Search Vacation Homes in Thimble Islands

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Our top choices for Thimble Islands holiday homes

2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$727
HK$3,434 total
includes taxes & fees
5 Jan - 6 Jan 2026
Beachside Bliss w/ Game Room, Gym & Golf Green

Holiday Home in Westbrook Center

Adorable Cottage, 5 min walk to water & town
9.4 out of 10, Exceptional, (15)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is HK$1,351
HK$3,236 total
includes taxes & fees
31 Dec - 1 Jan 2026
Adorable Cottage, 5 min walk to water & town
10.0 out of 10, Exceptional, (10)
"My husband and I enjoyed our stay. The host was very easy to communicate with and very responsive. The property is clean and lovely. Gorgeous view. "
United States
Kerri F.
The price is HK$4,469
HK$7,666 total
includes taxes & fees
31 Dec - 1 Jan 2026
Clear LI Sound waterview, Wedding pics, Yale&Beach
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$894
HK$2,241 total
includes taxes & fees
2 Jan - 3 Jan 2026
Once the old Schools house now a newly furnished Apartment
10.0 out of 10, Exceptional, (3)
"Wonderful beach house. We loved staying here! The house is a historic gem and the accommodations were perfect. We enjoyed fabulous fireworks on the deck and walking the beach each morning. We can’t wait to go back. "
United States
Jane S.
The price is HK$2,752
HK$5,528 total
includes taxes & fees
6 Jan - 7 Jan 2026
Spacious 4-bedroom house with WiFi and AC in awesome Milford
2.0 star property
10.0 out of 10, Exceptional, (6)
"loved it so much, beautiful property 100 % would stay again "
United States
Leilani R.
The price is HK$1,609
HK$3,988 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Jewel of The Cove - Historic Coastal Retreat
9.6 out of 10, Exceptional, (133)
"We loved our stay!"
United States
Deana L.
The price is HK$1,944
HK$4,497 total
includes taxes & fees
12 Jan - 13 Jan 2026
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
10.0 out of 10, Exceptional, (24)
"As advertised. Enjoyed our stay. "
United States
Jeff C.
The price is HK$4,548
HK$7,387 total
includes taxes & fees
1 Jan - 2 Jan 2026
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
8.0 out of 10, Very good, (2)
"It was a nice place. We were in CT for a wedding. It was very close to the venue. The bathrooms were a good size for 10 people staying there getting ready. I would definitely return for another family event in the area. Thank you to the home owners."
United States
Suzanne S.
The price is HK$2,918
HK$5,143 total
includes taxes & fees
4 Jan - 5 Jan 2026
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

Holiday Home in West Haven

McAngel Haven: 5 mins from Yale
9.6 out of 10, Exceptional, (18)
"Yhe gouse was very clean and the location was great for our visit to University of New Haven."
United States
Ann Marie S.
The price is HK$1,784
HK$4,065 total
includes taxes & fees
1 Jan - 2 Jan 2026
McAngel Haven: 5 mins from Yale
9.2 out of 10, Wonderful, (23)
"This house has everything you need to enjoy a getaway. Clean, It will sleep 20 and their is room for 20 to gather."
United States
Kathy B.
The price is HK$4,823
HK$6,191 total
includes taxes & fees
4 Jan - 5 Jan 2026
Heavenly Home in New Haven /5 mins drive from Yale
10.0 out of 10, Exceptional, (1)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is HK$1,399
HK$2,799 total
includes taxes & fees
3 Jan - 4 Jan 2026
Stylish Modern Stay Steps from the Ocean
2.0 star property
10.0 out of 10, Exceptional, (3)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is HK$1,084
HK$4,024 total
includes taxes & fees
11 Jan - 12 Jan 2026
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
9.6 out of 10, Exceptional, (14)
"Had a really nice stay, enjoyed this open airy space with comfortable beds and beautiful light with a view of the river. Very nice time, would stay again."
United States
Brian B.
The price is HK$1,384
HK$2,563 total
includes taxes & fees
1 Jan - 2 Jan 2026
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
9.2 out of 10, Wonderful, (90)
"This is a great location, walking distance to the green and other sites. It also worked well for our girls trip of 4 women."
United States
Liz H.
The price is HK$2,098
HK$4,173 total
includes taxes & fees
4 Jan - 5 Jan 2026
Historic New England home ,Reunions Beach pass
9.6 out of 10, Exceptional, (8)
"Property owner takes great care of the place. Instructions were easy to follow and the location was right down the road from the places we were going to. We would rent again if we ever come back to New Haven"
United States
Derek L.
The price is HK$1,026
HK$2,756 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking
9.0 out of 10, Wonderful, (8)
"the apartment was so beautiful, clean, and spacious! it was a great area to be in! the beds were SUPER comfortable as well, highlight of my trip!"
United States
milly s.
The price is HK$1,119
HK$2,915 total
includes taxes & fees
4 Jan - 5 Jan 2026
Orange Oasis in East Rock |Free Parking| Near Yale and DT|Large Memory Foam Beds
2.0 star property
The price is HK$1,779
HK$3,305 total
includes taxes & fees
12 Jan - 13 Jan 2026
Welcoming 4-bedroom house in charming Hamden
9.6 out of 10, Exceptional, (5)
"We recommend this house and would defintely come again. Thank you for a lovely stay."
United States
Mary Lynn S.
Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!

Holiday Home in Quinnipiac Meadows

Cozy 2-bedroom house in amazing New Haven
2.0 star property
The price is HK$1,430
HK$2,355 total
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy 2-bedroom house in amazing New Haven
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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Top Thimble Islands Hotel Reviews

Find out more about Thimble Islands

Thimble Islands Vacation Homes information

Number of reviews
269
Accommodation
313 Vacation Homes
Lowest Price
HK$2,241
Highest Price
HK$7,666

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