House vacation rentals in Middlesex

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Popular amenities for Middlesex 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.
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
A spacious living room is illuminated by large windows overlooking the forest. A leather sofa and armchair are arranged around a patterned area rug. A coffee table and side table with modern lamps complete the cozy seating area. A wood-burning fireplace adds warmth to the setting.
Home in Killington
4.98 out of 5 average rating, 133 reviews

SugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace

JeffreyRating, 5 stars1 month ago
Dan and Holly are wonderful hosts. Excellent condo unit in a quiet, private location yet very close to great skiing, excellent restaurants, and live music. Condo was spacious, clean, and well kept. Dan and Holly obviously really care about their guests. Highly recommended.
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!
Superhost
A charming yellow house is surrounded by lush greenery and vibrant flowers. Well-maintained gardens feature an array of colorful blooms, with a decorative trellis enhancing the welcoming entrance. Mature trees provide a natural backdrop, contributing to a serene atmosphere.
Home in Stowe
5 out of 5 average rating, 3 reviews

Cool Pool, a Private Oasis

MeganRating, 5 stars9 months ago
Lovely house and beautiful lot! Spent lots of time playing in the yard, swimming in the pool and exploring all the things that Stowe has to offer. We'll be back!
Guest favorite
The lodge's exterior is showcased under a serene blue twilight, surrounded by snow-covered terrain. The circular structure features large windows that warmly illuminate the interior. Snow-covered mountains rise majestically in the background, with ski trails visible on the slopes.
Home in Stowe
4.94 out of 5 average rating, 190 reviews

Cozy Studio Spruce Peak Lodge Ski in Ski Out | 319

MartinaRating, 5 stars5 months ago
Had another great stay at the lodge! Stephanie was very responsive. Will definitely book with her again!

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
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 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 spacious bed is dressed in a quilt featuring soft pastel colors and patterns. Two pillows rest at the head, with a patterned throw blanket draped across the bed. In the background, a partially visible bathroom is seen through an open doorway.
Home in Warren
4.92 out of 5 average rating, 206 reviews

Beautiful guesthouse -perfect for long stays

BriannaRating, 5 stars6 months ago
Very nice host !! Airbnb was very cozy and accessible, would highly recommend :)
Guest favorite
The exterior features a welcoming entrance with a wooden front door, framed by two large windows. Potted plants are positioned beside the steps, which lead to a small porch. The light yellow siding adds a cheerful touch to the home facade.
Home in Winooski
4.94 out of 5 average rating, 128 reviews

Spacious Winooski Oasis, close to downtown!

GauraviRating, 5 stars3 days ago
We had a great stay here. The house was quaint and exactly as pictured. We asked for recommendations but didn’t receive a response. However, Sam was super responsive for all other things house related like check in time and when the shower pump was broken and only giving us cold water. The hot water issue was taken care of right away which was appreciated! The backyard is big and fenced in. This is great for dogs! There is a grill and fire pit. We didn’t use either but having that amenity was nice. Location is great and so was the price. Walking distance and car ride from most eateries and cute shops. We felt safe, thank you!
Top guest favorite
A warm living area features a stone fireplace beneath a wall-mounted television. Windows allow natural light to illuminate the space, emphasizing the wooden ceiling and a mix of comfortable seating, including a gray sectional, armchair, and an ottoman.
Home in Stowe
4.95 out of 5 average rating, 184 reviews

New Remodel w/VIEWS! on 20 Acres!

Carla Rating, 5 stars1 month ago
Kim was super kind and went above and beyond to help me sort out a situation even before our arrival. The home is located in a quiet beautiful area, it is super comfortable, beautifully decorated. The beds were very comfortable. We had plenty of towels and linens. My kids enjoyed playing games in the basement, and my husband and I enjoyed watching TV and reading by the fireplace. I highly recommend Kim's place.
Top guest favorite
The exterior of Hathaway House is shown, featuring a dark-colored barn structure with multiple windows and a welcoming porch. Lush greenery and flowering plants surround the property, while the roof is styled in a contemporary design. Tall trees form a serene backdrop.
Home in Hartford
4.97 out of 5 average rating, 103 reviews

Luxury Barn Home w/Hot Tub, Sauna, Gardens MtnView

DianeRating, 5 stars3 months ago
This is my second time staying at Hilary’s home, and for good reason! My family loved gathering by the fireplace everyday, using the hot tub and sauna, and cooking dinners for our group of 8 in the well equipped kitchen every night! Plenty of room for us to spread out. Also love how close it is to the town of Woodstock (adorable with great shopping!) Hilary is very responsive and I am sure we will be back for a 3rd time at some point.
Guest favorite
A large, colonial-style house with a white exterior features multiple gabled roofs and symmetrical windows. A manicured lawn surrounds the home, with shrubs and two mature trees adding to the spacious setting. Blue skies provide a bright backdrop.
Home in Colchester
4.96 out of 5 average rating, 125 reviews

Lake Champlain Colonial

JohnRating, 5 stars2 months ago
⭐️⭐️⭐️⭐️⭐️ Fantastic Stay! I had a wonderful stay at Tamaras’s place! It was spotless, cozy, and well-equipped with thoughtful touches. The location was perfect/close to everything yet peaceful. Tamara was super responsive and helpful. Highly recommend and would stay again!

Private house rentals

Guest favorite
A covered patio area features several adirondack chairs arranged around a small table, overlooking Lake Champlain. Tall trees and plants provide natural framing, with a clear view of the water in the background. Hints of decorative elements add charm to the outdoor space.
Home in Milton
4.95 out of 5 average rating, 84 reviews

Waterfront * Sunsets * Private * Swimming/Fishing

KevinRating, 5 stars3 months ago
On our last day we saw a spectacular sunset which was indicative of our whole stay. The star was of course the wonderful setting on the lake. It was enhanced by how tastefully the house was renovated, decorated and fully supplied with everything we needed. It truely exceeded our expectations and made for a memorable experience in the beautiful state of Vermont.
Guest favorite
Home in Warren
4.97 out of 5 average rating, 102 reviews

Bluebird Cottage - Three Min to Sugarbush Resort

WhitneyRating, 5 stars4 days ago
Colin's place was great for our Easter with our four children and two grandchildren. Location is convenient to Sugarbush and surrounding attractions.
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
A cozy living area features a plaid couch and two wooden chairs arranged around a coffee table. A view of the kitchen is visible through an open doorway. Natural light filters through a partially open window with light curtains. A simple clock and artwork adorn the walls.
Home in Morrisville
4.92 out of 5 average rating, 12 reviews

Morrisville's Cottage Style Coziness

DianaRating, 5 stars12 months ago
Sherry's cottage was the perfect place for our family to view the eclipse from! The place was well-equipped with everything we needed and spotless. Would definitely stay again!
Superhost
The exterior of the rural country home is set on a grassy expanse, featuring a modern design with large glass windows. A stone chimney is present, and comfortable seating options are arranged on the front patio. Lush greenery and wildflowers frame the foreground.
Home in Bakersfield
4.91 out of 5 average rating, 156 reviews

Northern Vermont Country Escape/ The Martin House

ViktorRating, 5 stars1 month ago
Thank you very much, Robin. The house is located in a cozy picturesque place. The weekend was wonderful. The house has all the amenities, and the hot tub is just super. We went skiing in the neighboring resorts, saw the sights. I recommend this wonderful place.
Superhost
Home in Grand Isle
4.87 out of 5 average rating, 156 reviews

Gorgeous 1835 Farmhouse w. Lake/MTN Views!

Maria Del CarmenRating, 5 stars3 months ago
It is a beautiful house where you can smell the family and we liked that a lot. It is close to the ski slopes, very clean and comfortable. Lidsa and Tom have very good communication, excellent service.
Guest favorite
The exterior of the post and beam house features a green metal roof and a spacious wrap-around deck. A hot tub is located prominently on the deck, surrounded by landscaped grass and trees. Outdoor seating is arranged on the deck, inviting relaxation.
Home in Stowe
4.94 out of 5 average rating, 189 reviews

Huge deck, hot tub, foosball, surrounded by nature

MaritaRating, 5 stars3 weeks ago
Great stay at Jen’s beautiful chalet. Easy to communicate with and well equipped with many kitchen supplies and all the needed towels, linens, hairdryers, and a thoughtful welcome package. Only about 15 mins from the mountain and 10 mins to town. Thanks!
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 Middlesex

  • Total rentals

    70 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    5.9K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Washington County
  5. Middlesex
  6. House rentals