Default HTG hotel image

Holiday Homes in Thimble Islands

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Thimble Islands holiday homes

1. Charming 1-bedroom in a 6-bedrooms house in New Haven perfect for Yale visitors

Charming 1-bedroom in a 6-bedrooms house in New Haven perfect for Yale visitors
Fair Haven
The price is NZ$224
includes taxes & fees
5 Oct - 6 Oct
Charming 1-bedroom in a 6-bedrooms house in New Haven perfect for Yale visitors

2. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"This apartment was wonderful - clean, well stocked, and cute. Aside from the proximity to the train tracks (although earplugs were thoughtfully provided), the location was great - close to the highway and more importantly Dairy Queen."
United States
Becky P.
The price is NZ$516
includes taxes & fees
27 Sept - 28 Sept
Once the old Schools house now a newly furnished Apartment

3. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
7.6 out of 10, Good, (5 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is NZ$402
includes taxes & fees
28 Sept - 29 Sept
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

4. Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (13 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
The price is NZ$1,032
includes taxes & fees
28 Sept - 29 Sept
Clear LI Sound waterview, Wedding pics, Yale&Beach

5. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is NZ$510
includes taxes & fees
6 Oct - 7 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private

6. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.8 out of 10, Exceptional, (16 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is NZ$543
includes taxes & fees
29 Sept - 30 Sept
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

7. Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale

Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale
Newhallville
The price is NZ$709
includes taxes & fees
30 Sept - 1 Oct
Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale

8. Coastal Landing Stay

Coastal Landing Stay
East Shore
The price is NZ$882
includes taxes & fees
27 Sept - 28 Sept
Coastal Landing Stay

9. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.2 out of 10, Wonderful, (90 reviews)
"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 NZ$1,138
includes taxes & fees
30 Sept - 1 Oct
Historic New England home ,Reunions Beach pass

10. Loft •Pool • Gym • Free Parking • Near Yale

Loft •Pool • Gym • Free Parking • Near Yale
Orange
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. Host was accommodating and quick to respond when we encountered issues."
United States
Ali B.
The price is NZ$466
includes taxes & fees
27 Sept - 28 Sept
Loft •Pool • Gym • Free Parking • Near Yale

11. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is NZ$832
includes taxes & fees
29 Sept - 30 Sept
Adorable Cottage, 5 min walk to water & town

12. Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
East Shore
8.8 out of 10, Excellent, (5 reviews)
"Fantastic place, amazing hosts, 100% recommend! "
United States
Zach P.
The price is NZ$1,267
includes taxes & fees
28 Sept - 29 Sept
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

13. Las Casitas Retreat

Las Casitas Retreat
East Shore
The price is NZ$1,135
includes taxes & fees
28 Sept - 29 Sept
Las Casitas Retreat

14. Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven

Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven
Foxon
10.0 out of 10, Exceptional, (1 review)
"Place looks way better in person, cozy and quiet. Loved the backyard and deck also plenty of fast food restaurants and Walmart near by."
United States
Fateema M.
The price is NZ$795
includes taxes & fees
2 Oct - 3 Oct
Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven

15. Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
Fair Haven
5.6 out of 10, (4 reviews)
"Blankets where itchy and smelled dirty small room when whole house was listed"
United States
Isabella R.
The price is NZ$224
includes taxes & fees
5 Oct - 6 Oct
Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

16. 3-bedroom house just walking distance from Yale and Downtown

3-bedroom house just walking distance from Yale and Downtown
Dixwell
10.0 out of 10, Exceptional, (6 reviews)
"Great stay!"
United States
Mark S.
The price is NZ$795
includes taxes & fees
7 Oct - 8 Oct
3-bedroom house just walking distance from Yale and Downtown

17. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (13 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is NZ$792
includes taxes & fees
27 Sept - 28 Sept
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

18. Renovated Beachside Retreat

Renovated Beachside Retreat
Milford
The price is NZ$628
includes taxes & fees
8 Oct - 9 Oct
Renovated Beachside Retreat
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Thimble Islands Hotel Reviews

Find out more about Thimble Islands

Thimble Islands Holiday Homes information

Number of reviews
195
Accommodation
277 Holiday Homes
Lowest Price
NZ$224
Highest Price
NZ$1,267

Explore a world of travel with Expedia