Thimble Islands Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Thimble Islands vacation rentals

1 bedroom, desk, iron/ironing board, travel crib

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (34 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
$157 nightly
The price is $178
Jan 20 - Jan 21
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV, fireplace, books, music library

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.
$228 nightly
The price is $258
Jan 25 - Jan 26
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
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.
$433 nightly
The price is $490
Jan 20 - Jan 21
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Interior

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.
Adorable Cottage, 5 min walk to water & town
Apartment (2 Bedrooms) | Interior

Luxe Living! Apt 1 Mi to West Haven Medical Center

Luxe Living! Apt 1 Mi to West Haven Medical Center
3.0 star property
West Haven
$311 nightly
The price is $358
Jan 19 - Jan 20
Total with taxes and fees
Luxe Living! Apt 1 Mi to West Haven Medical Center
Private kitchen

Quintessential Essex. Steps from the Steam Train!

Quintessential Essex. Steps from the Steam Train!
2.0 star property
Essex
$273 nightly
The price is $309
Jan 21 - Jan 22
Total with taxes and fees
Quintessential Essex. Steps from the Steam Train!
Dining

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
2.0 star property
Clinton
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
$445 nightly
The price is $504
Jan 20 - Jan 21
Total with taxes and fees
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Interior

Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking
West New Haven
10.0 out of 10, Exceptional, (3 reviews)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
$214 nightly
The price is $214
Jan 19 - Jan 20
Total with taxes and fees
Westville Stay • 2BR • Near Yale • Free Parking
Property grounds

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.
$299 nightly
The price is $338
Jan 20 - Jan 21
Total with taxes and fees
Stylish Modern Stay Steps from the Ocean
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
$271 nightly
The price is $288
Jan 19 - Jan 20
Total with taxes and fees
All New 1BR with tons of Charm
Interior

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Saybrook Manor
9.6 out of 10, Exceptional, (134 reviews)
"We loved our stay!"
United States
Deana L.
$452 nightly
The price is $512
Jan 19 - Jan 20
Total with taxes and fees
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
1 bedroom, iron/ironing board, WiFi, bed sheets

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.
$271 nightly
The price is $288
Jan 19 - Jan 20
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Interior

All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
$271 nightly
The price is $288
Jan 19 - Jan 20
Total with taxes and fees
All New Studio apartment in center of town
Smart TV

Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (5 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.
$145 nightly
The price is $164
Feb 3 - Feb 4
Total with taxes and fees
Cozy East Haven Home • Near Beach & Yale
Cookware/dishes/utensils

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, (11 reviews)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
$263 nightly
The price is $274
Jan 21 - Jan 22
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Smart TV

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (15 reviews)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
$145 nightly
The price is $163
Jan 20 - Jan 21
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Interior

Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford
2.0 star property
Milford
9.0 out of 10, Wonderful, (2 reviews)
"Had a great stay!"
United States
Garry G.
$336 nightly
The price is $381
Jan 19 - Jan 20
Total with taxes and fees
Beach Apartment in Woodmont Milford
Exterior

Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
Downtown New Haven
9.0 out of 10, Wonderful, (12 reviews)
"Great location, exactly as advertised. The shades are somewhat translucent, so a bit bright at night, but wore a mask and it was fine. "
United States
Scott B.
$175 nightly
The price is $175
Jan 26 - Jan 27
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
Desk, iron/ironing board, WiFi, bed sheets

Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.6 out of 10, Exceptional, (8 reviews)
"Had a great stay!"
United States
Jeffrey C.
$180 nightly
The price is $204
Jan 19 - Jan 20
Total with taxes and fees
Yale Casa Verde Studio
Exterior

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
$307 nightly
The price is $348
Jan 20 - Jan 21
Total with taxes and fees
Angelica’s safe haven @ west haven
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"The room was larger than expected and breakfast was great! "
Dennis 1-night trip
Posted 1 day ago
Best Western Executive Hotel Of New Haven - West Haven

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 $175 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.

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