
Cottage vacation rentals in Middletown
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Top-rated cottage rentals in Middletown
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middletown cottage rentals
Cottage rentals with a hot tub

Lake View, Hot Tub, 4 Kayaks, Central AC, Fire Pit

Luxury cottage by the sea with hot tub and pool

The Cottage at Blackberry River Inn

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

Lakefront Getaway | Hot Tub | Game Room | Fire Pit

Private Beach Cottage

The Lil Nauti Cottage, Steps To Fairfield Beach

Light-filled cottage
Pet-friendly cottage rentals

Private and Serene home close to I-84 and shopping

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

Charm + location. Walk to beach, town, & harbor.

Charming Fairfield Beach 3BR Cottage By The Sea

Cozy Cottage by the pond

Summer Sale|CozyCottage|Pet-friendly|Walk to Beach

Your Nest Near The Beach

Newly Built Cottage in Housatonic Valley
Private cottage rentals

Charming 3 bedroom cottage on Lake Pocotopaug

Waterfront Beach Cottage in Connecticut

Cozy Lakefront Cottage Perfect for Families

Enchanted Cottage on the Marsh, walk to beach

Cute cottage near UConn, lake, and restaurants.

Bucolic Farm On A Country Road

The House on the Hill

Serene Waterfront Cottage
Destinations to explore
- Plainview Vacation rentals
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- Rentals with outdoor seating Middletown
- House rentals Middletown
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- Rentals with a washer and dryer Middletown
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- Rentals with a fireplace Middletown
- Family-friendly rentals Middletown
- Rentals with a patio Middletown
- Pet-friendly rentals Middletown
- Rentals with a fire pit Middletown
- Cottage rentals Connecticut
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- Beach
- Fairfield Beach
- Yale University
- Foxwoods Resort Casino
- Six Flags New England
- Cooper's Beach, Southampton
- Ocean Beach Park
- TPC River Highlands
- Shinnecock Hills Golf Club
- Walnut Public Beach
- Woodmont Beach
- Jennings Beach
- Thunder Ridge Ski Area
- Silver Sands Beach
- Brownstone Adventure Sports Park
- Groton Long Point Main Beach
- Amagansett Beach
- Bushnell Park
- Sandy Beach
- Cedar Beach
- Seaside Beach
- South Jamesport Beach
- Sherwood Island State Park
- Long Island Aquarium