Holiday Homes in Thimble Islands

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Featured Holiday Homes in Thimble Islands

Charming cottage by the sea

9.8 out of 10, Exceptional, (9)
"The setting is spectacular! Gorgeous sunrises every morning -set right on the water's edge. Host is very helpful, accommodating, and communication was wonderful. Charming home with great selection of books and games. "
Charming cottage by the sea

Family Gem on Dyer Street

10.0 out of 10, Exceptional, (2)
"Needed a place to stay for the night and it was just the perfect spot. The house was just as it seemed online and it was a lot bigger than I expected. Everything was really nice and the host was super nice and very easy to communicate with. Would 100% recommend to others for their next stay."
Family Gem on Dyer Street

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (85)
"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Waterfront Beach House

9.6 out of 10, Exceptional, (40)
"This was perfect for us. We had a family funeral and this was a nice retreat. We would stay again for sure. "
Waterfront Beach House

Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️

10.0 out of 10, Exceptional, (31)
"Heather’s home was the perfect stay for my son and daughter-in-law and my 2 granddaughters. Her home is sparkling clean and beautifully decorated with a relaxed beach theme. My grandchildren were so to stay there, that they asked when they could come back and stay again. "
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️

Bright Milford Beach House w/ Outdoor Shower

10.0 out of 10, Exceptional, (5)
"Cute place right across from the beach. Had everything that you need to cook, even a vegetable garden with fresh tomatoes. Comfortable and clean. The beach access is across the street,. "
Bright Milford Beach House w/ Outdoor Shower

Coastal Bungalow Sanctuary, Game Room, Ocean Views

8.8 out of 10, Excellent, (11)
"The house was clean and the just was very nice‼️"
The price is AU$618
includes taxes & fees
9 Dec - 10 Dec
Coastal Bungalow Sanctuary, Game Room, Ocean Views

Home on the sound

8.6 out of 10, Excellent, (7)
"This was a greay stay and the property was really cute and cozy. It is an upstairs portion of a duplex "
Home on the sound

Walkable New Haven Retreat w/ Ocean Views!

9.6 out of 10, Exceptional, (22)
"We had a great time. Location was perfect and the staff was super responsive and flexible."
Walkable New Haven Retreat w/ Ocean Views!

Enjoy a taste of New England in Historic Guilford Ct

10.0 out of 10, Exceptional, (9)
"Wonderful property combining original details with modern amenities. Well located near the town green and shops. We would definitely stay here again."
Enjoy a taste of New England in Historic Guilford Ct

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (8)
"Host worked with me due to larger dog. Very accurate instructions and all amenities were very good. Will stay here again"
Ranch style living at its best with country garden & patio!

Near Yale 8 beds Gaming Room

The price is AU$1,677
includes taxes & fees
1 Jan - 2 Jan 2025
Near Yale 8 beds Gaming Room

Sunny, Beach Days - Enjoy the beach just steps away in Clinton, Connecticut

8.0 out of 10, Very good, (1)
"It was a great location and time spent with friends! "
Sunny, Beach Days - Enjoy the beach just steps away in Clinton, Connecticut

Luxe Lake House in Connecticut

The price is AU$1,429
includes taxes & fees
3 Dec - 4 Dec
Luxe Lake House in Connecticut

Sunny East Haven Home w/ Grill: Walk to Beaches!

2.0 star property
10.0 out of 10, Exceptional, (3)
"6 of us stayed here for a music festival. The location, fantastic! Ocean views, check. The bedding, the furniture, kitchen supplies....no amenity was overlooked. Happened to meet owner when were checking in. He was great. Couldn't have been more accomodating. Great great place for a few nights or longer. Wush we were here longer. "
Sunny East Haven Home w/ Grill: Walk to Beaches!

Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!

2.0 star property
10.0 out of 10, Exceptional, (6)
"We had an absolute fantastic time staying at this place. My son was got married at the Beech Tree Cottages (also was the perfect wedding venue) in Madison, Ct. about 15 minutes from the house which worked out perfectly for staying here. From start to finish, everything exceeded our expectations. The communication with Chase was smooth and prompt, making the booking process hassle free. Upon our arrival we were greeted with a welcome gift. The space was clean, modern and beautifully...
Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (26)
"When my hometown sib couldn't host, we rented here and had our family Thanksgiving! It was great!"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (26)
"Wonderful little bungalow. Owners are really nice and responsive. House is well maintained, cleaned and better stocked than any other rental we've been in. Thank you!!"
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (58)
"Great"
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (69)
"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "
Beautiful 4BR Beach House with Private Beach Access.
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, (1973)
"Convenient location, helpful staff, comfortable bed. Thanks!"
The price is AU$175
includes taxes & fees
8 Dec - 9 Dec
New Haven Village Suites

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

9.8 out of 10, Exceptional, (103)
"We enjoyed or stay very much! It was quiet and the easy walk to the water was great. Not much in the way of a beach but still the view is lovely. The Master Bed needs updating. Husband and I sank into the middle squishing together. The living room slipcovers could use a wash and some bleach. The backyard is a great value added but the railing on the porch needs repair. "
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.