Thimble Islands Vacation Rentals

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Our top choices for Thimble Islands vacation rentals

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (38 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is CA $136
CA $279 total
includes taxes & fees
Apr 6 - Apr 7
1-bedroom cottage with Grove Beach 🏖️ access.

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (28 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is CA $173
CA $356 total
includes taxes & fees
Apr 4 - Apr 5
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Westbrook Center
The price is CA $157
CA $495 total
includes taxes & fees
Mar 31 - Apr 1
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

Shoreline Oasis

Shoreline Oasis
Clinton
9.2 out of 10, Wonderful, (7 reviews)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is CA $247
CA $363 total
includes taxes & fees
Apr 1 - Apr 2
Shoreline Oasis

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 CA $149
CA $370 total
includes taxes & fees
Mar 29 - Mar 30
Stylish Modern Stay Steps from the Ocean

Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (70 reviews)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
The price is CA $122
CA $247 total
includes taxes & fees
Mar 29 - Mar 30
Spacious 2 Bedroom apartment close to Yale Bowl

Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (6 reviews)
"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.
Cozy East Haven Home • Near Beach & Yale

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 CA $220
CA $733 total
includes taxes & fees
Mar 30 - Mar 31
Beachside Bliss w/ Game Room, Gym & Golf Green

Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.0 out of 10, Wonderful, (13 reviews)
"Conveniently located and nice, practically appointed stay for a business trip to work with a collaborator in town."
United States
Jeremy Y.
The price is CA $118
CA $299 total
includes taxes & fees
Mar 30 - Mar 31
Bright Downtown Studio near Yale & East Rock!

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.8 out of 10, Exceptional, (14 reviews)
"wonderful stay - great apartment and location and communication!"
United States
Anonymous traveller
The price is CA $145
CA $388 total
includes taxes & fees
Mar 30 - Mar 31
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
The price is CA $111
CA $258 total
includes taxes & fees
Mar 29 - Mar 30
One bedroom in United States of America, New Haven

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 CA $99
CA $213 total
includes taxes & fees
Mar 29 - Mar 30
Cozy Room in charming New Haven near Yale/Hospitals!

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is CA $180
CA $456 total
includes taxes & fees
Mar 27 - Mar 28
Angelica’s safe haven @ west haven

Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.6 out of 10, Exceptional, (10 reviews)
"Had a great stay!"
United States
Jeffrey C.
The price is CA $111
CA $258 total
includes taxes & fees
Mar 29 - Mar 30
Yale Casa Verde Studio

Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford
Milford
8.8 out of 10, Excellent, (3 reviews)
"Had a great stay!"
United States
Garry G.
The price is CA $155
CA $466 total
includes taxes & fees
Mar 30 - Mar 31
Beach Apartment in Woodmont Milford

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 CA $177
CA $339 total
includes taxes & fees
Mar 30 - Mar 31
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds

GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
East Rock
10.0 out of 10, Exceptional, (4 reviews)
"Great place - wish we had more than one night. "
United States
Steri-Clean N.
The price is CA $262
CA $614 total
includes taxes & fees
Mar 29 - Mar 30
GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds

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 CA $174
CA $313 total
includes taxes & fees
Mar 31 - Apr 1
Stocked home close to Yale, in Heart of New Haven

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 CA $175
CA $422 total
includes taxes & fees
Apr 19 - Apr 20
Once the old Schools house now a newly furnished Apartment

New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"This apartment was the perfect base for visiting family in Wallingford. It had everything we needed, was very clean, and super convenient to downtown cafes and restaurants. The train is a bit loud but to be expected! Will definitely stay again. "
United States
Kelsey S.
The price is CA $175
CA $421 total
includes taxes & fees
Apr 10 - Apr 11
New Railside Residents
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Thimble Islands. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.