
Vacation rentals in Middlebury
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Top-rated vacation rentals in Middlebury
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Middlebury vacation rentals
Other great vacation rentals in Middlebury
Guest favorite

Home in Watertown
4.89 out of 5 average rating, 57 reviewsTiny Home Away From Home - Complete Privacy, Peace
Top guest favorite

Barn in Roxbury
5 out of 5 average rating, 56 reviewsFully Renovated Rural Barn
Guest favorite

Guest suite in Wolcott
4.91 out of 5 average rating, 66 reviewsModern cozy, pet friendly
Guest favorite

Guest suite in Woodbury
4.97 out of 5 average rating, 31 reviewsNewEngland Apart/Woodbury Bike trail&Peaceful!
Guest favorite

Cottage in Southbury
4.95 out of 5 average rating, 22 reviewsSun Filled Cottage
Guest favorite

Vacation home in Woodbury
4.88 out of 5 average rating, 32 reviewsUNIQUE and GORGEOUS historic loft style rental
Guest favorite

Guest suite in Watertown
4.98 out of 5 average rating, 81 reviewsPrivate King suite w/ separate entry-Walk to Taft!
Guest favorite

Home in Watertown
4.81 out of 5 average rating, 62 reviewsCozy Cottage
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Jersey Shore Vacation rentals
- Mount Pocono Vacation rentals
- South Jersey Vacation rentals
- Yale University
- Fairfield Beach
- Rye Beach
- Six Flags New England
- Walnut Public Beach
- Rye Playland Beach
- Thunder Ridge Ski Area
- Rowayton Community Beach
- TPC River Highlands
- Cedar Beach
- Brownstone Adventure Sports Park
- Silver Sands Beach
- Bash Bish Falls State Park
- Woodmont Beach
- Sunken Meadow State Park
- Sandy Beach
- Jennings Beach
- Wildemere Beach
- Seaside Beach
- Hudson Highlands State Park
- Kent Falls State Park
- South Jamesport Beach
- Harveys Beach
- Long Island Aquarium