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Compare 82 Cottages in Thimble Islands with updated reviews, rates, and availability.

Cozy Home near private beach , close to New Haven area colleges Hospitals
Property grounds
Cozy Home near private beach , close to New Haven area colleges Hospitals
9.6 out of 10, Exceptional, (54)
"What else can I say about this home it is absolutely beautiful They are sure to have it fully equipped they thought of everything toilet paper to coffee to wine they are the perfect hosts. I brought my dog and they have a nice little patio out in the yard he was able to run around there a little bit and do his thing. Across the street there is the beach and a trail and lighthouse Park is only a few minutes away and that was very nice as well. They are a lovely couple that on the home we are...
Cozy Home near private beach , close to New Haven area colleges Hospitals
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (102)
"We really enjoyed our stay. Beds, linens, towels all super comfortable. Kitchen bright and useful. Bathrooms spotless. 2 minute walk to cute beach. Tons of stuff to do in the area. Great, private backyard well appointed with portable fire pit, grill, furniture. Lots of kid games and books and puzzles in house. Need functional carbon monoxide detector. "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Welcome to our cute getaway
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
10.0 out of 10, Exceptional, (68)
"We really enjoyed our time away at this wonderful cottage!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Charming Deep River Vacation Rental on Star Lake!
Deep River Vacation Rental | 2BR | 1BA | Step Required | 618 Sq Ft
Charming Deep River Vacation Rental on Star Lake!
7.0 out of 10, Good, (4)
"Nice relaxing small house for a quick weekend getaway. Plenty of space in the kitchen and bedrooms. The shower is very very small, especially with a curtain that you kind of have to hold back away from you while you shower. If you like very firm beds youre in luck, the matresses are pretty firm. I would bring your own pillows as those provided were very thin. Other than that, its the perfect spot for a getaway. We had a wonderful relaxing weekend."
Charming Deep River Vacation Rental on Star Lake!
Shalom Cottage with private beach rights.
Exterior detail
Shalom Cottage with private beach rights.
9.0 out of 10, Wonderful, (17)
"This weekend was my daughters 16th birthday. She loves the beach, we were looking for a place we haven't been before. I came across this one and went for it. We were not disappointed at all. This was such a cute little spot. Very clean and quiet for being on a busier street. Its set back far enough you dont hear traffic. Raj sent a ton of restaurants in the area and other places to go as well. His mother greeted us upon arrival, she was very sweet. Overall a great stay and will be back! "
The price is AED 301
AED 610 total
includes taxes & fees
20 Nov - 21 Nov
Shalom Cottage with private beach rights.
Beach cottage on private beach!
Beach
Beach cottage on private beach!
10.0 out of 10, Exceptional, (4)
"It was a very nice cottage. Great price for staying right on the beach"
Beach cottage on private beach!
Waterfront Cottage in Branford
Exterior
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (87)
"The house was perfect for our annual getaway. We are a group of nine women who have been friends for over 45 years. The large well stocked kitchen with amazing view of the water and fireplace made our Friendsgiving meal memorable! The outdoor hot tub, fire pit, and deck with comfy seating topped off the weekend. Great location, plenty of parking, responsive host. 5/5 stars! "
Waterfront Cottage in Branford
The Dream Location for Your Perfect Vacation
Property grounds
The Dream Location for Your Perfect Vacation
9.8 out of 10, Exceptional, (16)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation
Private Island Compound with Large Cottage and Guest House
Cut in Two East Island
Private Island Compound with Large Cottage and Guest House
10.0 out of 10, Exceptional, (20)
"The island was the perfect vacation spot for a large family group! We enjoyed the paddle boards and kayaks daily , exploring the ocean and other Thimnle Islamds. We swam off the private beach when the rose was right and off the dock. The gazebo, porches and seating on the rocks were great for reading and boat and bird watching. The single storm was even a unique experience - weather and ocean on all sides! The ferry was convenient - making of island meals possible. E"
Private Island Compound with Large Cottage and Guest House
Guilford Carriage House at Granite Lodge!
Guilford Vacation Rental | 1BR | 1BA | Step-Free Access via Side Door
Guilford Carriage House at Granite Lodge!
10.0 out of 10, Exceptional, (8)
"We had a couple of out of town events in the are this past weekend, and it was also my birthday, so we decided to stay somplace special. The Granite Lodge Carriage hose was all of that! Beautifully decorated and furnished with lots of special touches from the host! We would definitely recommend, and will!"
Guilford Carriage House at Granite Lodge!
Waterfront Cottage w/ Sunroom + Patio & Grill
Clinton Vacation Rental | 2BR | 1BA | 720 Sq Ft | Step-Free Access
Waterfront Cottage w/ Sunroom + Patio & Grill
8.0 out of 10, Very Good, (5)
"Overall it was a nice relaxing stay. Nice and clean. Lots of sun through the back windows. Amenities were much appreciated, in kitchen, bathroom and bedrooms."
Waterfront Cottage w/ Sunroom + Patio & Grill
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Beach
Renovated Milford Beach home by Charles Island/Silver Sands Pk
10.0 out of 10, Exceptional, (2)
"Our family of 4 stayed comfortably. Towels and sheets were well stocked. We loved walking across to the beach. Our 10 year old could take our 5 year old. We biked on street and sidewalks to downtown Milford, public library, playground. We loved Pennys used books. It was such a relaxing trip and we will be back to stay at Susana's lovely place."
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Historic Whitneyville Cottage
Exterior detail
Historic Whitneyville Cottage
9.6 out of 10, Exceptional, (12)
"Very convenient for what we needed. Nice little cottage."
Historic Whitneyville Cottage
DIRECT WATERFRONT PRIVATE BEACH
Exterior
DIRECT WATERFRONT PRIVATE BEACH
9.4 out of 10, Exceptional, (23)
"I picked this rental because I recognized it as soon as I saw it! I grew up 5 houses from here. The rental was immaculate, the beach beautiful….home. Owners were very nice and helpful. They say you can’t go home again but I got pretty close! Fantastic spot. I’ll be back!"
DIRECT WATERFRONT PRIVATE BEACH
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
Front of Cottage
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
10.0 out of 10, Exceptional, (60)
"Our 2nd time to stay at this cozy little cottage. We always enjoy our time spent here. And we do enjoy the homemade banana bread."
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
The Perfect Family Beachfront Cottage The Viola Cottage
1.f10
The Perfect Family Beachfront Cottage The Viola Cottage
10.0 out of 10, Exceptional, (34)
"A fantastic visit! The cottage was so cute, quiet and right on the beach. Karl was an excellent host and so easy to work with. We will most definitely be back!!"
The Perfect Family Beachfront Cottage The Viola Cottage
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior
The gardners Cottage 1 mile from long Island Sound - pet friendly
10.0 out of 10, Exceptional, (12)
"Property is charming, beautifully decorated, clean. Host was very responsiveand even shared produce from her lovely garden! We hope to return."
The gardners Cottage 1 mile from long Island Sound - pet friendly
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Old Saybrook Vacation Rental | 3BR | 1BA | 2 Steps Required | 600 Sq Ft
'Grandma's Cottage' w/ Sunroom: Walk to Beach
8.0 out of 10, Very Good, (3)
"Terrific location. 1 block from the beach."
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
Room
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
10.0 out of 10, Exceptional, (14)
"This rental is so unique with the 2 sides, and was absolutely perfect for our wedding weekend. We had the groom’s friends staying on one side, and my friends staying on the other side. The two sides are connected through the sunroom and the backyard space is great which made bringing the whole group together so easy. The setup was also perfect for me to get ready on my own separate side the day of the wedding so that my now husband wouldn’t see me. The decor and cleanliness of the house were...
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
Beachfront Connecticut Retreat w/ Views!
Milford Vacation Rental | 3BR | 1.5BA | 832 Sq Ft | Steps to Access
Beachfront Connecticut Retreat w/ Views!
9.6 out of 10, Exceptional, (7)
"Just a wonderful beach cottage in a great spot that had all we needed"
Beachfront Connecticut Retreat w/ Views!
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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Other property types in Thimble Islands

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Beach/ocean view
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
New Haven Village Suites
Front of property
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1961)
"As always, clean and quiet."
The price is AED 364
AED 405 total
includes taxes & fees
25 Nov - 26 Nov
New Haven Village Suites
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (102)
"We really enjoyed our stay. Beds, linens, towels all super comfortable. Kitchen bright and useful. Bathrooms spotless. 2 minute walk to cute beach. Tons of stuff to do in the area. Great, private backyard well appointed with portable fire pit, grill, furniture. Lots of kid games and books and puzzles in house. Need functional carbon monoxide detector. "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
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.

Frequently asked questions

How much do cottages in Thimble Islands cost?
Cottages in Thimble Islands range between AED 301 and AED 301 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Thimble Islands?
You can choose from 82 cottages in Thimble Islands. No matter if you’re vacationing with the family or planning a getaway with close friends, Expedia can help you find the right place to enjoy nature’s beauty.
Why book your cottage in Thimble Islands with Expedia?
Reserving a cottage in Thimble Islands is as easy as entering your travel dates and selecting an ideal place for a vacation in the outdoors. From luxurious retreats to budget-friendly properties and cottages that offer perks like a hot tub, Expedia has something for all styles and tastes. As for unbeatable deals? We’ve got them as well!
How can I find cheap cottages in Thimble Islands?
With Expedia’s handy filter tool, scoring cheap cottages in Thimble Islands has never been simpler. To find accommodations that’ll make your bank balance smile, refine your search by amenities, star rating and budget.