deck extends from the main entrance, surrounded by bare trees and a lightly snow-covered yard. Natural scenery hints at a tranquil setting.
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.
Superhost
The home features a modern design with dark siding and multiple large windows. A spacious, sunlit deck extends from the house, adorned with lounge chairs. Surrounding greenery and landscaped areas provide a natural contrast to the structure.
Home in Waitsfield
5 out of 5 average rating, 3 reviews

FULL HOUSE w/HOT TUB - Waitsfield Common

LauraRating, 5 stars6 months ago
This home is beautiful, spacious and is surrounded by nature. The backyard had a huge deck with a tree lined backyard and you can hardly see the next neighbour. There are rolling hills and cows in the next pasture. So serene. The house has lots of room in the main area for our family, it never felt crowded. The kitchen looks better then the pictures, with a huge island and the entire house is fully stocked. You can tell this is not just a rental as it had more then we expected to live comfortably. She was also kind enough to bring us some baby items. The location is great as wherever you turn it's beautiful but also within driving distance to Stowe. The local towns are really cute too. Our family really enjoyed our time here.
Guest favorite
A charming wooden house is situated amidst a lush green landscape, surrounded by trees. The home features a distinctive roofline and large windows that invite natural light. A gravel path leads to the house, with boulders and grass adding to the scenic outdoor environment.
Home in Killington
4.94 out of 5 average rating, 117 reviews

Cozy Private House on Killington Mtn - Hottub

MeganRating, 5 stars1 month ago
This airbnb was even better than we expected! It is just minutes away from all the Killington lodges and the restaurants/bars in town. The house was extremely clean, easy to find, and perfect for a group of skiers. I highly recommend it for anyone looking for a beautiful, easy place to stay at Killington. Would love to stay here again next time we visit! Highly recommend.
Top guest favorite
Home in Ludlow
5 out of 5 average rating, 42 reviews

New Home on 23 Acres-Views of Okemo w/ Hot Tub

JenniferRating, 5 stars1 month ago
This home is absolutely beautiful, with stunning views that make for a perfect Vermont getaway. The house is well-equipped with everything you need for a comfortable and relaxing stay. The location is fantastic—close to local attractions yet peaceful and private. Whether you’re looking for a cozy weekend retreat or an adventure in nature, this spot has it all. Highly recommend!
Guest favorite
The unique architectural design of the house is set against a backdrop of snow-covered trees. Sunlight illuminates the structure under a clear blue sky, with snow blanketing the ground, creating a serene winter landscape.
Home in Warren
4.83 out of 5 average rating, 52 reviews

4 story 3BR 2BA sunlit house w/ gorgeous mtn views

TaraRating, 5 stars3 months ago
Very unique house with incredible views. Great location for getting outside, and had everything we needed. Was perfect for skiing and we would love to see this place in the summer!
Top guest favorite
The exterior of the post & beam house is shown, surrounded by a snowy landscape. A spacious balcony extends from the upper level, while large windows invite light into the interior. Trees are visible in the background, completing the serene winter setting.
Home in Warren
5 out of 5 average rating, 14 reviews

LaFlame Chalet - 10 mins to Sugarbush

JohnRating, 5 stars3 weeks ago
We had a great stay at this cozy Airbnb. Looks exactly like the pictures and is a perfect size for group of friends or family. We brought a dog and had no issues at all. The hosts were very kind and even helped us with some car troubles after an unexpected snow storm. Would recommend and overall great stay!
Guest favorite
A bright bedroom featuring a spacious bed dressed in a multicolored quilt. Natural light floods in through large windows that offer views of the surrounding forest. A rocking chair is placed beside a small table, and a standing lamp provides additional illumination.
Home in Warren
4.9 out of 5 average rating, 69 reviews

Lovely private house in the mountains

RebeccaRating, 5 stars2 months ago
We had a very nice stay, especially appreciating the proximity to Sugarbush and the responsiveness of the host.

Quick stats about house rentals in Stockbridge

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    980 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

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