Thimble Islands Holiday Homes
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Featured Holiday Homes in Thimble Islands
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
West Haven CT
During your stay at this holiday home, you'll be within walking distance of Seabluff Beach. Laundry facilities are available. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Küche
Waschmaschine
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!
Westbrook CT
During your stay at this holiday home, you'll be within walking distance of Westbrook Town Beach. Features include laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Küche
Waschmaschine
Large Charming Historic House close to Beaches
Clinton CT
During your stay at this holiday home, you're just a quick walk from Adam Stanton House and General Store Museum. You'll find features such as laundry facilities. A kitchen and 2 bathrooms are available in the holiday home.
Küche
Waschmaschine
Charming beach home, complete with pool & cozy guest house!
Clinton CT
During your stay at this holiday home, you're just a quick walk from Indian River Marina. Enjoy features like an outdoor pool, laundry facilities and an arcade/games room. Free WiFi and a private pool are available in the holiday home.
Pool
Küche
Beach Bungalow, walk to beach, private backyard
West Haven CT
During your stay at this holiday home, you're just a quick walk from Seabluff Beach. You'll find features such as laundry facilities. The holiday home offers a kitchen and 3 bathrooms.
Küche
Waschmaschine
Direkt am Strand - für 8 Personen
Milford CT
During your stay at this holiday home, you're just a quick walk from Pond Point Beach. Enjoy features like laundry facilities. Enjoy your stay with amenities like a kitchen and a washer/dryer in the holiday home.
Küche
Waschmaschine
Salt & Blue - Walk to Beach - Near Tyde Wedding Venue
Milford CT
During your stay at this holiday home, you'll be within walking distance of Walnut Beach. Laundry facilities are available. Free WiFi and a kitchen are available in the holiday home.
Küche
Waschmaschine
The ARLO - Walk to Brewery and Restaurants
Milford CT
During your stay at this holiday home, you're just a quick walk from Housatonic River. A gym, laundry facilities and an arcade/games room are available. A kitchen and a patio are available in the holiday home.
Küche
Waschmaschine
Updated ranch Home 4 minutes from the beach on a quiet end street.
West Haven CT
During your stay at this holiday home, you'll be within walking distance of Seabluff Beach. You'll find features such as laundry facilities. Free WiFi and a kitchen are available in the holiday home.
UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge
Westbrook CT
This holiday home's walkable location gets good marks from our customers. During your stay, you'll be close to Chalker Beach. You'll find features such as laundry facilities. The holiday home offers free WiFi and a kitchen.
Küche
Waschmaschine
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Branford CT
During your stay at this holiday home, you'll be within walking distance of Stony Creek Brewery. You'll find features such as laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
New Madison beach house - Ocean front- Great views- booking Summer 2026
Madison CT
During your stay at this holiday home, you'll be close to Chaffinch Island State Park. Laundry facilities are available. Enjoy your stay with amenities like free WiFi and a private pool in the holiday home.
Pool
Küche
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Riverhead NY
During your stay at this holiday home, you'll be within walking distance of Roanoke Vineyards. 1 hot tub and laundry facilities are available. Enjoy your stay with amenities like free WiFi and in-room jetted baths in the holiday home.
Whirlpool
Küche
Cheerful 3 Bedroom Beach Front Cottage with Fireplace
Milford CT
During your stay at this holiday home, you're just a quick walk from Bayview Beach. Enjoy features like laundry facilities. The holiday home offers free WiFi and in-room jetted baths.
Küche
Waschmaschine
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View all propertiesLowest 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.
Thimble Islands Holiday Homes essential information
Accommodation | 301 Holiday Homes |
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Highest Price | |
Popular accommodation | Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends, Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!, Large Charming Historic House close to Beaches, Charming beach home, complete with pool & cozy guest house!, Beach Bungalow, walk to beach, private backyard, Direkt am Strand - für 8 Personen, Salt & Blue - Walk to Beach - Near Tyde Wedding Venue, The ARLO - Walk to Brewery and Restaurants, Updated ranch Home 4 minutes from the beach on a quiet end street., UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge, BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!, New Madison beach house - Ocean front- Great views- booking Summer 2026, Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons, Cheerful 3 Bedroom Beach Front Cottage with Fireplace, Coastal getaway with water views in every room |