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Jun 27 - Jun 29
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Aug 15 - Aug 17

Cottages in Thimble Islands

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

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

3.0 star property
New Haven Gem w/ Private Pool, Walk to Beach!
Elegant Middlefield Getaway w/ Game Room!
Interior

Elegant Middlefield Getaway w/ Game Room!

3.0 star property
Elegant Middlefield Getaway w/ Game Room!
Bright Milford Beach House w/ Outdoor Shower
Interior

Bright Milford Beach House w/ Outdoor Shower

3.0 star property
Bright Milford Beach House w/ Outdoor Shower
Beachfront Connecticut Retreat w/ Views!
Dining

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!
Guilford Carriage House at Granite Lodge!
Interior

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!
Walkable New Haven Retreat w/ Ocean Views!
Interior

Walkable New Haven Retreat w/ Ocean Views!

3.0 star property
Walkable New Haven Retreat w/ Ocean Views!
Waterfront Cottage w/ Sunroom + Patio & Grill
Interior

Waterfront Cottage w/ Sunroom + Patio & Grill

3.0 star property
Waterfront Cottage w/ Sunroom + Patio & Grill
Charming Old Saybrook Home: Half-mi to Sand & Sea!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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

3.0 star property
Charming Old Saybrook Home: Half-mi to Sand & Sea!
Westbrook Home w/ Ocean Views - Walk to Beach
House (2 Bedrooms) | Interior

Westbrook Home w/ Ocean Views - Walk to Beach

3.0 star property
Westbrook Home w/ Ocean Views - Walk to Beach
Cozy Westbrook Vacation Rental - Walk to Beach!
Property grounds

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

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
House (4 Bedrooms) | Interior

BBQ Ready: Quiet Connecticut Retreat w/ Fire Pit

3.0 star property
BBQ Ready: Quiet Connecticut Retreat w/ Fire Pit
Luxe Lake House in Connecticut: Private Dock
Microwave, oven, stovetop, dishwasher

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!
Interior

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 Westbrook Cottage, Steps to Private Beach
Interior

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
Interior

Walk to Beaches: Sunny East Haven Home w/ Grill

3.0 star property
Walk to Beaches: Sunny East Haven Home w/ Grill
'grandma's Cottage' w/ Sunroom: Walk to Beach
Cottage (3 Bedrooms) | Interior

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

3.0 star property
'grandma's Cottage' w/ Sunroom: Walk to Beach
Charming Hamden Home: 2 Mi to Yale University
Interior

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.