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, (40 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is CA $111
CA $249 total
includes taxes & fees
Apr 16 - Apr 17
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, (29 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 22 - Apr 23
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 $177
CA $522 total
includes taxes & fees
Apr 12 - Apr 13
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

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 $150
CA $371 total
includes taxes & fees
Apr 27 - Apr 28
Stylish Modern Stay Steps from the Ocean

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 $137
CA $377 total
includes taxes & fees
Apr 13 - Apr 14
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

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 $180
CA $322 total
includes taxes & fees
Apr 14 - Apr 15
Spacious 2 Bedroom apartment close to Yale Bowl

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 $192
CA $702 total
includes taxes & fees
Apr 14 - Apr 15
Beachside Bliss w/ Game Room, Gym & Golf Green

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
Apr 12 - Apr 13
One bedroom in United States of America, New Haven

All New Fully Furnished Cozy Studio

All New Fully Furnished Cozy Studio
Wallingford Center
9.8 out of 10, Exceptional, (8 reviews)
"Clean and well designed apartment in a great location. Book here if you are interested as you won't have any regrets. Enjoy! "
United States
Rick C.
The price is CA $191
CA $443 total
includes taxes & fees
Apr 11 - Apr 12
All New Fully Furnished Cozy Studio

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 $214 total
includes taxes & fees
Apr 12 - Apr 13
Cozy Room in charming New Haven near Yale/Hospitals!

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 $159
CA $400 total
includes taxes & fees
May 3 - May 4
Once the old Schools house now a newly furnished Apartment

Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.0 out of 10, Wonderful, (14 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 $141
CA $329 total
includes taxes & fees
Apr 13 - Apr 14
Bright Downtown Studio near Yale & East Rock!

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 $200
CA $483 total
includes taxes & fees
Apr 14 - Apr 15
Angelica’s safe haven @ west haven

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
Apr 14 - Apr 15
Stocked home close to Yale, in Heart of New Haven

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 $159
CA $401 total
includes taxes & fees
May 1 - May 2
New Railside Residents

All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
The price is CA $159
CA $401 total
includes taxes & fees
May 1 - May 2
All new 1BR apartment with all the features you are looking for

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 $260 total
includes taxes & fees
Apr 15 - Apr 16
Yale Casa Verde Studio

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
Apr 14 - Apr 15
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 CA $286
CA $717 total
includes taxes & fees
Apr 22 - Apr 23
The Jewel of The Cove - Historic Coastal Retreat

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 $239
CA $583 total
includes taxes & fees
Apr 12 - Apr 13
GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
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.