
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
Guest favourite

Treehouse in Waterbury
4.93 out of 5 average rating, 58 reviewsThe Roost - Recharge & Relax
KevinRating, 5 stars2 weeks ago
Amazing place. Right off the road but feels very private. It really was like sleeping in the trees. Sandra is a super helpful and friendly host. The house was comfortable and clean, but it still felt like an adventure! My son and I had a blast:)
Top guest favourite

Home in Waterbury Village Historic District
4.98 out of 5 average rating, 62 reviewsPerry Pond House
KirillRating, 5 stars3 months ago
Great place. Nice location.
Superhost

Cottage in Calais
4.98 out of 5 average rating, 92 reviewsCozy Peaceful Cottage
AdrienneRating, 5 stars7 months ago
Morgan is the perfect host, providing everything necessary to a magical stay in their remarkable cabin. I had complete privacy and quiet, but knew she was readily available if I had any questions or needs. The cabin itself is a wonder of architecture, with every detail carefully thought out and rendered. There are books galore and CDs, the slipper foot bathtub is amazing, and the back patio offers a peaceful view of trees and meadow. The property is dotted with wonderful sculptures by her husband, Alan. I watched the sun rise and set and walked down the very dark night road to look at the stars. The woods are my favorite place to be, and there was no shortage of local hiking trails. The general store just down the street is staffed by very friendly folks, and I bought a new favorite coffee mug made by a local artisan. In short, my stay was everything I hoped it would be, and I would highly recommend it.
Superhost

Guest house in Plainfield
4.87 out of 5 average rating, 60 reviewsCozy 1 bed guest suite Sugarwood home
TeresaRating, 5 stars2 weeks ago
The place was delightful—a very cute getaway without being completely remote. The space was perfect for two people. It had everything you needed, and it was very cozy and spacious. I highly recommend it. Jungwood was extremely communicative and helpful during the stay.
Guest favourite

Guest suite in Montpelier
4.92 out of 5 average rating, 74 reviewsFarmhouse Sunset Studio at Anderbell Acres
WilsonRating, 5 stars4 months ago
My partner and I had a great time at the guest suite. We hope to stay again in the future.
Top guest favourite

Home in Waterbury Village Historic District
4.94 out of 5 average rating, 36 reviewsWaterfall Oasis with Large Deck
BethRating, 5 stars1 day ago
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.
Top guest favourite

Flat in Waterbury
5 out of 5 average rating, 20 reviews"Stowebury" Apartment
TiffanyRating, 5 stars2 weeks ago
Dan’s place was even better than we expected.! You could tell a lot of thought was put into making the space very comfortable with added touches to make you feel at home. While the space is smaller, it has everything that you would need. We were bummed that it rained on the evening that we planned to use the fire pit but it looked like a nice evening spot to relax. I would highly recommend to others!
Superhost

Flat in Montpelier
4.97 out of 5 average rating, 71 reviewsStylish Montpelier 2BR Apt. Walk to town
JenniferRating, 5 stars63 months ago
Lucy is a welcoming and helpful host. The apartment was just perfect; clean, comfortable, nicely decorated and the beds were exceptional! Lucy went the extra mile to have all of the necessary kitchen utensils and it was so to have a washer and dryer right in the apartment. The location was perfect with great walks right out the door.
Quick stats about holiday rentals in Middlesex
Total rentals
150 properties
Nightly prices starting at
₹3,443 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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- Rentals with a washing machine and dryer Middlesex
- Family-friendly rentals Middlesex
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- Family-friendly rentals Middlesex
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- Rentals with outdoor seating Middlesex
- Rentals with a patio Middlesex
- Rentals with a firepit Middlesex
- Flat rentals Middlesex
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