Search Thimble Islands Cottage Rentals from CA $153

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Thimble Islands cottages

A two-story house with a covered porch, a front door, and a small outdoor seating area with a table and chairs.

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

Cozy Home near private beach , close to New Haven area colleges Hospitals
Branford
9.4 out of 10, Exceptional, (86 reviews)
"Property was clean with some nice cozy touches. Wine on the table, fruit in the frig, chocolate for comfort, coffee for wakeup. Host was very pleasant and accommodating. Will definitely stay there again."
United States
Vincent
The price is CA $154
CA $406 total
includes taxes & fees
Nov 17 - Nov 18
Cozy Home near private beach , close to New Haven area colleges Hospitals
A two-story house with a porch, a mailbox, and a lawn.

2. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is CA $220
CA $468 total
includes taxes & fees
Nov 8 - Nov 9
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

3. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (66 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $185
CA $328 total
includes taxes & fees
Nov 9 - Nov 10
1-bedroom cottage with Grove Beach 🏖️ access.
A kitchen with white cabinets, a black refrigerator, a double sink, and a window overlooking a wooded area.

4. Serene Country Cottage

Serene Country Cottage
Woodbridge
8.0 out of 10, Very good, (11 reviews)
"We had a great one night stay here! The place is really cute, clean and comfortable. One of the greatest parts about the stay was the host, Trent. He was welcoming and VERY responsive to questions! "
United States
felicia
The price is CA $180
CA $291 total
includes taxes & fees
Nov 17 - Nov 18
Serene Country Cottage
A white cottage with a front door, a garage, and a small porch with a potted plant.

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

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (31 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is CA $283
CA $480 total
includes taxes & fees
Nov 7 - Nov 8
The gardners Cottage 1 mile from long Island Sound - pet friendly
A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

6. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is CA $386
CA $520 total
includes taxes & fees
Nov 17 - Nov 18
Westbrook Getaway-Near Beaches, Train & Shoreline
A two-story house with a porch, multiple windows, and a front door.

7. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and comfortable"
United States
Francine F.
The price is CA $341
CA $798 total
includes taxes & fees
Nov 5 - Nov 6
Adorable Cottage with Cottage porch, walk to water & town
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 reviews in Thimble Islands

A modern building entrance with a covered walkway, a white car parked in front, and two people near the entrance.
Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton
Long Wharf

10/10 Excellent

Great stay
Canada
NADA
Reviewed November 1, 2026
Hotel Marcel New Haven, Tapestry Collection By Hilton

Frequently Asked Questions

How much do cottages in Thimble Islands cost?

Prices for cottages in Thimble Islands range between CA $153 and CA $385 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 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.

How can I find cheap cottages in Thimble Islands?

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