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Featured Cottages in Thimble Islands

New Haven Gem w/ Private Pool, Walk to Beach!
Front of property

New Haven Gem w/ Private Pool, Walk to Beach!

3.0 star property
New Haven Gem w/ Private Pool, Walk to Beach!
Guilford Carriage House at Granite Lodge!
Relax in this spacious living area with a high ceiling and exposed beams, featuring a large sofa and armchair, wooden coffee table, and dining area.

Guilford Carriage House at Granite Lodge!

3.0 star property
10.0 out of 10, Exceptional, (1)
"I’m normally not one to leave reviews but I had to for The Carriage House! Everything from the homey, relaxing feel to the great views was amazing! My friends and I wanted to extend our stay lol. We’re already planning another stay here for a summer trip! Also appreciated the host’s friendliness and ensuring we had an enjoyable experience. 10/10"
Guilford Carriage House at Granite Lodge!
Elegant Middlefield Getaway w/ Game Room!
Relax in a serene garden setting with a circular table and Adirondack chairs.

Elegant Middlefield Getaway w/ Game Room!

3.0 star property
Elegant Middlefield Getaway w/ Game Room!
Cozy Westbrook Vacation Rental - Walk to Beach!
Guests can enjoy stunning sea views from this property, with kayaks available for use.

Cozy Westbrook Vacation Rental - Walk to Beach!

3.0 star property
4.0 out of 10, (1)
"The property was clean. The pictures in the ads made it clear that it was supposed to be a waterfront property. It was not. The pictures were taken on a neighbors private property that actually does sit on the water. The fireplace did not work. The only beach access was through a public park which was immediately next to the house. There were several slats missing from the blinds in the bedroom facing the parking lot which was about 8 feet away. Very disappointing for what was supposed to be a...
Cozy Westbrook Vacation Rental - Walk to Beach!
Bright Milford Beach House w/ Outdoor Shower
Relax on the covered porch with two Adirondack chairs, taking in the view of the surrounding neighborhood.

Bright Milford Beach House w/ Outdoor Shower

3.0 star property
Bright Milford Beach House w/ Outdoor Shower
Beachfront Connecticut Retreat w/ Views!
Enjoy stunning views of the beach from this room, featuring a table and chair, and a door with an ornate design.

Beachfront Connecticut Retreat w/ Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great spot on the ocean with an amazing host!"
Beachfront Connecticut Retreat w/ Views!
Walkable New Haven Retreat w/ Ocean Views!
Enjoy a scenic waterfront view from the paved walkway at Pardee Seawall Park.

Walkable New Haven Retreat w/ Ocean Views!

3.0 star property
Walkable New Haven Retreat w/ Ocean Views!
Waterfront Cottage w/ Sunroom + Patio & Grill
Enjoy a serene view of the water and lush surroundings from this room's large window.

Waterfront Cottage w/ Sunroom + Patio & Grill

3.0 star property
Waterfront Cottage w/ Sunroom + Patio & Grill
Westbrook Home w/ Ocean Views - Walk to Beach
Enjoy cooking in this well-equipped kitchen with a central island, dishwasher, and sink.

Westbrook Home w/ Ocean Views - Walk to Beach

3.0 star property
Westbrook Home w/ Ocean Views - Walk to Beach
Dreamy Waterfront Westbrook Home on Private Beach
Interior

Dreamy Waterfront Westbrook Home on Private Beach

3.0 star property
Dreamy Waterfront Westbrook Home on Private Beach
Charming Old Saybrook Home: Half-mi to Sand & Sea!
Compact kitchen with a wooden table, microwave oven, and window with blinds.

Charming Old Saybrook Home: Half-mi to Sand & Sea!

3.0 star property
Charming Old Saybrook Home: Half-mi to Sand & Sea!
Charming Westbrook Cottage, Steps to Private Beach
Enjoy cooking in this well-equipped kitchen with oven, microwave, and refrigerator.

Charming Westbrook Cottage, Steps to Private Beach

3.0 star property
Charming Westbrook Cottage, Steps to Private Beach
Walk to Beaches: Sunny East Haven Home w/ Grill
Enjoy a serene beach experience with access to calm waters and a picturesque shoreline.

Walk to Beaches: Sunny East Haven Home w/ Grill

3.0 star property
Walk to Beaches: Sunny East Haven Home w/ Grill
3 Mi to Dtwn: Gem w/ Patio & Fire Pit in New Haven
Fully equipped kitchen with refrigerator, microwave, oven, and dishwasher.

3 Mi to Dtwn: Gem w/ Patio & Fire Pit in New Haven

3.0 star property
3 Mi to Dtwn: Gem w/ Patio & Fire Pit in New Haven
BBQ Ready: Quiet Connecticut Retreat w/ Fire Pit
Interior

BBQ Ready: Quiet Connecticut Retreat w/ Fire Pit

3.0 star property
BBQ Ready: Quiet Connecticut Retreat w/ Fire Pit
'grandma's Cottage' w/ Sunroom: Walk to Beach
Cozy cabin with a rustic interior, featuring a kitchen with a stove, oven, and microwave, and a dining area for two.

'grandma's Cottage' w/ Sunroom: Walk to Beach

3.0 star property
'grandma's Cottage' w/ Sunroom: Walk to Beach
Luxe Lake House in Connecticut: Private Dock
Enjoy cooking in this well-equipped kitchen with a central island, bar stools, and ample counter space.

Luxe Lake House in Connecticut: Private Dock

3.0 star property
Luxe Lake House in Connecticut: Private Dock
2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!
Front of property

2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!

3.0 star property
2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!
Charming Hamden Home: 2 Mi to Yale University
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator and ample dining space.

Charming Hamden Home: 2 Mi to Yale University

3.0 star property
Charming Hamden Home: 2 Mi to Yale University
Bright Milford Beach House w/ Outdoor Shower
Property grounds

Bright Milford Beach House w/ Outdoor Shower

2.0 star property
Bright Milford Beach House w/ Outdoor Shower
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.
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Frequently asked questions

How much do cottages in Thimble Islands cost?
Prices for cottages in Thimble Islands range between and per night. No matter your budget, you're sure to find an ideal place to get in tune with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Thimble Islands?
Get in touch with nature in one of the 27 cottages waiting for you in Thimble Islands. To help you choose an ideal place, take advantage of our filters to search for perks or amenities you need.
Why book your cottage in Thimble Islands with Expedia?
We think a getaway should be a walk in the park, so if you're in search of cottages in Thimble Islands at the perfect price, Expedia has got your back. Stick to the budget and select a low-cost option far away from the city rush, or book an upscale cottage to treat your loved ones.