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Browse Select Thimble Islands Holiday Homes

Stunning Waterfront Home with Private Beach!

10.0 out of 10, Exceptional, (45)
"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☀️

9.0 out of 10, Wonderful, (7)
"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

8.8 out of 10, Excellent, (3)
"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, (131)
"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

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (3)
"This house was perfect for our visit. It was clean and comfortable and provided everything we needed. Walking distance to a restaurant, coffee shop and the best ice cream! Would definitely stay here again. "
Minutes to Walnut Beach, newly renovated 3 bedroom home

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

9.8 out of 10, Exceptional, (8)
"5 Star stay!"
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!

9.8 out of 10, Exceptional, (26)
"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, (2)
"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 £194
includes taxes & fees
29 Jun - 30 Jun
Shoreline Oasis

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

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (6)
"Property manager was very attentive to our needs and replied to all msgs in a very timely fashion. There were a couple things that needed tending to when we arrived and he took care of it immediately. Despite having parking on the street, it was never an issue and often got the spot that was right next to the house. The beach was directly across the street and was clean with friendly neighbors! Although there is a sign stating no dogs or animals allowed on the beach, there were many dogs on the...
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Cozy 3 bedroom minutes from Yale and the beach

Cozy 3 bedroom minutes from Yale and the beach

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

10.0 out of 10, Exceptional, (48)
"Property was great. Host was very accommodating and great with communicating."
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

New England Beach House ~ Just Steps To The Beach ~ Perfect Getaway!

9.8 out of 10, Exceptional, (26)
" Very nice property. Mary is great to work with. "
New England Beach House ~ Just Steps To The Beach ~ Perfect Getaway!

Cozy Modern Home

9.6 out of 10, Exceptional, (33)
"If you want a quick getaway with friends and family to cool down and relax, or to do a get together and visit nearby attractions, this place is for you. Plenty of space in and out the house, nice and clean, and the beds are pretty comfortable. Over all a great place and will definitely visit again!"
Cozy Modern Home

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 £473
includes taxes & fees
21 Jul - 22 Jul
The Jewel of The Cove - Historic Coastal Retreat

Dulce La Donna by the beach

Dulce La Donna by the 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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