House vacation rentals in Pittsfield

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages
0 of 0 items showing
1 of 12 pages

Popular amenities for Pittsfield 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
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!
Guest favorite
A spacious outdoor area features a refreshing pool surrounded by lush greenery and wildflowers. Comfortable seating is arranged nearby, providing an inviting gathering space. The backdrop consists of tall trees and distant mountains, creating a serene atmosphere for relaxation and outdoor activities.
Home in Waitsfield
5 out of 5 average rating, 10 reviews

Private 5BR Mt. view, pool, new hot tub

EliasRating, 5 stars2 months ago
This house was incredible. Open concept first floor to gather for making dinner and eating around the table. Incredible views of the Mad River Valley, a hot tub, and room downstairs to hang out. Highly recommend for a weekend of skiing.
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, 188 reviews

Home by the Mettowee River- Simply the best!

RichardRating, 5 stars6 days 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.
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.
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 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.
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
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.
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.
Superhost
The charming cabin is set amidst vibrant fall foliage, featuring a gray exterior and a metal roof. A winding gravel driveway leads to the entrance, with colorful bushes adding natural beauty to the landscape. Surrounding trees provide a serene backdrop.
Home in Ludlow
4.67 out of 5 average rating, 102 reviews

Pete's Place Cabin Okemo/Killington (whole house)

BrianRating, 5 stars3 months ago
Pete's Place was fantastic. Our family of 6 (with 4 boys) really enjoyed it. Great place to get away from the crowds, yet super convenient location to OKEMO (particularly the Gore Area) and very short drive into town for groceries/restaurants.
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!
Guest favorite
The house is nestled among trees, reflecting a modern design with an asymmetrical roof. Snow covers the ground, creating a serene winter landscape. A small porch with a railing is visible, alongside large windows that hint at the interior's open layout.
Home in Waitsfield
4.91 out of 5 average rating, 149 reviews

Sweet Blue Mint Ski House

TommyRating, 5 stars3 weeks ago
This is our second stay here. The house is roomy and clean. We even had a visit from the neighborhood bear!!! Location is perfect and private. I highly recommend.
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 stars4 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
An open living area features a cozy gray sofa facing a stone-accented wall with a mounted television and electric fireplace. Large windows allow natural light to fill the space, while a modern chandelier adds brightness. A dining table is situated nearby, enhancing functionality.
Home in Plymouth
5 out of 5 average rating, 9 reviews

Snowledge II by Okemo/Killington

GiannaRating, 5 stars2 months ago
Lovely stay!!! She’s not kidding about the AWD or 4WD. One of our cars couldn’t make it up the driveway after it snowed. Beautiful place with everything you could possibly need. The coffee machine really saved us. Thank you and would definitely recommend!
Top guest favorite
A serene outdoor space features a wooden gazebo surrounded by lush greenery. Comfortable seating is arranged inside, providing a gathering area to enjoy sunset views. The landscape includes rolling hills in the background, with a colorful sky transitioning into twilight.
Home in Reading
4.99 out of 5 average rating, 73 reviews

Secluded home on a hillside Reading, VT

EdwardRating, 5 stars6 months ago
This place was amazing, it was so beautiful we decided to do our wedding ceremony on the grounds. Everything was just as the pictures and description says! Would highly recommend this home to anyone who is traveling to this area. Host Pamala and her husband were very respectful and responsive. Great home…

Quick stats about house rentals in Pittsfield

  • Total rentals

    40 properties

  • Nightly prices starting at

    $170 before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Rutland County
  5. Pittsfield
  6. House rentals