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
9.2 out of 10, Wonderful, (36)
"Very clean rustic cabin. The host was very accommodating. Fresh flowers and fruit were a nice touch from the host"
United States
Deb P.
$173 nightly
The price is $196
Jan 6 - Jan 7, 2026
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

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)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
$453 nightly
The price is $513
Jan 7 - Jan 8, 2026
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green

One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven
Dwight
10.0 out of 10, Exceptional, (2)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
$183 nightly
The price is $207
Dec 22 - Dec 23
Total with taxes and fees
One bedroom apartment in United States of America, New Haven

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, (27)
"Lovely location and the host does a wonderful job making it feel welcoming and calming inside with all the comfort of home. It is our 3rd or 4th time and we are already booked in December. The pictures and description on Vrbo match exactly. Highly recommend."
United States
Victoria S.
$226 nightly
The price is $256
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking
West New Haven
10.0 out of 10, Exceptional, (3)
"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.
$230 nightly
The price is $230
Jan 8 - Jan 9, 2026
Total with taxes and fees
Westville Stay • 2BR • Near Yale • Free Parking

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1)
"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.
$298 nightly
The price is $337
Dec 22 - Dec 23
Total with taxes and fees
Stylish Modern Stay Steps from the Ocean

Shoreline Oasis

Shoreline Oasis
Clinton
9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
$230 nightly
The price is $261
Dec 22 - Dec 23
Total with taxes and fees
Shoreline Oasis

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (7)
"I highly recommend this property!! We were in town for a wedding celebration, and it proved perfect. The property is completely updated, well-appointed and clean. The property is centrally located and close to restaurants, shops and grocery markets. Karl was a great host and communicated with us throughout our stay. I highly recommend!!"
United States
Francis S.
$271 nightly
The price is $288
Dec 27 - Dec 28
Total with taxes and fees
All New 1BR with tons of Charm

Quintessential Essex. Steps from the Steam Train!

Quintessential Essex. Steps from the Steam Train!
2.0 star property
Essex
$272 nightly
The price is $308
Dec 22 - Dec 23
Total with taxes and fees
Quintessential Essex. Steps from the Steam Train!

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.6 out of 10, Exceptional, (10)
"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.
$236 nightly
The price is $244
Dec 22 - Dec 23
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Killingworth
10.0 out of 10, Exceptional, (53)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
$610 nightly
The price is $691
Dec 29 - Dec 30
Total with taxes and fees
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6)
"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
$300 nightly
The price is $339
Dec 22 - Dec 23
Total with taxes and fees
Angelica’s safe haven @ west haven

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)
"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 4 - Jan 5, 2026
Total with taxes and fees
All New Studio apartment in center of town

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Saybrook Manor
9.6 out of 10, Exceptional, (133)
"We loved our stay!"
United States
Deana L.
$511 nightly
The price is $579
Dec 22 - Dec 23
Total with taxes and fees
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (1)
"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.
$271 nightly
The price is $288
Dec 29 - Dec 30
Total with taxes and fees
New Railside Residents

Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (4)
"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
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy East Haven Home • Near Beach & Yale

Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.

Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
Dwight
8.0 out of 10, Very Good, (2)
"The studio apartment is in a very convenient location. It is a lovely walk to Yale. Many restaurants just outside the door. My friends, who joined me for a meal, found parking easily. It was a plus having use of a parking pass for Dwight Street. We never had a problem getting a parking spot. We also loved being able to bring our two small pups with us. The bottle of wine was a thoughtful touch. "
United States
ELIZABETH M S M.
$224 nightly
The price is $232
Jan 8 - Jan 9, 2026
Total with taxes and fees
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.

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)
"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 2 - Jan 3, 2026
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment

Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale

Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale
East Shore
10.0 out of 10, Exceptional, (1)
"Had a Great stay at the nauti nook!"
United States
David D.
$391 nightly
The price is $443
Jan 12 - Jan 13, 2026
Total with taxes and fees
Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & 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

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 $141 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.