Search Vacation Homes in Thimble Islands

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Thimble Islands holiday homes

Fridge, microwave, oven, stovetop
Adorable Cottage, 5 min walk to water & town

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$1,352
HK$3,246 total
includes taxes & fees
28 Dec - 29 Dec
Adorable Cottage, 5 min walk to water & town
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Holiday Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
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
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Holiday Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
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$1,052
HK$3,895 total
includes taxes & fees
7 Jan - 8 Jan 2026
Beachside Bliss w/ Game Room, Gym & Golf Green
Microwave, oven, stovetop, dishwasher
Cozy East Haven Home • Near Beach & Yale

Holiday Home in Momauguin

Cozy East Haven Home • Near Beach & Yale
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! "
United States
Amal A.
The price is HK$875
HK$1,162 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy East Haven Home • Near Beach & Yale
Private kitchen
Stylish Modern Stay Steps from the Ocean

Holiday Home in Clinton

Stylish Modern Stay Steps from the Ocean
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$1,400
HK$2,799 total
includes taxes & fees
28 Dec - 29 Dec
Stylish Modern Stay Steps from the Ocean
Terrace/patio
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Holiday Home in Saybrook Manor

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
9.6 out of 10, Exceptional, (133)
"We loved our stay!"
United States
Deana L.
The price is HK$1,944
HK$4,498 total
includes taxes & fees
12 Jan - 13 Jan 2026
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Outdoor dining
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking

Holiday Home in East Rock

Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking
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$2,757 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking
TV
Newly Remodeled 1-BR Close to Everything yet Very Private

Holiday Home in Wallingford

Newly Remodeled 1-BR Close to Everything yet Very Private
10.0 out of 10, Exceptional, (9)
"The flat has a nice layout and was very comfortable. We enjoyed our stay."
United States
Mary R.
The price is HK$894
HK$2,241 total
includes taxes & fees
1 Jan - 2 Jan 2026
Newly Remodeled 1-BR Close to Everything yet Very Private
Fridge, microwave, oven, coffee/tea maker
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Holiday Home in Fair Haven

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
7.6 out of 10, Good, (5)
"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 HK$995
HK$1,907 total
includes taxes & fees
29 Dec - 30 Dec
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fridge, microwave, oven, stovetop
LONG-TERM Winter by the Ocean and Ski Resort 30 mins away

Holiday Home in Clinton

LONG-TERM Winter by the Ocean and Ski Resort 30 mins away
2.0 star property
10.0 out of 10, Exceptional, (3)
"Vincent was amazing to work with! We decided to change the dates and he was very patient and helpful while we got it updated with VRBO. The home is in a peaceful neighborhood with beautiful trees and active squirrels (my daughter’s favorite part). The location was convenient for our needs. We all enjoyed the game tables and the convenience of the washer and dryer. We even tried out the projector one night to watch a couple of episodes of Gilmore Girls – so fun! Vincent checked in once we arrived...
United States
Erin S.
The price is HK$1,162
HK$4,231 total
includes taxes & fees
4 Jan - 5 Jan 2026
LONG-TERM Winter by the Ocean and Ski Resort 30 mins away
Fridge, microwave, oven, stovetop
Stocked home close to Yale, in Heart of New Haven

Holiday Home in Mill River

Stocked home close to Yale, in Heart of New Haven
9.2 out of 10, Wonderful, (18)
"Great value very close to university. "
United States
Lawrence
The price is HK$980
HK$1,720 total
includes taxes & fees
28 Dec - 29 Dec
Stocked home close to Yale, in Heart of New Haven
Interior
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Holiday Home in Fair Haven

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
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$2,579 total
includes taxes & fees
29 Dec - 30 Dec
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Dining tables
The ARLO - Walk to Brewery and Restaurants

Holiday Home in Milford

The ARLO - Walk to Brewery and Restaurants
9.4 out of 10, Exceptional, (3)
"Very nice house....loved the front enclosed porch, and the kitchen was amazing with everything we needed. The deck with the Blackstone Grill was a great place to sit and relax. We enjoyed many of the nearby restaurants too. Matt and Jess were great hosts!J&J, Mooresville, NC"
United States
Jena
The price is HK$1,050
HK$2,867 total
includes taxes & fees
29 Dec - 30 Dec
The ARLO - Walk to Brewery and Restaurants
Exterior detail
The Santiago in Science Park at Yale New Haven

Holiday Home in Dixwell

The Santiago in Science Park at Yale New Haven
8.0 out of 10, Very good, (8)
"The property had everything needed and was a short distance to so many campus sites. Would definitely stay again."
United States
Natalie B.
The Santiago in Science Park at Yale New Haven
Private kitchen
Cozy 2-bedroom house in amazing New Haven

Holiday Home in Quinnipiac Meadows

Cozy 2-bedroom house in amazing New Haven
2.0 star property
The price is HK$1,431
HK$2,357 total
includes taxes & fees
8 Jan - 9 Jan 2026
Cozy 2-bedroom house in amazing New Haven
Terrace/patio
The Jewel of The Cove - Historic Coastal Retreat

Holiday Home in East Shore

The Jewel of The Cove - Historic Coastal Retreat
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$1,610
HK$3,989 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Jewel of The Cove - Historic Coastal Retreat
Fridge, microwave, oven, stovetop
Casa Soleada in East Rock |King Bed| Near DT and Yale SOM | Free parking

Holiday Home in East Rock

Casa Soleada in East Rock |King Bed| Near DT and Yale SOM | Free parking
9.8 out of 10, Exceptional, (10)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
Australia
Nina
The price is HK$1,431
HK$3,142 total
includes taxes & fees
28 Dec - 29 Dec
Casa Soleada in East Rock |King Bed| Near DT and Yale SOM | Free parking
Fridge, microwave, oven, stovetop
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Holiday Home in Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
2.0 star property
The price is HK$711
HK$3,010 total
includes taxes & fees
9 Jan - 10 Jan 2026
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Fridge, microwave, oven, stovetop
Historic New England home ,Reunions Beach pass

Holiday Home in Guilford

Historic New England home ,Reunions Beach pass
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$2,099
HK$4,176 total
includes taxes & fees
1 Jan - 2 Jan 2026
Historic New England home ,Reunions Beach pass
Private kitchen
3-bedroom townhome in peaceful New Haven near Yale Science Center

Holiday Home in Dixwell

3-bedroom townhome in peaceful New Haven near Yale Science Center
2.0 star property
The price is HK$1,773
HK$2,288 total
includes taxes & fees
8 Jan - 9 Jan 2026
3-bedroom townhome in peaceful New Haven near Yale Science Center
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Thimble Islands Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Location is beautiful! Rooms are very nice and the staff are very helpful "
Lisa 1-night trip
Posted 1 day ago
Water's Edge Resort & Spa

Find out more about Thimble Islands

Thimble Islands Vacation Homes information

Number of reviews
230
Accommodation
313 Vacation Homes
Lowest Price
HK$1,162
Highest Price
HK$4,498

Explore a world of travel with Expedia