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Compare 83 Cottages in Thimble Islands with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (59)
"The hosts were great - very responsive. Location was convenient. The cottage is a little quirky in its layout, but we enjoyed our stay. "
Cozy Home near private beach , close to New Haven area colleges Hospitals

Beach Bungalow, large porch, 1/2 mile to the water.

8.4 out of 10, Very Good, (5)
"Very nice and comfortable property "
Beach Bungalow, large porch, 1/2 mile to the water.

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.0 out of 10, Wonderful, (20)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is SAR 409
SAR 718 total
includes taxes & fees
13 Jan - 14 Jan
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (89)
"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

Historic Whitneyville Cottage

9.4 out of 10, Exceptional, (13)
"Road noise was annoying. Otherwise as advertised."
Historic Whitneyville Cottage

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (106)
"Wonderful place to spend time with the family in this cozy cottage. Would love to come back in the summer to enjoy the beach. "
The price is SAR 811
SAR 1,887 total
includes taxes & fees
13 Jan - 14 Jan
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

9.8 out of 10, Exceptional, (26)
"Beautiful place, clean , enjoyable beachside"
Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

Short Beach Coastal Cottage

10.0 out of 10, Exceptional, (14)
"It was really evident that the hosts enjoy this project. Very nice people and everything was tip top."
Short Beach Coastal Cottage

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

10.0 out of 10, Exceptional, (2)
"This was an amazing place to stay. Beautiful property and EXCELLENT hosts! Thank you!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

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!

The Dream Location for Your Perfect Vacation

9.8 out of 10, Exceptional, (16)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation

Guilford Carriage House at Granite Lodge!

10.0 out of 10, Exceptional, (8)
"We had a couple of out of town events in the are this past weekend, and it was also my birthday, so we decided to stay somplace special. The Granite Lodge Carriage hose was all of that! Beautifully decorated and furnished with lots of special touches from the host! We would definitely recommend, and will!"
Guilford Carriage House at Granite Lodge!

Waterfront Cottage w/ Sunroom + Patio & Grill

8.0 out of 10, Very Good, (5)
"Overall it was a nice relaxing stay. Nice and clean. Lots of sun through the back windows. Amenities were much appreciated, in kitchen, bathroom and bedrooms."
Waterfront Cottage w/ Sunroom + Patio & Grill

Renovated Milford Beach home by Charles Island/Silver Sands Pk

10.0 out of 10, Exceptional, (4)
"Our family of 4 stayed comfortably. Towels and sheets were well stocked. We loved walking across to the beach. Our 10 year old could take our 5 year old. We biked on street and sidewalks to downtown Milford, public library, playground. We loved Pennys used books. It was such a relaxing trip and we will be back to stay at Susana's lovely place."
Renovated Milford Beach home by Charles Island/Silver Sands Pk

DIRECT WATERFRONT PRIVATE BEACH

9.4 out of 10, Exceptional, (23)
"I picked this rental because I recognized it as soon as I saw it! I grew up 5 houses from here. The rental was immaculate, the beach beautiful….home. Owners were very nice and helpful. They say you can’t go home again but I got pretty close! Fantastic spot. I’ll be back!"
DIRECT WATERFRONT PRIVATE BEACH

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (70)
"Relaxing "
Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook

10.0 out of 10, Exceptional, (60)
"Our 2nd time to stay at this cozy little cottage. We always enjoy our time spent here. And we do enjoy the homemade banana bread."
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook

The Perfect Family Beachfront Cottage The Viola Cottage

10.0 out of 10, Exceptional, (34)
"A fantastic visit! The cottage was so cute, quiet and right on the beach. Karl was an excellent host and so easy to work with. We will most definitely be back!!"
The Perfect Family Beachfront Cottage The Viola Cottage

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

10.0 out of 10, Exceptional, (13)
"The cottage is cozy and clean. It has everything I need. and perfect for me and my dogs. We enjoyed our stay and had a nice winter break. We hope to come back next year. Thank you, Robin!"
The gardners Cottage 1 mile from long Island Sound - pet friendly

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

8.0 out of 10, Very Good, (3)
"Terrific location. 1 block from the beach."
'Grandma's Cottage' w/ Sunroom: Walk to 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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Other property types in Thimble Islands

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (1991)
"One of our favorites"
The price is SAR 372
SAR 427 total
includes taxes & fees
22 Jan - 23 Jan
New Haven Village Suites

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (106)
"Wonderful place to spend time with the family in this cozy cottage. Would love to come back in the summer to enjoy the beach. "
The price is SAR 811
SAR 1,887 total
includes taxes & fees
13 Jan - 14 Jan
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
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.

Frequently asked questions

How much do cottages in Thimble Islands cost?
Cottages in Thimble Islands range between SAR 409 and SAR 811 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. 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?
You can choose from 83 cottages in Thimble Islands. No matter if you’re vacationing with the family or planning a getaway with close friends, Expedia can help you find the right place to enjoy nature’s beauty.
Why book your cottage in Thimble Islands with Expedia?
Reserving a cottage in Thimble Islands is as easy as entering your travel dates and selecting an ideal place for a vacation in the outdoors. From luxurious retreats to budget-friendly properties and cottages that offer perks like a hot tub, Expedia has something for all styles and tastes. As for unbeatable deals? We’ve got them as well!
How can I find cheap cottages in Thimble Islands?
With Expedia’s handy filter tool, scoring cheap cottages in Thimble Islands has never been simpler. To find accommodations that’ll make your bank balance smile, refine your search by amenities, star rating and budget.