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

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

Barn in Roxbury
5 out of 5 average rating, 55 reviewsFully Renovated Rural Barn
Guest favourite

Guest suite in Wolcott
4.91 out of 5 average rating, 65 reviewsModern cozy, pet friendly
Guest favourite

Guest suite in Woodbury
4.97 out of 5 average rating, 29 reviewsNewEngland Apart/Woodbury Bike trail&Peaceful!
Guest favourite

Guest suite in Watertown
4.96 out of 5 average rating, 46 reviewsHidden Serenity at TuKasa - Pool & Billiards
Guest favourite

Cottage in Southbury
4.95 out of 5 average rating, 22 reviewsSun Filled Cottage
Top guest favourite

Guest suite in Watertown
5 out of 5 average rating, 80 reviewsPrivate King suite w/ separate entry-Walk to Taft!
Guest favourite

Home in Watertown
4.82 out of 5 average rating, 61 reviewsCozy Cottage
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Mount Pocono Holiday rentals
- South Jersey Holiday 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
- Woodmont Beach
- Bash Bish Falls State Park
- Sandy Beach
- Sunken Meadow State Park
- Jennings Beach
- Wildemere Beach
- Seaside Beach
- Hudson Highlands State Park
- Harveys Beach
- South Jamesport Beach
- Sherwood Island State Park
- Long Island Aquarium