Thimble Islands Vacation Rentals

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Browse Select Thimble Islands Vacation Homes

Once the old Schools house now a newly furnished Apartment

9.0 out of 10, Wonderful, (12)
"The place was perfect for a quick weekend trip back to our hometown."
The price is CA $151
CA $388 total
includes taxes & fees
Aug 23 - Aug 24
Once the old Schools house now a newly furnished Apartment

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

9.8 out of 10, Exceptional, (6)
"We stayed for a week and the house was perfect. Comfortable, so clean, very well stocked, really nice decor and a fantastic location. Host was very helpful and responsive. Highly recommend and we will definitely be back. "
The price is CA $358
CA $727 total
includes taxes & fees
Sep 16 - Sep 17
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Newly Remodeled 1-BR Close to Everything yet Very Private

10.0 out of 10, Exceptional, (8)
"I was very pleased with the accomodations. I had everything I needed and it was comfortable and quiet. I was able to get my research done and enjoyed the peaceful setting, and it was convenient to the friends and family I visited during my stay. I will definitely stay here again. "
The price is CA $159
CA $401 total
includes taxes & fees
Aug 21 - Aug 22
Newly Remodeled 1-BR Close to Everything yet Very Private

Shoreline Oasis

9.0 out of 10, Wonderful, (6)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is CA $247
CA $356 total
includes taxes & fees
Aug 26 - Aug 27
Shoreline Oasis

Peace Barn in the heart of the CT River Valley

2.0 star property
8.6 out of 10, Excellent, (4)
"The grounds were beautiful Everything else for me and my family’ was awful and should not be rented as a vrbo. Lots of bugs. The upstairs bathroom had no water pressure or hot water. The upstairs bedroom window and screen were duct taped shut. The kitchen was a mishmash of things that didn’t work. The house did smell of mold. The only thing this property has to offer is the lake and the land the lodging was terrible and not at all comfortable. And the lights were terrible, if you could even...
The price is CA $553
CA $983 total
includes taxes & fees
Aug 21 - Aug 22
Peace Barn in the heart of the CT River Valley

The Jewel of The Cove - Historic Coastal Retreat

2.0 star property
10.0 out of 10, Exceptional, (4)
"loved it so much, beautiful property 100 % would stay again "
The price is CA $300
CA $730 total
includes taxes & fees
Sep 7 - Sep 8
The Jewel of The Cove - Historic Coastal Retreat

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is CA $304
CA $661 total
includes taxes & fees
Sep 15 - Sep 16
adorable ranch in beach community

McAngel Haven: 5 mins from Yale

10.0 out of 10, Exceptional, (12)
"Had a wonderful but short stay in New Haven. Home.of PEZ and PIZZA . "
The price is CA $317
CA $724 total
includes taxes & fees
Aug 19 - Aug 20
McAngel Haven: 5 mins from Yale

DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!

10.0 out of 10, Exceptional, (2)
"This property was great! Good location and loved the design of the place. I wish I could’ve stayed longer."
The price is CA $254
CA $590 total
includes taxes & fees
Aug 19 - Aug 20
DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!

Stocked home close to Yale, in Heart of New Haven

9.0 out of 10, Wonderful, (16)
"We loved our stay. It was just as expected and the host is responsive and friendly"
The price is CA $205
CA $347 total
includes taxes & fees
Aug 20 - Aug 21
Stocked home close to Yale, in Heart of New Haven

Cozy Home Near New Haven

10.0 out of 10, Exceptional, (1)
"So comfy for the dog and I for a night. Just what we needed!"
The price is CA $166
CA $218 total
includes taxes & fees
Sep 9 - Sep 10
Cozy Home Near New Haven

Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven

The price is CA $221
CA $420 total
includes taxes & fees
Aug 19 - Aug 20
Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven

Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking

9.6 out of 10, Exceptional, (8)
"Property owner takes great care of the place. Instructions were easy to follow and the location was right down the road from the places we were going to. We would rent again if we ever come back to New Haven"
The price is CA $246
CA $577 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking

Casa Soleada in East Rock |King Bed| Near DT and Yale SOM | Free parking

9.8 out of 10, Exceptional, (10)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
The price is CA $231
CA $566 total
includes taxes & fees
Sep 3 - Sep 4
Casa Soleada in East Rock |King Bed| Near DT and Yale SOM | Free parking

My little place Cozy Open concept for quiet time.

8.0 out of 10, Very good, (2)
"Great, clean property that was easy to access and very convenient to downtown Bridgeport. Perfect place to clean up and sleep. Very welcoming space."
The price is CA $205
CA $677 total
includes taxes & fees
Aug 21 - Aug 22
My little place Cozy Open concept for quiet time.

Charming 2-bedroom house with AC, WiFi in fantastic New Haven

8.0 out of 10, Very good, (1)
"The property inside was lovely. Every detail was thought of to make our stay delightful. Very comfortable beds. The neighborhood is in transition and it is rather noisy (cars driving by constantly) in the evenings. Not a deal breaker. We stayed on two separation occasions. Recommend for the convenience to downtown and Yale. "
Charming 2-bedroom house with AC, WiFi in fantastic New Haven

Welcome to your dream retreat!

8.0 out of 10, Very good, (1)
"Close to Westville shopping, Yale athletic fields/stadiums, events at SCSU, or a short drive or bus ride to downtown, Beaver Hill is a great neighborhood. I rented this property for overflow family in town for a wedding. The house is very clean and nicely appointed. While I would have like to see some cooking equipment (we're a family that likes to cook), I believe the owner has addressed this concern. This is a nice, comfortable, clean place perfect for a family. I would definitely rent...
The price is CA $480
CA $889 total
includes taxes & fees
Sep 15 - Sep 16
Welcome to your dream retreat!

Enchanting Retreat: Cozy 4bedroom Haven

The price is CA $242
CA $1,385 total
includes taxes & fees
Aug 30 - Aug 31
Enchanting Retreat: Cozy 4bedroom Haven

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

9.6 out of 10, Exceptional, (133)
"Very much enjoyed our trip! "
The price is CA $474
CA $878 total
includes taxes & fees
Aug 19 - Aug 20
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (18)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is CA $714
CA $1,191 total
includes taxes & fees
Aug 19 - Aug 20
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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