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)
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)
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)
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)
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)
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)
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)
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 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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