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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, (46 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $220
CA $389 total
includes taxes & fees
Jul 1 - Jul 2
1-bedroom cottage with Grove Beach 🏖️ access.

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is CA $323
CA $690 total
includes taxes & fees
Jun 28 - Jun 29
Adorable Cottage, 5 min walk to water & town

The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
10.0 out of 10, Exceptional, (24 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is CA $447
CA $709 total
includes taxes & fees
Jul 1 - Jul 2
The gardners Cottage 1 mile from long Island Sound - pet friendly

The Beach Nest-Lux Cottage Steps to the Beach

The Beach Nest-Lux Cottage Steps to the Beach
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"This is exactly what we needed. Nice area, great place to walk, easy to relax. "
United States
Karol W.
The price is CA $350
CA $837 total
includes taxes & fees
Jun 30 - Jul 1
The Beach Nest-Lux Cottage Steps to the Beach

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, (33 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is CA $224
CA $424 total
includes taxes & fees
Jul 7 - Jul 8
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
8.8 out of 10, Excellent, (6 reviews)
"Great host and property"
United States
Kevin K.
The price is CA $584
CA $1,024 total
includes taxes & fees
Jul 24 - Jul 25
Adorable Cottage with Cottage porch, walk to water & town

Near Yale & Lighthouse Point Beach: Home w/ Pool!

Near Yale & Lighthouse Point Beach: Home w/ Pool!
3.0 star property
East Shore
The price is CA $561
CA $1,059 total
includes taxes & fees
Jun 30 - Jul 1
Near Yale & Lighthouse Point Beach: Home w/ Pool!

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 $153
CA $346 total
includes taxes & fees
Jun 28 - Jun 29
Bright Downtown Studio near 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, (76 reviews)
"Spacious"
United States
Mehul
The price is CA $184
CA $328 total
includes taxes & fees
Jun 28 - Jun 29
Spacious 2 Bedroom apartment close to Yale Bowl

adorable ranch in beach community

adorable ranch in beach community
Old Saybrook
10.0 out of 10, Exceptional, (45 reviews)
"The experience was a pleasure - the house is comfy, and the location amazing! "
United States
Matthew V.
The price is CA $710
CA $1,193 total
includes taxes & fees
Jul 16 - Jul 17
adorable ranch in beach community

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, (139 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
The price is CA $532
CA $1,055 total
includes taxes & fees
Jul 1 - Jul 2
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is CA $167
CA $418 total
includes taxes & fees
Jun 28 - Jun 29
All New 1BR with tons of Charm

NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $348
CA $450 total
includes taxes & fees
Jul 1 - Jul 2
NEW Coastal Cottage 2 Miles to Beach + Lake Access

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
10.0 out of 10, Exceptional, (1 review)
"Clean & Comfortable, excellent accessibility to area restaurants & shopping.There was a hitch with my payment before check-in, the owner was helpful & communicative in resolving the issue.Overall, a great place to stay."
United States
Thomas S.
The price is CA $167
CA $418 total
includes taxes & fees
Jun 28 - Jun 29
All new 1BR apartment with all the features you are looking for

Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is CA $167
CA $418 total
includes taxes & fees
Jun 27 - Jun 28
Newly Remodeled with deck. Close to town center

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 CA $816
CA $1,411 total
includes taxes & fees
Jun 28 - Jun 29
Clear LI Sound waterview, Wedding pics, Yale&Beach

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 $167
CA $418 total
includes taxes & fees
Jul 7 - Jul 8
Once the old Schools house now a newly furnished Apartment

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 $206
CA $496 total
includes taxes & fees
Jul 1 - Jul 2
Angelica’s safe haven @ west haven

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
The price is CA $129
CA $284 total
includes taxes & fees
Jul 21 - Jul 22
One bedroom in United States of America, New Haven

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
East Rock
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
Australia
Nina
The price is CA $312
CA $696 total
includes taxes & fees
Jun 29 - Jun 30
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
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.

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