
House vacation rentals in Middlesex
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Top-rated house rentals in Middlesex
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Popular amenities for Middlesex house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington
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.

Ranch at Mendon Mt Orchards
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!

Winter Wonderful Waitsfield Spacious VT Home w/Spa
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!

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

Charming Barre Getaway
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!

Charming Sugarbush Standalone Condo
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!

Cool Pool, a Private Oasis
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!

Cozy Studio Spruce Peak Lodge Ski in Ski Out | 319
Had another great stay at the lodge! Stephanie was very responsive. Will definitely book with her again!
Weekly house rentals

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

Large New England Home w/ Gorgeous Mountain Views
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.

South Hill Lodge- 5 BR Post & Beam Home
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.

Beautiful guesthouse -perfect for long stays
Very nice host !! Airbnb was very cozy and accessible, would highly recommend :)

Spacious Winooski Oasis, close to downtown!
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!

New Remodel w/VIEWS! on 20 Acres!
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.

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

Lake Champlain Colonial
⭐️⭐️⭐️⭐️⭐️ 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

Waterfront * Sunsets * Private * Swimming/Fishing
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.

Bluebird Cottage - Three Min to Sugarbush Resort
Colin's place was great for our Easter with our four children and two grandchildren. Location is convenient to Sugarbush and surrounding attractions.

FULL HOUSE w/HOT TUB - Waitsfield Common
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.

Morrisville's Cottage Style Coziness
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!

Northern Vermont Country Escape/ The Martin House
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.

Gorgeous 1835 Farmhouse w. Lake/MTN Views!
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.

Huge deck, hot tub, foosball, surrounded by nature
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!

Lovely private house in the mountains
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
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- Sugarbush Resort
- Jay Peak Resort
- Smugglers' Notch Resort
- Spruce Peak
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Jay Peak Resort Golf Course
- Cannon Mountain Ski Resort
- Cochran's Ski Area
- Pump House Indoor Waterpark
- Ethan Allen Homestead Museum
- Fort Ticonderoga
- Mt. Eustis Ski Hill
- Dartmouth Skiway
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Killington Adventure Center
- Cozy Cottages & Otter Valley Winery
- Vermont National Country Club
- Autumn Mountain Winery
- Lincoln Peak Vineyard
- Leahy Center for Lake Champlain
- Burlington Country Club
- Lucky Bugger Vineyard & Winery