Holiday Homes in Thimble Islands

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Find holiday rentals that suit your style

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Thimble Islands holiday homes

A marina with multiple docks and boats, surrounded by residential buildings and greenery.

1. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
8.0 out of 10, Very good, (6 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$390
includes taxes & fees
30 Nov - 1 Dec
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
A living room with a sofa, a coffee table, a TV, and a lamp.

2. 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$765
includes taxes & fees
30 Nov - 1 Dec
Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale
A living room with a staircase, a sofa, a coffee table, and a TV.

3. 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$440
includes taxes & fees
10 Nov - 11 Nov
Loft •Pool • Gym • Free Parking • Near Yale
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

4. 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$542
includes taxes & fees
30 Nov - 1 Dec
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

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

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is NZ$523
includes taxes & fees
12 Nov - 13 Nov
Once the old Schools house now a newly furnished Apartment
A modern kitchen with a stainless steel refrigerator, wooden beams, a dining area with a table and chairs, and a large window with blinds.

6. Coastal Landing Stay

Coastal Landing Stay
East Shore
The price is NZ$868
includes taxes & fees
10 Nov - 11 Nov
Coastal Landing Stay
A spacious living room with a large sectional sofa, a flat-screen TV, and a dining area with a table and chairs.

7. 5BR Short Drive to Yale | 8 Beds | Ping-Pong

5BR Short Drive to Yale | 8 Beds | Ping-Pong
Hamden
The price is NZ$998
includes taxes & fees
29 Nov - 30 Nov
5BR Short Drive to Yale | 8 Beds | Ping-Pong
A modern kitchen with white cabinetry, a central island with stools, pendant lighting, and a view to an outdoor area.

8. 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$1,257
includes taxes & fees
8 Dec - 9 Dec
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
A staircase with dark wooden steps and black balusters, a round mirror on the wall, a blue armchair, a wicker basket with flowers, and a floor lamp.

9. Las Casitas Retreat

Las Casitas Retreat
East Shore
10.0 out of 10, Exceptional, (1 review)
"La Caistas Retreat was a wonderful experience. The place was very clean and cozy. We visited with 2 of my adult children and their significant others and had plenty of room. The host, Sujata, was very informative amd checked in daily. The check-in and out were very smooth. I would recommend this place to anyone visiting New Haven!!!!"
United States
Tim H.
The price is NZ$1,202
includes taxes & fees
10 Nov - 11 Nov
Las Casitas Retreat
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

10. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (4 reviews)
"Very lovely home! We very much enjoyed our stay and hope to be back again!"
United States
Morgan M.
The price is NZ$1,064
includes taxes & fees
1 Dec - 2 Dec
Beachside Bliss w/ Game Room, Gym & Golf Green
A covered porch with a wicker chair and a potted plant.

11. 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, (7 reviews)
"Great stay!"
United States
Mark S.
The price is NZ$710
includes taxes & fees
10 Nov - 11 Nov
3-bedroom house just walking distance from Yale and Downtown
A covered patio with a glass table, white metal chairs, a green sofa, and a white metal bench.

12. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.4 out of 10, Exceptional, (93 reviews)
"The location of this place is best!"
United States
Dr. Maureen C.
The price is NZ$1,088
includes taxes & fees
10 Nov - 11 Nov
Historic New England home ,Reunions Beach pass
Lovely spacious kitchen to cook and enjoy your meals; Large island to sit and eat.

13. Heavenly Home in New Haven /5 mins drive from Yale

Heavenly Home in New Haven /5 mins drive from Yale
Fair Haven
9.2 out of 10, Wonderful, (24 reviews)
"Place was so cute and spacious. Owner was awesome too! Definitely recommend."
United States
Aliza T.
The price is NZ$1,380
includes taxes & fees
22 Nov - 23 Nov
Heavenly Home in New Haven /5 mins drive from Yale
A kitchen counter with a coffee maker, a woven basket, a wine bottle, and a glass.

14. Renovated Beachside Retreat

Renovated Beachside Retreat
Milford
10.0 out of 10, Exceptional, (1 review)
"Terrific place to stay in Milford. Quaint & quiet neighborhood, close to beach and beautiful park near by to walk at (Walnut Beach Park). House was very well kept and stocked with everything you would need. Host communication was thorough and prompt. Would absolutely stay here again."
United States
Michelle D.
The price is NZ$765
includes taxes & fees
12 Nov - 13 Nov
Renovated Beachside Retreat
A wooden deck with a table and chairs, overlooking a river and trees.

15. Steps to Beach • Hot Tub • Game Room • Water Views

Steps to Beach • Hot Tub • Game Room • Water Views
Branford
The price is NZ$2,177
includes taxes & fees
10 Nov - 11 Nov
Steps to Beach • Hot Tub • Game Room • Water Views
A marina with multiple docks and boats, surrounded by a forested area and residential buildings.

16. Gorgeous Waterfront 2:1 - 2 houses in 1 building.

Gorgeous Waterfront 2:1 - 2 houses in 1 building.
Fair Haven
The price is NZ$1,306
includes taxes & fees
23 Nov - 24 Nov
Gorgeous Waterfront 2:1 - 2 houses in 1 building.
A modern living room with hardwood flooring, a leather sofa, a round coffee table, and a wooden side table. There is a dining area with a table and chairs visible in the background.

17. Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is NZ$792
includes taxes & fees
10 Nov - 11 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
A modern kitchen with a marble island, bar stools, and a dining area with a table and chairs.

18. Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!

Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
Milford
9.8 out of 10, Exceptional, (10 reviews)
"Very comfortable modern home, clean, great backyard, pet friendly Host was so accommodating and responsive, personal note at check-in "
United States
Traci F.
The price is NZ$768
includes taxes & fees
11 Nov - 12 Nov
Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
A modern living room with a black leather sofa, a coffee table, and a TV stand. There is a staircase leading to another level.

19. 171 Broadway · Renovated House Steps Away From The Ocean

171 Broadway · Renovated House Steps Away From The Ocean
Milford
8.4 out of 10, Very good, (8 reviews)
"very clean, new and great location! Will book again."
United States
ScottTakacs a.
The price is NZ$697
includes taxes & fees
15 Nov - 16 Nov
171 Broadway · Renovated House Steps Away From The Ocean
A modern living room with a large TV, white cabinetry, and a view of the outdoors.

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

Charming beach home, complete with pool & cozy guest house!
Clinton
9.8 out of 10, Exceptional, (56 reviews)
"Beautiful, open and clean. Perfect for a family stay!"
United States
Juliana A.
The price is NZ$2,396
includes taxes & fees
12 Nov - 13 Nov
Charming beach home, complete with pool & cozy guest house!
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 reviews in Thimble Islands

An outdoor patio with a fire feature, seating, and a building with large windows and a stone facade.
Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven
The Centre

10/10 Excellent

This hotel was flawless - immaculately kept, every facility you could want for, perfect location, great staff and unlike most hotels I’ve experienced they are making a big effort to be environmentally conscious I loved our stay here
Australia
Wade
Reviewed December 13, 2025
Home2 Suites by Hilton East Haven New Haven

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