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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Browse Select Thimble Islands Cottages

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Pool

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

9.6 out of 10, Exceptional, (37)
"Lovely cottage beautifully decorated, close to restaurants, farm stands, and food stores. A least a 15 to 20 minute walk to the beach."
The price is £303
includes taxes & fees
2 Jul - 3 Jul
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Historic Whitneyville Cottage
Fridge, microwave, oven, stovetop

Historic Whitneyville Cottage

9.6 out of 10, Exceptional, (14)
"My wife and I, and our little dog, had a great experience staying at the Yellow Cottage. For our needs, it was perfectly located. It's on a busy street, but the traffic noises wound down at night. Much nicer than the hotels in the area."
Historic Whitneyville Cottage
Beachside Branford- walk to Beach, Grill
Dining

Beachside Branford- walk to Beach, Grill

10.0 out of 10, Exceptional, (3)
"Charming little cottage that was just right for our trip to the CT shoreline."
Beachside Branford- walk to Beach, Grill
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (26)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is £183
includes taxes & fees
30 Jun - 1 Jul
1-bedroom cottage with Grove Beach 🏖️ access.
Direct waterfront cottage on private sandy beach
Exterior

Direct waterfront cottage on private sandy beach

10.0 out of 10, Exceptional, (4)
"Enjoyed our stay very much. Cute cottage, rustic. Only downside was the airport is close "
Direct waterfront cottage on private sandy beach
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Exterior

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (73)
"Perfect and cozy home base for visiting with family!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Beachfront Connecticut Retreat w/ Views!
TV

Beachfront Connecticut Retreat w/ Views!

9.6 out of 10, Exceptional, (7)
"Just a wonderful beach cottage in a great spot that had all we needed"
Beachfront Connecticut Retreat w/ Views!
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
Outdoor dining

Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more

10.0 out of 10, Exceptional, (2)
"Wonderful stay in a remodeled stone house. Host was great and the house is very comfortable. We really enjoyed the beautifully restored building and all the touches throughout. "
The price is £391
includes taxes & fees
29 Jun - 30 Jun
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Interior

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

8.0 out of 10, Very good, (3)
"Very quiet, clean and quaint little cottage."
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Direct waterfront renovated cottage.
TV, books

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (73)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.
The Dream Location for Your Perfect Vacation
3 bedrooms, desk, free WiFi, bed sheets

The Dream Location for Your Perfect Vacation

9.8 out of 10, Exceptional, (17)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Fridge, microwave, oven, stovetop

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

10.0 out of 10, Exceptional, (2)
"A perfect stay - John and his family were truly wonderful. The house is attached to thier main house, but also very private and secure. We were in town for a wedding weekend and this was the perfect spot for us - truly a beatuiful property! John was helpful in telling us about all of the local spot and supplying us with everything we needed. His wife even welcomed us with a cheese board and wine! Thanks John and family - we had a great time!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
New Haven Gem w/ Private Pool, Walk to Beach!
House (3 Bedrooms) | 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!
1930s Waterfront Cottage on Tuttle's Point
Interior

1930s Waterfront Cottage on Tuttle's Point

9.8 out of 10, Exceptional, (27)
"We loved our time at Little White Top. The house is super clean and has large bedrooms and a really well-stocked kitchen. The big screened porch overlooking the water was a perfect place to play games, eat and just hang out. On calm days we enjoyed kayaking off the beach just down the road. We hope to stay here again!"
1930s Waterfront Cottage on Tuttle's Point
Charming 3-bedroom cottage in Old Saybrook with AC, WiFi
Fridge, microwave, oven, dishwasher

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

10.0 out of 10, Exceptional, (2)
"We had a lovely stay. Everything was as described on the listing and the house had everything we needed for our family. It was great to have the grill and a kitchen with all the supplies needed. The area is lovely and quiet with two small but nice private beaches within walking distance"
Charming 3-bedroom cottage in Old Saybrook with AC, WiFi
Beach cottage on private beach!
Dining

Beach cottage on private beach!

10.0 out of 10, Exceptional, (4)
"It was a very nice cottage. Great price for staying right on the beach"
Beach cottage on private beach!
Charming Westbrook Cottage, Steps to Private Beach
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils

Charming Westbrook Cottage, Steps to Private Beach

9.8 out of 10, Exceptional, (6)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach
Charming newly renovated 2-bedroom cottage in delightful Woodcliff Park
2 bedrooms, free WiFi, bed sheets

Charming newly renovated 2-bedroom cottage in delightful Woodcliff Park

2.0 star property
Charming newly renovated 2-bedroom cottage in delightful Woodcliff Park
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Smart TV

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

9.8 out of 10, Exceptional, (70)
"We stayed at this property last year and again this year. You can’t beat the location and the house is perfect for a group of family or friends. We had a lovely time and look forward to another stay in the future!"
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Waterfront Cottage in Branford
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (94)
"House is beautiful and the view even better. On the waters edge and very quiet grandkids were occupied and very happy "
Waterfront Cottage in Branford
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 £183 and £391 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 103 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.