
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
Superhost

Home in Woodbury
4.95 out of 5 average rating, 19 reviews2 homes in one (in-law design) w/salt water pool
Guest favourite

Home in Southbury
4.91 out of 5 average rating, 23 reviewsCozy Family and Pet friendly 3 br Home
Guest favourite

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

Guest house in Sandy Hook
4.93 out of 5 average rating, 71 reviewsThe Nest. Large studio in the Woods.
Top guest favourite

Guest suite in Plymouth
4.93 out of 5 average rating, 61 reviewsSecluded | Cozy | Nature
Guest favourite

Flat in Waterbury
4.88 out of 5 average rating, 40 reviewsKG Comfortable living.
Top guest favourite

Guest house in Newtown
4.99 out of 5 average rating, 70 reviewsGuest Suite at Wisteria Gardens
Guest favourite

Flat in Watertown
4.91 out of 5 average rating, 11 reviewsTaft School Watertown/Oakville
Destinations to explore
- Hudson Valley Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- The Hamptons Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
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- Philadelphia Holiday rentals
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- Cabin Rentals Australia
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- Apartments with a Hot Tub United States
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- Dog-Friendly Cottages United Kingdom
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- Fairfield Beach
- Yale University
- Rye Beach
- Six Flags New England
- Rye Playland Beach
- TPC River Highlands
- Walnut Public Beach
- Woodmont Beach
- Jennings Beach
- Thunder Ridge Ski Area
- Taconic State Park
- Silver Sands Beach
- Bushnell Park
- Calf Pasture Beach
- Seaside Beach
- Sherwood Island State Park
- Rye Town Beach
- Sunken Meadow State Park
- Quotonset Beach
- Cedar Beach
- South Jamesport Beach
- Walkway Over the Hudson State Historic Park
- Hudson Highlands State Park
- Caumsett State Park