
Holiday rentals in Middlesex
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Top-rated holiday rentals in Middlesex
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Middlesex
Top guest favourite

Home in Plattsburgh
5 out of 5 average rating, 52 reviewsEntire New Lake House, private deck, large lawn
ElizabethRating, 5 stars4 months ago
This exceptional lake house provided the most welcoming space we could have asked for to celebrate our family and to spend time together. From heated floors on the cool nights to the beautiful piano to the awesome "grown-up-sized" Jenga, we filled our days with settling in together and simply enjoying! We are so grateful for Dina to sharing this wonderful home with us!!
Guest favourite

Home in Montgomery
4.91 out of 5 average rating, 11 reviewsBurnt Mountain: modern getaway near Jay Peak
MatthewRating, 5 stars1 month ago
I have stayed in a many rental properties over the years and I have never had a kitchen so loaded with everything a cook could ask for - very helpful! Amazing views and a 20 minute drive to Jay - just a great experience. The property is on a dirt road, which is no joke. Make sure you have the right vehicle for Vermont mud season and you will have the time of your life. Highly recommended!
Guest favourite

Holiday home in Rutland
4.93 out of 5 average rating, 61 reviewsvery nice vacation rental 20 min from Killington
TaiRating, 5 stars1 month ago
This was my second stay and I enjoyed it as much as the first. Easy to get in and out. The place is warm, shower is hot, things are clean.
Superhost

Cabin in Barnard
4.8 out of 5 average rating, 15 reviewsPrivate post & beam log cabin on Macintosh Pond.
NinaRating, 5 stars4 months ago
It was perfect for what we wanted! We were giving Grandma an 80th Hallmark Experience. A lot of what we did was in Woodstock and it was a noce 30 min ride to the town, but for us very convenient. We had a family of 14 and we played games in ythe main living room all together. The downstairs was perfect for our older kids to hang out in!
Superhost

Villa in Stowe
4.82 out of 5 average rating, 45 reviewsBeautiful 5 Bedroom Villa with Amazing Views
RichardRating, 5 stars3 months ago
Very nice home with great amenities. Great location to and from everything. Nicely distributed with space for everyone. Beds were comfortable and the home has plenty of towels etc. Overall it was a great place for weekend or longer. Maria was easy to communicate with and there were no issues.
Top guest favourite

Home in Chittenden
5 out of 5 average rating, 8 reviewsModern Retreat next to Mountain Top Inn,Killington
MaddyRating, 5 stars2 months ago
I couldn't recommend this place more! My cousins and I had a great time and Uli is super attentive. The hot tub has a great view of the lake, it was also salt water which I love. The space was extremely cozy and exactly what we needed. We snowboarded pico and killington and it was about a 25-30 minute ride. We will for sure be back! Thank you guys so much!
Guest favourite

Flat in Burlington
4.97 out of 5 average rating, 67 reviewsLovely 1 bedroom
Tyson & Tara GranlieRating, 5 stars6 months ago
Highly recommended space and host! Kurt is hands down an A+ super host! We arrived in Burlington in the evening with having another Airbnb reservation that we found not to be a good fit for us! Frantically searching for other Airbnb accommodations for the night, several hosts had availability but showed no urgency to help us. Kurt literally stopped what he was doing to go and turn lights and heat on for us. He also left water, a couple beers, and creamer in the fridge for our morning coffee, which too was provided. The space is exactly how it was pictured. Clean, uncluttered, and beautiful! Kurt’s place has great location in a charming quiet neighborhood with driveway parking. Comfortable bed and great water pressure in the shower was also great to have! Finding this place last minute was the cherry on top of our amazing Burlington experience….and we will be back! Thanks again
Top guest favourite

Home in Warren
4.97 out of 5 average rating, 39 reviewsPrivate Home with Hot Tub 1 mile from Sugarbush
ThomasRating, 5 stars1 month ago
We had an amazing stay at Don’s place. The location was perfect, allowing us to enjoy four great days of skiing. Don was a fantastic host, making everything easy from start to finish. The house was ideal for our extended family of eight, offering plenty of space and comfort. If you’re looking for a spacious, well-located home near Sugarbush, I highly recommend staying here!
Quick stats about holiday rentals in Middlesex
Total rentals
150 properties
Nightly prices starting at
£30 before taxes and fees
Total number of reviews
13K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
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- Sugarbush Resort
- Jay Peak Resort
- Smugglers' Notch Resort
- Spruce Peak
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