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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Thimble Islands

1-bedroom cottage with Grove Beach 🏖️ access.
Relax in comfort with a sofa, throw blanket, and natural light pouring in through the large window.

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (28)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is NZ$463
includes taxes & fees
19 Aug - 20 Aug
1-bedroom cottage with Grove Beach 🏖️ access.
Now has TV + linens - Relaxing 4-bedroom cottage in Westbrook, CT at West Beach
Stunning historical building with a central tower and traditional pitched roof.

Now has TV + linens - Relaxing 4-bedroom cottage in Westbrook, CT at West Beach

9.2 out of 10, Wonderful, (7)
"It was nice and relaxing...walking, swimming, biking, kayaking and beaching. The house was super cool...150 years old! Nice old fashioned laid back beach vacation! Mary the host was wonderful!"
Now has TV + linens - Relaxing 4-bedroom cottage in Westbrook, CT at West Beach
Beachside Branford- walk to Beach, Grill
Dining

Beachside Branford- walk to Beach, Grill

9.8 out of 10, Exceptional, (6)
"Charming little cottage that was just right for our trip to the CT shoreline."
Beachside Branford- walk to Beach, Grill
Direct waterfront renovated cottage.
Relax in this airy living room with a sofa, chest of drawers, and wicker chair, offering a view of the sea.

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (76)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.
Baiting Hollow Cozy Cottage w/Walk-to beach, Wineries, farmstands. horsefarms!
Enjoy a serene beach experience with gentle waves lapping at the shore.

Baiting Hollow Cozy Cottage w/Walk-to beach, Wineries, farmstands. horsefarms!

9.8 out of 10, Exceptional, (8)
"The cabin was super clean. Ken was very easy to get in touch with and super helpful. Would definitely consider renting from again! "
Baiting Hollow Cozy Cottage w/Walk-to beach, Wineries, farmstands. horsefarms!
The gardners Cottage 1 mile from long Island Sound - pet friendly
Relax in a tranquil setting surrounded by lush greenery and trees, with a seating area perfect for casual meals or relaxation.

The gardners Cottage 1 mile from long Island Sound - pet friendly

10.0 out of 10, Exceptional, (16)
"Robin was a great resource about the area. Her property was amazing the cottage was fantastic. Very comfortable and clean. We had a relaxing stay and a great time. We would love to go back again and again!"
The gardners Cottage 1 mile from long Island Sound - pet friendly
Direct waterfront cottage on private sandy beach
Guests can enjoy a serene beach scene with a clear view of the ocean and a nearby lighthouse.

Direct waterfront cottage on private sandy beach

10.0 out of 10, Exceptional, (5)
"Enjoyed our stay very much. Cute cottage, rustic. Only downside was the airport is close "
Direct waterfront cottage on private sandy beach
Historic Whitneyville Cottage
Compact kitchen with a stainless steel refrigerator, double sink, and oven, complete with white cabinetry and a countertop.

Historic Whitneyville Cottage

9.4 out of 10, Exceptional, (16)
"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
DIRECT WATERFRONT PRIVATE BEACH
Guests can enjoy the beach and calm sea from the comfort of their accommodations.

DIRECT WATERFRONT PRIVATE BEACH

9.4 out of 10, Exceptional, (23)
"This rental was perfect. Super clean and comfy with the most amazing views. Loved that it’s right on the water with a private beach. We will definitely book this property again."
DIRECT WATERFRONT PRIVATE BEACH
Beachfront Cottage with panoramic views of Long Island Sound in Madison CT
Smart TV, fireplace

Beachfront Cottage with panoramic views of Long Island Sound in Madison CT

Beachfront Cottage with panoramic views of Long Island Sound in Madison CT
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!
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
Surrounded by lush greenery, this charming house boasts a cozy balcony overlooking the forest.

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

10.0 out of 10, Exceptional, (3)
"Lovely location and host."
The price is NZ$900
includes taxes & fees
14 Aug - 15 Aug
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Relax in comfort with a table and four chairs, perfect for enjoying refreshments and conversation.

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

9.8 out of 10, Exceptional, (72)
"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
Cozy Home near private beach , close to New Haven area colleges Hospitals
Relax in this serene outdoor seating area with a bird-patterned cushion and a vase of fresh flowers.

Cozy Home near private beach , close to New Haven area colleges Hospitals

9.6 out of 10, Exceptional, (64)
"Joel was terrific, very responsive. The “cozy cottage” was everything we were expecting and hoping for. We plan to return."
Cozy Home near private beach , close to New Haven area colleges Hospitals
Charming 3 Bedroom Beach Front Cottage
Enjoy al fresco dining with a view of the ocean from this deck, featuring a table, chairs, umbrella, and grill.

Charming 3 Bedroom Beach Front Cottage

2.0 star property
10.0 out of 10, Exceptional, (4)
"Stayed here while attending the Soundside Fest. Perfect location to be away from the busy Bridgeport area. The water is right there and it’s the perfect space for a weekend get away."
Charming 3 Bedroom Beach Front Cottage
Adorable Cottage with Cottage porch, walk to water & town
Enjoy cooking in this well-equipped kitchen with a refrigerator, sink, and cabinetry.

Adorable Cottage with Cottage porch, walk to water & town

8.8 out of 10, Excellent, (6)
"Very nice and comfortable property "
Adorable Cottage with Cottage porch, walk to water & town
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Enjoy a serene beach experience with gentle waves lapping at the shore.

Renovated Milford Beach home by Charles Island/Silver Sands Pk

10.0 out of 10, Exceptional, (6)
"This place was perfection for my mom and I. The location was easy to get to from highway, the inside of the place was spotless, updated and cozy and property owner Susana was highly responsive to any questions we had. The location was ideal for walks both on the beach and on walking paths. We will definitely stay again in the future. "
Renovated Milford Beach home by Charles Island/Silver Sands Pk
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Enjoy cooking in the central island kitchen with stainless steel appliances and ample natural light.

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

10.0 out of 10, Exceptional, (3)
"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!
Charming 3-bedroom cottage in Old Saybrook with AC, WiFi
Enjoy cooking in this well-equipped kitchen with a stove, oven, microwave, and refrigerator.

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

10.0 out of 10, Exceptional, (3)
"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
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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Top Thimble Islands Hotel Reviews

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Close to all the stores"
James 3-night trip
Posted 12 hours ago
Best Western Executive Hotel Of New Haven - West Haven

Frequently asked questions

How much do cottages in Thimble Islands cost?
Prices for cottages in Thimble Islands range between NZ$463 and NZ$900 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 105 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.