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Compare 280 Vacation Homes in Thimble Islands with updated reviews, rates, and availability.

Cozy dog friendly updated house in quiet village adjacent to park

10.0 out of 10, Exceptional, (24)
"We stayed here for 3 weeks while waiting for our home to be ready, and it was a wonderful stay. The house is so comfy, beautiful park and trails, and the backyard is loads of fun. Amazing host who responds immediately and is very kind. 100% recommend!"
Cozy dog friendly updated house in quiet village adjacent to park

Room in Apartment - Plaid Room 3min From Yale Univ

3.0 star property
10.0 out of 10, Exceptional, (1)
"The owner is great and made great accommodations for our stay, the price was wonderful. The neighborhood maybe wasent the nicest but thats kinda out of his control."
Room in Apartment - Plaid Room 3min From Yale Univ

The Santiago in Science Park at Yale New Haven

8.0 out of 10, Very Good, (5)
"The property had everything needed and was a short distance to so many campus sites. Would definitely stay again."
The price is AED 367
AED 661 total
includes taxes & fees
3 Feb - 4 Feb
The Santiago in Science Park at Yale New Haven

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (11)
"We enjoyed our beach getaway at the perfect beach side house! The accommodations were very comfortable & clean. The house had everything you’d need with a beautiful view of the water from the kitchen & patio. We had a great time & would love to come back again! "
Cozy Westbrook Vacation Rental - Walk to Beach!

McAngel Haven: 5 mins from Yale

9.8 out of 10, Exceptional, (9)
"Excellent to had a nice house like that "
The price is AED 937
AED 2,082 total
includes taxes & fees
12 Jan - 13 Jan
McAngel Haven: 5 mins from Yale

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

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

Nature's Paradise: Private Dock & Water Views

9.6 out of 10, Exceptional, (8)
"Everything was great"
Nature's Paradise: Private Dock & Water Views

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 with Game Room

The price is AED 1,969
AED 4,205 total
includes taxes & fees
19 Jan - 20 Jan
Near Yale with Game Room

Walk to Beaches: Sunny East Haven Home w/ Grill

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. "
Walk to Beaches: Sunny East Haven Home w/ Grill

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!

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

10.0 out of 10, Exceptional, (128)
"Although I went went it is cold the view and location were excellant. I can definately see taking advantage of this place during the summer. The host was responsive and available. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

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

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (24)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (4)
"Robert was an amazing host..We had an incredible New Year’s Eve…We are already planning our next trip back… "
The price is AED 1,950
AED 3,593 total
includes taxes & fees
1 Feb - 2 Feb
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

adorable ranch in beach community

10.0 out of 10, Exceptional, (44)
"Beautiful location, lovely neighbors. House is dated as seen in photos. "
The price is AED 643
AED 1,538 total
includes taxes & fees
31 Jan - 1 Feb
adorable ranch in beach community

Direct Waterfront Private Beach Escape

9.8 out of 10, Exceptional, (12)
"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

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

9.6 out of 10, Exceptional, (23)
"Wonderful property. Plenty of room for 7 adults. Would definitely stay there again. "
Charming beach home, complete with pool & cozy guest house!

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

10.0 out of 10, Exceptional, (9)
"My friends and I have stayed twice now at this house and have had the best time both times! It has everything we could need in the house and we can’t wait to be back again!"
The price is AED 2,204
AED 3,133 total
includes taxes & fees
12 Jan - 13 Jan
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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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 AED 364
AED 418 total
includes taxes & fees
19 Jan - 20 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 AED 793
AED 1,846 total
includes taxes & fees
12 Jan - 13 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.