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.
$177 nightly
The price is $201
Mar 30 - Mar 31
Total with taxes and fees
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.
$225 nightly
The price is $255
Apr 4 - Apr 5
Total with taxes and fees
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
$315 nightly
The price is $357
Mar 31 - Apr 1
Total with taxes and fees
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.
$227 nightly
The price is $258
Apr 1 - Apr 2
Total with taxes and fees
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.
$233 nightly
The price is $264
Mar 29 - Mar 30
Total with taxes and fees
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.
$158 nightly
The price is $179
Mar 29 - Mar 30
Total with taxes and fees
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.
$469 nightly
The price is $531
Mar 30 - Mar 31
Total with taxes and fees
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.
$187 nightly
The price is $212
Mar 30 - Mar 31
Total with taxes and fees
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 traveler
$267 nightly
The price is $279
Mar 30 - Mar 31
Total with taxes and fees
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
$165 nightly
The price is $187
Mar 29 - Mar 30
Total with taxes and fees
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
$137 nightly
The price is $155
Mar 29 - Mar 30
Total with taxes and fees
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.
$306 nightly
The price is $347
Mar 28 - Mar 29
Total with taxes and fees
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.
$165 nightly
The price is $187
Mar 29 - Mar 30
Total with taxes and fees
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.
$282 nightly
The price is $319
Mar 30 - Mar 31
Total with taxes and fees
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.
$218 nightly
The price is $237
Mar 30 - Mar 31
Total with taxes and fees
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.
$389 nightly
The price is $441
Mar 29 - Mar 30
Total with taxes and fees
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
$195 nightly
The price is $221
Mar 31 - Apr 1
Total with taxes and fees
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.
$272 nightly
The price is $290
Apr 19 - Apr 20
Total with taxes and fees
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.
$278 nightly
The price is $296
Apr 10 - Apr 11
Total with taxes and fees
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

Everything you need to know about Thimble Islands vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Thimble Islands vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Thimble Islands vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Thimble Islands vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Thimble Islands. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Thimble Islands in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $155 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Thimble Islands rentals

At Expedia, we put the best Thimble Islands vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Thimble Islands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Thimble Islands vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Thimble Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.