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Our top choices for Thimble Islands holiday homes

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$1,120
HK$3,969 total
includes taxes & fees
14 Apr - 15 Apr
Beachside Bliss w/ Game Room, Gym & Golf Green

Cozy Room in charming New Haven near Yale/Hospitals!

Cozy Room in charming New Haven near Yale/Hospitals!
The Hill
9.4 out of 10, Exceptional, (3 reviews)
"Very nice house and very clean I really love it "
United States
Peterson
The price is HK$564
HK$1,210 total
includes taxes & fees
10 Apr - 11 Apr
Cozy Room in charming New Haven near Yale/Hospitals!

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1 review)
"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$940
HK$2,224 total
includes taxes & fees
26 Apr - 27 Apr
Stylish Modern Stay Steps from the Ocean

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (136 reviews)
"This house was in a great location for our extended family Christmas gathering in Deep River. There was more than enough room for 3 adult couples and 2 older children tonstay comfortably & enjoy a cosy fire in fireplace one evening. "
United States
Karen B.
The price is HK$1,974
HK$4,525 total
includes taxes & fees
12 Apr - 13 Apr
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

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, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$901
HK$2,250 total
includes taxes & fees
10 May - 11 May
Once the old Schools house now a newly furnished Apartment

Stocked home close to Yale, in Heart of New Haven

Stocked home close to Yale, in Heart of New Haven
Mill River
9.2 out of 10, Wonderful, (20 reviews)
"Great value very close to university. "
United States
Lawrence
The price is HK$987
HK$1,733 total
includes taxes & fees
14 Apr - 15 Apr
Stocked home close to Yale, in Heart of New Haven

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 HK$1,003
HK$1,858 total
includes taxes & fees
14 Apr - 15 Apr
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

The Jewel of The Cove - Historic Coastal Retreat

The Jewel of The Cove - Historic Coastal Retreat
East Shore
9.8 out of 10, Exceptional, (7 reviews)
"This was a great place to stay in New Haven, and a lot of care has gone into making it a welcoming house."
United States
Geoffrey H.
The price is HK$1,621
HK$4,018 total
includes taxes & fees
20 Apr - 21 Apr
The Jewel of The Cove - Historic Coastal Retreat

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is HK$1,324
HK$2,486 total
includes taxes & fees
4 May - 5 May
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Welcoming 4-bedroom house in charming Hamden

Welcoming 4-bedroom house in charming Hamden
Hamden
10.0 out of 10, Exceptional, (1 review)
"Host was kind and attentive. Location was convenient and the home was clean and spacious. "
United States
Renee H.
The price is HK$2,115
HK$3,701 total
includes taxes & fees
14 Apr - 15 Apr
Welcoming 4-bedroom house in charming Hamden

McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale
West Haven
9.6 out of 10, Exceptional, (20 reviews)
"Excellent location Clean and spacious Comfortable beds "
United States
Joseph T.
The price is HK$1,797
HK$4,096 total
includes taxes & fees
12 Apr - 13 Apr
McAngel Haven: 5 mins from Yale

Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (11 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
The price is HK$4,504
HK$7,695 total
includes taxes & fees
17 Apr - 18 Apr
Clear LI Sound waterview, Wedding pics, Yale&Beach

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, (23 reviews)
"This house has everything you need to enjoy a getaway. Clean, It will sleep 20 and their is room for 20 to gather."
United States
Kathy B.
The price is HK$3,771
HK$4,822 total
includes taxes & fees
14 Apr - 15 Apr
Heavenly Home in New Haven /5 mins drive from Yale

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, (3 reviews)
"Fantastic place, amazing hosts, 100% recommend! "
United States
Zach P.
The price is HK$2,285
HK$4,313 total
includes taxes & fees
22 Apr - 23 Apr
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

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 HK$1,010
HK$3,431 total
includes taxes & fees
13 Apr - 14 Apr
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Expansive New Haven Home | Near Yale University

Expansive New Haven Home | Near Yale University
West New Haven
The price is HK$2,145
HK$5,147 total
includes taxes & fees
13 Apr - 14 Apr
Expansive New Haven Home | Near Yale University

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
9.8 out of 10, Exceptional, (26 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is HK$4,699
HK$7,570 total
includes taxes & fees
14 Apr - 15 Apr
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

The Coastal Landing Stay

The Coastal Landing Stay
East Shore
The price is HK$2,115
HK$4,074 total
includes taxes & fees
9 May - 10 May
The Coastal Landing Stay

Beach house in Milford, CT

Beach house in Milford, CT
Milford
10.0 out of 10, Exceptional, (1 review)
"Beautiful Home right on the Long Island sound, we had such a great time. Beach was easily accessible, The Host’s were amazing and went above and beyond in accommodating us. Highly recommend!!!"
United States
Alex F.
The price is HK$5,287
HK$6,753 total
includes taxes & fees
30 Apr - 1 May
Beach house in Milford, CT

3-bedroom house just walking distance from Yale and Downtown

3-bedroom house just walking distance from Yale and Downtown
Dixwell
The price is HK$1,762
HK$3,256 total
includes taxes & fees
14 Apr - 15 Apr
3-bedroom house just walking distance from Yale and Downtown
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

Find out more about Thimble Islands

Thimble Islands Vacation Homes information

Number of reviews
279
Accommodation
313 Vacation Homes
Lowest Price
HK$1,210
Highest Price
HK$7,695

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