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

Luxury Condo Tucked in the Heart of Killington
Very nice place easy access to routes 4 and 100 with plenty of things to do

Vermont Summer Retreat
This was our second year staying at this beautiful home in Waterbury VT- we just loved it so much! Area is conveniently located in Waterbury and close to Stowe. We loved being by the woods and the river in the backyard. Toys for our kids at the home was very appreciated as was the little kids teepee! Owners were proactive in communication and so thoughtful with details throughout the house to make the stay comfortable and have us feel at home!

Epic Views of the Green Mountains
We had a great stay at William’s. The location was beautiful and the house was comfortable. We had a great mix of day-tripping and relaxing with a view. We also ran into William and he was very helpful and friendly.

Ranch at Mendon Mt Orchards
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!

SugarBear- Pool, AC, Sauna, Gym, Tennis!
Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.

Charming Barre Getaway
This was a very beautiful Airbnb made very comfortable by Karen the host. Everything you could ever want or need on vacation was in this home. It was so comfortable and clean one of the best Airbnb‘s that my family has ever stayed in. We will recommend it to other family members that may be visiting the area as we have moved out of state . I recommend this to anyone looking for a wonderful peaceful place to stay enjoying Vermont in any season! The care that was taken in this beautiful home has inspired us to look into staying at Karen‘s Airbnb in Burbank California when we visit our son. This is way beyond five stars.!

Luxury Alpine Studio. Ski In Ski Out. Spruce Peak
This place was perfect for our family of three for a long weekend. The room had everything we needed and the views of the village from the balcony were amazing. Lots to do in the village and plenty more just a short drive down the road to Stowe. We’d love to come back in the summer when there are more outdoor activities available.

The Vista - 180º Mt. views w/Pool 12min to Stowe
Look no further if you're traveling with toddlers—this Airbnb is a dream for families! The location is perfect: tucked just outside of Stowe, it offers peaceful country vibes, a spacious backyard, and stunning mountain views from every window—all while being just a short drive from town. What really sets this home apart is how toddler-friendly it is. It's a BabyQuip heaven—stocked with everything from a high chair and nugget couch (iykyk!), to Fisher Price Little People toys, coloring supplies, a train set, games, and more. Our toddler had a blast and was perfectly content spending evenings at the house, thanks to the endless entertainment options. The host went above and beyond—the home was spotless, and the kitchen was fully equipped with all the essentials. Highly recommend for any family looking for a relaxing, kid-friendly escape in Vermont!
Weekly house rentals

Modern Dwell Home +Sauna between Stowe/Waterbury
Fabulous stay. Amazing home that we didn’t want to leave! Loved the kitchen and Sonos surround sound. My 2 kids had a blast playing outside in the snow. Hayden was a great host and has a truly unique place. Would love to see it in the summer!

The Vermont Red Barn
Great location and private property in the woods. Property was clean, comfortable, plenty of room and close to downtown Leah was responsive from beginning to end, had all the instructions and even allowed us to check-in early. Highly recommend this property if you are visiting this area.

Spacious Eco-Friendly Stowe Home for Family Fun
A beautiful Stowe getaway. The house has beautiful views of Mt. Mansfield, boasts plenty of space, and is in a great location relative to town.

Panoramic Mountain Views. Quiet, Private & Clean.
We had an absolutely wonderful stay here! The house and views were so beautiful! Home was very clean and pretty much had every thing you need. She had toys and chairs for the beach for the kids which was awesome! Mary Anne was very accommodating when we told her that we had family coming through Vermont and let them stay with us for night! So great and grateful! Location is very peaceful and very well kept and would definitely come back and stay here! Thank you again for everything!

Perry Pond House
Great place. Nice location.

Waterfall Oasis with Large Deck
If you have the opportunity to stay at this amazing home, do it. The bridge leads you to a private and beautiful home that is exactly what you would expect from the pictures. The hosts are friendly, responsive and helpful. The home was the best stocked Airbnb I have ever stayed at. So welcoming and so many thoughtful touches. We used the grill to cook dinner on the deck overlooking the waterfall, watched fireflies in the field in the evening and enjoyed coffee from the living room every morning. We also going Waterbury to be a perfect location for exploring Vermont.

Cozy home with mountain views
Great little secluded place for a quiet, relaxing time, but also very close to Stowe and a number of great shops and restaurants. Joe was very responsive and actually brought me a water hose so I could fill my cold plunge. I enjoyed my stay and would recommend to others looking to unwind.

Fresh Summer Getaway, stunning Mountain Views!
Our family enjoyed our stay at Charles and Tara’s place. I appreciated the detailed instructions and information they gave us about the property. We enjoyed the incredible views and spent peaceful moments in the hot tub. We couldn’t have asked for a better place to stay, we highly recommend booking! We hope to be back soon.
Private house rentals

Cozy Lake Cottage
The cozy cottage was exactly as described and pictured. Beautiful and thoughtful design and furnishings. Gorgeous views and comfortable beds. Proactive communication about cell service and one inconsequential blemish on the deck due to a storm and back ordered part. So clean it feels brand-new!

The 1919 Mountain Farmhouse (Hot Tub coming July!)
We came to Vermont for a wedding and Elizabeth’s place was perfect! The house is beautiful and felt like home! We enjoyed being close to Montpelier and Barre, but also being a bit secluded. The house has a beautifully modern country feel.

Pond House
I recently stayed at this beautiful home with two friends for my birthday celebration, and we couldn’t have asked for a better experience! The house was absolutely stunning—spotlessly clean, beautifully decorated, and incredibly comfortable. The beds were especially comfy. Our hosts were so accommodating and made sure we had everything we needed for a perfect stay. The peaceful surroundings and cozy atmosphere made it a truly special getaway. We’re so grateful for the wonderful hospitality and would love to return in the future. Highly recommend!

Charming Farmhouse near Maple Corners
Wonderful property. Owners very responsive. Tucked away but a short trip to all amenities one could ever want. We’ve stayed in Calais and Maple Corner several times and absolutely love the area. Loved the quiet walk up Emslie to the VAST trail with our dog. It was a great morning ritual that took us a few miles to Maple Corner Store for a breakfast sandwich before heading back home to enjoy all the other activities the area has to offer. Wonderful game and puzzle selection along with comfy couches to enjoy restful evenings. Nice kitchen with lots of space. House was clean and inviting.

Huge Waterbury home near Stowe with views/sauna
The Waterbury home was a perfect retreat for our family of 8 celebrating a graduation in nearby Burlington. It was quiet, spacious, and well appointed. My family truly felt at home, and commented multiple times they wish it was closer to home so we could stay again! Jenny was an awesome host, super responsive to my questions and requests, and great to work with to make our weekend in Vermont special.

Rivertop Retreat- Hot tub, Riverwalk!
My friend and I needed a night to escape traffic & the busy life. We had such a great experience here! It's in a great location, walking distance to the river. Super close to the covered bridge and waterfall. The rooms are clean and adorable, the yard is comfortable and the hot tub was perfection! We will be here again!

Cozy net zero apartment
I stayed for 2 nights in early May for my son's graduation from Norwich. I was very happy with the close proximity to the University. The place was nice and clean and felt very homey. very quiet and peaceful. I would stay again.

Charming and Centrally Located Waitsfield Home.
Very comfortable stay in a beautiful setting.
Quick stats about house rentals in Middlesex
Total rentals
70 properties
Nightly prices starting at
₹5,165 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
- Bolton Valley Resort
- Spruce Peak
- Jay Peak Resort Golf Course
- Pico Mountain Ski Resort
- Cannon Mountain Ski Resort
- Cochran's Ski Area
- Dartmouth Skiway
- Fort Ticonderoga
- Pump House Indoor Waterpark
- Autumn Mountain Winery
- Mt. Eustis Ski Hill
- Northeast Slopes Ski Tow
- Ethan Allen Homestead Museum
- Vermont National Country Club
- Cozy Cottages & Otter Valley Winery
- Leahy Center for Lake Champlain
- Country Club of Vermont
- Montshire Museum of Science
- Burlington Country Club
- Lincoln Peak Vineyard
- Killington Adventure Center