Search Thimble Islands Cottage Rentals from CA $134

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Browse Select Thimble Islands Cottages

Shalom Cottage with private beach rights.
Interior
Shalom Cottage with private beach rights.
9.2 out of 10, Wonderful, (13)
"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 CA $134
CA $253 total
includes taxes & fees
Sep 25 - Sep 26
Shalom Cottage with private beach rights.
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Exterior
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
10.0 out of 10, Exceptional, (67)
"Perfect and cozy home base for visiting with family!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Cozy cottage with Fireplace. Perfect place for local full festivals and wineries
Dining
Cozy cottage with Fireplace. Perfect place for local full festivals and wineries
2.0 star property
10.0 out of 10, Exceptional, (4)
"It was a perfect place to stay and be by the beach with the family. "
Cozy cottage with Fireplace. Perfect place for local full festivals and wineries
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach nearby, sun loungers, beach towels
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (98)
"Easy walk to the beach! Beach was great too. House was clean and spacious. "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Waterfront Cottage in Branford
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (83)
"We enjoyed our 2nd time at this house. Well-appointed and lots of space for our family to connect. Can’t beat the view!"
Waterfront Cottage in Branford
Guilford Carriage House at Granite Lodge!
TV
Guilford Carriage House at Granite Lodge!
10.0 out of 10, Exceptional, (7)
"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!
Historic Whitneyville Cottage
Fridge, microwave, oven, stovetop
Historic Whitneyville Cottage
9.6 out of 10, Exceptional, (12)
"Very convenient for what we needed. Nice little cottage."
Historic Whitneyville Cottage
Beach Bungalow, large porch, 1/2 mile to the water.
Fridge, microwave, oven, stovetop
Beach Bungalow, large porch, 1/2 mile to the water.
10.0 out of 10, Exceptional, (2)
"We stayed 10 days. Communication with the owners was excellent. The house was very clean and owners even stopped by after a few days and dropped off more towels. The porch was nice to sit and have a drink in the evening. The view from porch is a house across the street (no water view) the bedrooms have air conditioning. None on first floor but plenty of windows and screen door to allow airflow. They also have a grill which was a nice option that we used. Our favorite place to visit was a coffee...
The price is CA $270
CA $524 total
includes taxes & fees
Sep 24 - Sep 25
Beach Bungalow, large porch, 1/2 mile to the water.
Charming Deep River Vacation Rental on Star Lake!
Fridge, microwave, stovetop, dishwasher
Charming Deep River Vacation Rental on Star Lake!
8.8 out of 10, Excellent, (3)
"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!
Beach cottage on private beach!
Beach nearby, sun loungers, beach towels
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!
Cozy Country Cottage
TV, fireplace
Cozy Country Cottage
2.0 star property
8.8 out of 10, Excellent, (3)
"Get away from the hustle and bustle with this cute country cottage. Queen beds in the first floor and super cool loft, nice updates in the bathroom and kitchen. Window A/C units kept us cool on one of the hottest weeks of the year. Close to Derby and Route 15 made this a super-convenient stop-over for us as we came back from our honeymoon!"
Cozy Country Cottage
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
Aerial view
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
The Old Salt Cottage · Cozy Gateway Near Beach
Beach nearby
The Old Salt Cottage · Cozy Gateway Near Beach
10.0 out of 10, Exceptional, (4)
"The house looks so cute and cozy, but when you walked in and around, the house was up to date and spacious. All amenities and necessaries were provided for a wonderful stay, albeit way too short for such a lovely place."
The price is CA $520
CA $1,059 total
includes taxes & fees
Sep 24 - Sep 25
The Old Salt Cottage · Cozy Gateway Near Beach
Waterfront Cottage w/ Sunroom + Patio & Grill
Beach nearby
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
Smart TV
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
DIRECT WATERFRONT PRIVATE BEACH
Private beach
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
Property grounds
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
10.0 out of 10, Exceptional, (58)
"I and a group of friends stayed at Scott and Mary-Jo's VRBO for a fishing charter we had in Old Saybrook. We were very satisfied with our stay and the VRBO itself. They even made us homemade banana bread! Would highly recommend this VRBO."
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
The Perfect Family Beachfront Cottage The Viola Cottage
Property grounds
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
Property grounds
The gardners Cottage 1 mile from long Island Sound - pet friendly
10.0 out of 10, Exceptional, (11)
"We had a marvelous one week stay at Robin's cottage. Our host was very friendly and helpful. Location is very convenient and close to many points of interest, 5 Minutes to the beach, half an hour to New Haven or Gillette Castle. Thanks so very much"
The gardners Cottage 1 mile from long Island Sound - pet friendly
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See all available properties in Thimble Islands
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.
Terrace/patio
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
New Haven Village Suites
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1925)
"Excellent! Best kept secret in New Haven. My room was spacious. Lobby was beautiful and had coffee and breakfast. I would stay again, but you must have a car."
The price is CA $134
CA $154 total
includes taxes & fees
Oct 6 - Oct 7
New Haven Village Suites
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach nearby, sun loungers, beach towels
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (98)
"Easy walk to the beach! Beach was great too. House was clean and spacious. "
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 CA $134 and CA $520 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 86 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.