
Holiday houses 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

Apartment in Southbury
4.71 out of 5 average rating, 31 reviewsPrivate Apt in Southford/Southbury

Farm stay in Bethlehem
4.75 out of 5 average rating, 44 reviewsThe Loft @ Sun One Organic Farm

Cottage in Woodbury
4.6 out of 5 average rating, 5 reviewsThe serenity farm cottage

Apartment in Waterbury
4.67 out of 5 average rating, 3 reviewsStylish 3BR Retreat in Waterbury
Guest favourite

Home in Woodbury
4.9 out of 5 average rating, 61 reviewsFamily-Friendly Woodbury Home with Yard + Deck!

Home in Middlebury
4.71 out of 5 average rating, 7 reviewsLake Quassapaug Homestead

Guest suite in Middlebury
4.89 out of 5 average rating, 46 reviewsCountry Retreat Near Lake Quassapaug

Apartment in Southbury
5 out of 5 average rating, 4 reviewsCozy Connecticut getaway!
Destinations to explore
- Hudson Valley Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- The Hamptons Holiday rentals
- East River Holiday rentals
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- Yurt Rentals United States
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- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
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- Holiday Chalets United Kingdom
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- Apartments with a Hot Tub United States
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- Beach Houses United Kingdom
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- Pet-Friendly Vacation Rentals United States
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- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Hudson Highlands State Park
- Walkway Over the Hudson State Historic Park
- Caumsett State Park