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Vacation Homes in Thimble Islands

Stunning Waterfront Home with Private Beach!

10.0 out of 10, Exceptional, (43)
"The property is immaculate, so clean and peaceful, views are stunning. Can’t recommend enough."
Stunning Waterfront Home with Private Beach!

🌾Welcoming Tiny Home! Downtown & Beachy☀️

8.8 out of 10, Excellent, (6)
"The property had a beautiful secluded outdoor space that complemented the tiny home."
🌾Welcoming Tiny Home! Downtown & Beachy☀️

Relax by the River | Branford Waterfront Home

10.0 out of 10, Exceptional, (2)
"Clean, family friendly, and fun."
Relax by the River | Branford Waterfront Home

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (130)
"My husband and I had a wonderful time at this idyllic cottage on the water in Branford. Great location and hosts. Beautiful community for long walks, restaurants nearby. Highly recommend! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

9.8 out of 10, Exceptional, (7)
"5 Star stay!"
The price is AED 1,102
AED 2,132 total
includes taxes & fees
13 Jul - 14 Jul
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

Bright Milford Beach House w/ Outdoor Shower

9.2 out of 10, Wonderful, (10)
"We had the best time! It was clean, good location, and the owner was wonderful! We even got to go the beach in December! We would definitely rent this place again!!"
Bright Milford Beach House w/ Outdoor Shower

Charming beach home, complete with pool & cozy guest house!

9.6 out of 10, Exceptional, (25)
"Wonderful property. Plenty of room for 7 adults. Would definitely stay there again. "
Charming beach home, complete with pool & cozy guest house!

2 Mi to Dtwn: 2-Acre Retreat w/ Large Yard!

10.0 out of 10, Exceptional, (1)
"My family are former Madison residents and were visiting friends over the Holidays. This location was everything we were looking for. Highly recommend. "
2 Mi to Dtwn: 2-Acre Retreat w/ Large Yard!

Updated ranch Home 4 minutes from the beach on a quiet end street.

8.4 out of 10, Very Good, (7)
"It was everything that I expected. Fabian was very attentive and responsive. I would definitely rent again. "
Updated ranch Home 4 minutes from the beach on a quiet end street.

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

2.0 star property
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is AED 657
AED 957 total
includes taxes & fees
11 Jul - 12 Jul
Shoreline Oasis

Dulce La Donna by the beach

Dulce La Donna by the beach

Cozy 3 bedroom minutes from Yale and the beach

Cozy 3 bedroom minutes from Yale and the beach

Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

10.0 out of 10, Exceptional, (56)
"We really enjoyed our stay at the property. The home was very clean, the beds were comfortable, and the location was convenient for all of our weekend activities."
Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

10.0 out of 10, Exceptional, (48)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

The Jewel of The Cove - Historic Coastal Retreat

2.0 star property
10.0 out of 10, Exceptional, (2)
"A group of us stayed there for a work trip and it was the perfect situation for us. The beds were SO comfortable! The decor was vibe! Supplies were plenty. Towels were top quality. The fire pit was so fun to use on our last night in town. Very close to a beach so we could dip our toes in the ocean.There is an airport runway behind the property but the noise wasn’t terrible. "
The price is AED 859
AED 2,005 total
includes taxes & fees
29 Jun - 30 Jun
The Jewel of The Cove - Historic Coastal Retreat

Direct Waterfront Private Beach Escape

9.8 out of 10, Exceptional, (13)
"The house was great! Beautiful ocean front property with beachy vibes all throughout the neighborhood and interior of the home. The host was extremely clear on directions and provided amazing instructions. Very comfortable stay! "
Direct Waterfront Private Beach Escape

Heavenly Home in New Haven /5 mins drive from Yale

8.8 out of 10, Excellent, (18)
"The property was prepared well and we enjoyed our stay. Thanks"
The price is AED 3,239
AED 4,459 total
includes taxes & fees
22 Jun - 23 Jun
Heavenly Home in New Haven /5 mins drive from Yale

McAngel Haven: 5 mins from Yale

9.8 out of 10, Exceptional, (10)
"Had a wonderful but short stay in New Haven. Home.of PEZ and PIZZA . "
The price is AED 843
AED 1,935 total
includes taxes & fees
18 Jun - 19 Jun
McAngel Haven: 5 mins from Yale

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (14)
"perfect location beautiful house"
The price is AED 1,983
AED 2,850 total
includes taxes & fees
22 Jun - 23 Jun
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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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