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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Thimble Islands and around

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.
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 cottage short walk to Chalker Beach
Relax in a comfortable seating area with a sofa and armchairs, perfect for unwinding in front of the large flat-screen TV.

Charming 3-bedroom cottage short walk to Chalker Beach

10.0 out of 10, Exceptional, (2)
"Lovely location very close to Harvey's Beach and local attractions . Home is very well kept in a quiet neighborhood "
Charming 3-bedroom cottage short walk to Chalker 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
Charming Westbrook Cottage, Steps to Private Beach
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and refrigerator.

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
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
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 €259
includes taxes & fees
1 Sept - 2 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
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!
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, (15)
"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
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 €548
includes taxes & fees
4 Aug - 5 Aug
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
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
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
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
1930s Waterfront Cottage on Tuttle's Point
Enjoy cooking in this kitchen with oven and sink, plus ample storage in the cabinets above.

1930s Waterfront Cottage on Tuttle's Point

9.8 out of 10, Exceptional, (27)
"We had a wonderful stay! The kitchen was well outfitted and the beach was perfect for our little grandson. Great kayaking, biking, hiking and of course, eating! Backyard and porch were awesome."
1930s Waterfront Cottage on Tuttle's Point
Beach cottage on private beach!
Enjoy ocean views from the deck with seating and a table.

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!
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

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

10/10 Excellent
"Great location"
Emma 2-night trip
Posted 21 hours ago
Cambria Hotel New Haven University Area

Frequently asked questions

How much do cottages in Thimble Islands cost?
Prices for cottages in Thimble Islands range between €259 and €548 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 108 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.