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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, (49 reviews)
"We enjoyed our stay"
United States
JM B.
$234 nightly
The price is $265
Jul 21 - Jul 22
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

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.
$173 nightly
The price is $196
Jul 21 - Jul 22
Total with taxes and fees
One bedroom in United States of America, New Haven

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
$319 nightly
The price is $361
Jul 20 - Jul 21
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

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.
$215 nightly
The price is $244
Jul 19 - Jul 20
Total with taxes and fees
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.
$307 nightly
The price is $348
Jul 22 - Jul 23
Total with taxes and fees
Angelica’s safe haven @ west haven

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
Fair Haven
$98 nightly
The price is $110
Jul 16 - Jul 17
Total with taxes and fees
Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.4 out of 10, Exceptional, (16 reviews)
"wonderful stay - great apartment and location and communication!"
United States
Anonymous traveler
$288 nightly
The price is $302
Jul 21 - Jul 22
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

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, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$274 nightly
The price is $292
Jul 21 - Jul 22
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment

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)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
$247 nightly
The price is $280
Aug 4 - Aug 5
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Beautiful Downtown New Haven Retreat

Beautiful Downtown New Haven Retreat
Downtown New Haven
$284 nightly
The price is $322
Jul 16 - Jul 17
Total with taxes and fees
Beautiful Downtown New Haven Retreat

Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very Good, (8 reviews)
"The place was incredibly clean. The instructions were clear for entering and locking up. Great experience! Thanks Dylan. "
United States
Andrew P.
$225 nightly
The price is $254
Jul 22 - Jul 23
Total with taxes and fees
Spacious Bohemian Nook

Peaceful Private Stay in Shared Home Near Yale

Peaceful Private Stay in Shared Home Near Yale
West New Haven
10.0 out of 10, Exceptional, (1 review)
"This place was just perfect for us and our stay. The neighborhood was safe, and the property was easy to find. Bedroom was cozy, and the communication with the host was phenomenal. Thank you!"
United States
McKenna S.
$183 nightly
The price is $207
Jul 19 - Jul 20
Total with taxes and fees
Peaceful Private Stay in Shared Home Near Yale

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.
$221 nightly
The price is $240
Jul 16 - Jul 17
Total with taxes and fees
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Cozy Stay by Little Italy & Wooster Street

Cozy Stay by Little Italy & Wooster Street
Mill River
10.0 out of 10, Exceptional, (2 reviews)
"This apartment in a 4 unit building with its own parking lot was on a quiet street. Easy to get to no matter what side of the city I came from and close enough to walk to downtown (6 blocks) and half a block off the famous Little Italy street for food and cocktails and then brunch and coffee in walking distance in the mornings too. The unit had everything you need, fully stocked kitchen and bath, shared laundry. Great mattress and pillows! Easy keypad entry. I’d stay there over and over again!"
United States
Erica S.
$273 nightly
The price is $309
Jul 19 - Jul 20
Total with taxes and fees
Cozy Stay by Little Italy & Wooster Street

Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven

Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven
Foxon
10.0 out of 10, Exceptional, (1 review)
"Place looks way better in person, cozy and quiet. Loved the backyard and deck also plenty of fast food restaurants and Walmart near by."
United States
Fateema M.
$268 nightly
The price is $303
Jul 20 - Jul 21
Total with taxes and fees
Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven

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.
$271 nightly
The price is $289
Aug 11 - Aug 12
Total with taxes and fees
All New 1BR with tons of Charm

Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay in town when visiting family! Kitchen was well stocked, location was convenient, & it had everything we needed!"
United States
Jennifer L.
$274 nightly
The price is $292
Jul 18 - Jul 19
Total with taxes and fees
Fully Furnished 1BR Apartment

Relaxing 3-bedroom apartment in New Haven

Relaxing 3-bedroom apartment in New Haven
New Haven
8.0 out of 10, Very Good, (1 review)
"To be honest with you overall the stay was decent. The host was very accommodating for us as we wanted to check in early due to our flight, arriving in the morning. When we had issues with the linens needing to be changed I called our host she was super responsive and immediately had housekeeping there to rectify our issues. The only thing I could say about the property is the furniture, especially in the living area needs to be updated. Also, the property could use some TLC when it comes to the...
United States
S F.
$339 nightly
The price is $384
Jul 16 - Jul 17
Total with taxes and fees
Relaxing 3-bedroom apartment in New 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, (25 reviews)
"Easy check in. The property was big, comfortable and clean. "
United States
Jesse L.
$204 nightly
The price is $231
Jul 19 - Jul 20
Total with taxes and fees
Stocked home close to Yale, in Heart of New Haven

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.
$517 nightly
The price is $585
Jul 19 - Jul 20
Total with taxes and fees
The Beach Nest-Lux Cottage Steps to the Beach
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 $265 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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