Middletown Cottages

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Cottages in Middletown

Waterfront Cottage in Branford

branford CT

Located in Branford, this cottage is by the ocean, within a 10-minute drive of Stony Creek Brewery and Polished.

Hot Tub

Kitchen

Historic cottage in Deep River, CT

Deep River CT

With a stay at this cottage in Deep River, you'll be within a 15-minute walk of Connecticut River and Selden Neck State Park.

Kitchen

Air conditioning

RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.

Westbrook CT

With a stay at this cottage in Westbrook (Westbrook Center), you'll be within a 5-minute drive of Chalker Beach and Westbrook Town Beach.

Pool

Hot Tub

Direct waterfront renovated cottage.

Madison CT

With a stay at this cottage in Madison (Madison Center), you'll be within a 5-minute drive of Deacon John Grave House and Anna Mia's.

Kitchen

Washer

Guilford Carriage House at Granite Lodge!

Guilford CT

Located in Guilford, this cottage is within a 10-minute drive of Bill Miller’s Castle and Orchard Hill Plaza Shopping Center.

Pool

Kitchen

Adorable Cottage with Cottage porch, walk to water & town

Westbrook CT

With a stay at this cottage in Westbrook (Westbrook Center), you'll be within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.

Kitchen

Pet friendly

Charming 3-bedroom cottage short walk to Chalker Beach

Old Saybrook CT

With a stay at this cottage in Old Saybrook (Saybrook Manor), you'll be within a 5-minute drive of Chalker Beach and Saybrook Country Barn.

Kitchen

Washer

Relax with a beautiful lake view

Colchester CT

Located in Colchester, this cottage is on the waterfront, a 1-minute drive from Lake Hayward and 8 minutes from Devil's Hopyard State Park.

Kitchen

Free WiFi

Charming 3-bedroom cottage in Old Saybrook with AC, WiFi

Old Saybrook CT

With a stay at this cottage in Old Saybrook (Saybrook Manor), you'll be within a 5-minute drive of Saybrook Country Barn and Crystal Lake Town Park.

Kitchen

Washer

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

Westbrook CT

Located in Westbrook, this cottage is by the ocean, a 5-minute drive from Clinton Plaza Shopping Center and 6 minutes from Adam Stanton House and General Store Museum.

Kitchen

Washer

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Clinton CT

Located in Clinton, this cottage is within a 5-minute drive of Indian River Marina and Adam Stanton House and General Store Museum.

Kitchen

Washer

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

East Hampton CT

With a stay at this cottage in East Hampton (Lake Pocotopaug), you'll be within a 10-minute drive of Lake Terramuggus and Comstock Bridge.

Kitchen

Washer

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.