Holiday rentals in Middlesex

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Popular amenities for Middlesex holiday rentals

Stay near Middlesex's top sights

Three Penny Taproom102 locals recommend
Hunger Mountain Coop station82 locals recommend
Sarducci's77 locals recommend
Positive Pie76 locals recommend
Michael's on the Hill68 locals recommend
Hubbard Park55 locals recommend

Other great holiday rentals in Middlesex

Top guest favourite
Home in Plattsburgh
5 out of 5 average rating, 52 reviews

Entire 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 reviews

Burnt 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 reviews

very 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 reviews

Private 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 reviews

Beautiful 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 reviews

Modern 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 reviews

Lovely 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 reviews

Private 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

Destinations to explore

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