Holiday Homes in Thimble Islands
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Our top choices for Thimble Islands holiday homes
Adorable Cottage, 5 min walk to water & town
Adorable Cottage, 5 min walk to water & townWestbrook Center
9.4 out of 10, Exceptional, (15)
"Very nice small place to stay by the beach and close to great coffee shop. "
Donovan V.
The price is NZ$715
includes taxes & fees
28 Dec - 29 Dec
Once the old Schools house now a newly furnished Apartment
Once the old Schools house now a newly furnished ApartmentWallingford Center
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
Jeanette W.
The price is NZ$494
includes taxes & fees
2 Jan - 3 Jan 2026
Beachside Bliss w/ Game Room, Gym & Golf Green
Beachside Bliss w/ Game Room, Gym & Golf GreenWestbrook
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
Shannon G.
The price is NZ$863
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy East Haven Home • Near Beach & Yale
Cozy East Haven Home • Near Beach & YaleMomauguin
10.0 out of 10, Exceptional, (4)
"Such a cute place, loved all the nautical touches. Great space for a weekend getaway, pretty well-stocked kitchen, clean & cozy. Really appreciated the outdoor space & amenities too! And Michael the host is very responsive & helpful! "
Amal A.
The price is NZ$256
includes taxes & fees
4 Jan - 5 Jan 2026
Stylish Modern Stay Steps from the Ocean
Stylish Modern Stay Steps from the OceanClinton
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. "
Kelly Z.
The price is NZ$617
includes taxes & fees
31 Dec - 1 Jan 2026
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent YardSaybrook Manor
9.6 out of 10, Exceptional, (133)
"We loved our stay!"
Deana L.
The price is NZ$991
includes taxes & fees
12 Jan - 13 Jan 2026
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free ParkingEast Rock
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"
Derek L.
The price is NZ$608
includes taxes & fees
5 Jan - 6 Jan 2026
Newly Remodeled 1-BR Close to Everything yet Very Private
Newly Remodeled 1-BR Close to Everything yet Very PrivateWallingford
10.0 out of 10, Exceptional, (9)
"The flat has a nice layout and was very comfortable. We enjoyed our stay."
Mary R.
The price is NZ$494
includes taxes & fees
1 Jan - 2 Jan 2026
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
Hampton Inn by Hilton Shelton
10/10 Excellent
Find out more about Thimble Islands
Thimble Islands Holiday Homes information
Number of reviews | 230 |
|---|---|
Accommodation | 313 Holiday Homes |
Lowest Price | NZ$256 |
Highest Price | NZ$991 |
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