Thimble Islands Vacation Rentals

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Vacation Rentals in Thimble Islands

Terrace/patio
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1830)
"Easy parking and safe open area"
The price is CA $138
CA $159 total
includes taxes & fees
Jun 9 - Jun 10
New Haven Village Suites
Beach nearby, sun loungers, beach towels
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (88)
"Positive experience, great location, and cozy accommodations for a centrally located family weekend."
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
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Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (110)
"I stayed at this amazing studio cottage with my girlfriend for 2 nights for her birthday. Our hosts, Liz and Adam were simply amazing. They allowed us an early check in and a late check out. Liz even brought out bicycles for us to use to tour around the neighborhood and ride along the shore line. Because it was my girlfriends birthday (or maybe they just do this), they had Prosecco and Orange Juice plus beer and cheese and other snacks for us when we arrived. The cottage is adorable, perfect...
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Beach nearby, beach towels
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
9.8 out of 10, Exceptional, (38)
"Great place. Cozy cottage!"
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
Business centre
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
9.8 out of 10, Exceptional, (20)
"Everything was okay, the apartment was great, enough space for 3 people. During the nighttime no noise, silence, good for well sleeping and so on… 5 points!"
Luxury Furnished Apartments by Hyatus Downtown at Yale
Smart TV, fireplace
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, (6)
"House was very nice. Location is great. Easy walk to beach and convenient to Westbrook center."
Patchogue River Retreat, 8 minute walk to West Beach
Beach nearby, sun loungers, beach towels
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (69)
"We very much enjoyed our stay and the host had everything prepared for us. The check in/out process was very easy as well!"
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach nearby, beach towels
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (15)
"Donna, the host, was absolutely wonderful. Very responsive. Cute beach bungalow. Very comfortable. Perfect for the three of us, 2 adults and 19 year old daughter. Would absolutely recommend."
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
View from property
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
9.8 out of 10, Exceptional, (22)
"Property exactly as described. What an amazing view and right on the beach. Great communication with host. Answered all our questions very promptly. Would definitely recommend."
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
On the beach, beach towels
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, (51)
"Wonderful host. Easy communication. Great house."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Interior
Shalom Cottage with private beach rights.
9.4 out of 10, Exceptional, (8)
"Has everything you need for 2, for a Summer stay. (The portable heater didn't keep up with the December evenings)."
The price is CA $163
CA $291 total
includes taxes & fees
May 31 - Jun 1
Shalom Cottage with private beach rights.
Property grounds
A TREETOPS Retreat! Upscale, Artsy 5 bedroom that sleeps 9-11, With POOL
10.0 out of 10, Exceptional, (15)
"By far the most unique architecture that we have ever stayed in. Every room is an adventure from its shape to the stunning artifacts from around the world. A gorgeous setting that was perfect for relaxing. Everything is first class-five star. So memorable that we are coming back next year."
A TREETOPS Retreat! Upscale, Artsy 5 bedroom that sleeps 9-11, With POOL
4 bedrooms, iron/ironing board, WiFi, bed sheets
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (80)
"The house is beautiful! Clean and organized. We had everything we needed and the view is incredible. We enjoyed the deck very much. So relaxing. My daughter (the bride) and her friends enjoyed getting ready there in the morning. I can’t say enough good things about this house."
Waterfront Cottage in Branford
Fridge, microwave, oven, stovetop
Spacious, beautiful home. 5-min walk to beach. 1 min to Water's Edge Resort!
10.0 out of 10, Exceptional, (41)
"Very nice place. Would definitely stay there again (actually this our second stay at the property). Clean, well equipped and the pictures are accurate."
Spacious, beautiful home. 5-min walk to beach. 1 min to Water's Edge Resort!
Property grounds
Beautiful 4BR Beach House with Private Beach Access.
10.0 out of 10, Exceptional, (65)
"Visited family back in CT and this was the perfect place to stay. Kind of like a Tardis, it was bigger on the inside! Thank you!"
Beautiful 4BR Beach House with Private Beach Access.
Property grounds
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
9.0 out of 10, Wonderful, (2)
"What a great place! Location, location. Located on edge of Little Italy with great restaurants and bars. Our favorite was Zenellis. Less than 15 minute walk to downtown New Haven with lots of dining options. Take in the Trinity Bar nearby- great fun! Furniture was modest but adequate. Great kitchen."
The price is CA $203
CA $426 total
includes taxes & fees
May 30 - May 31
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
Fridge, microwave, oven, stovetop
Spacious Victorian Loft
8.4 out of 10, Very good, (6)
"We liked the rental. It was spacious and we appreciated the complimentary coffee. The rental is also a more affordable option in New Haven and not too far away from downtown. It was easy to get in touch with the owner, but it would’ve been helpful if they provided us checkin information in a timely manner. If you’re a light sleeper this might not be the place for you. It’s located by a busy road. There were a lot of cars that were built to be as loud as possible revving their engines into...
The price is CA $131
CA $259 total
includes taxes & fees
May 27 - May 28
Spacious Victorian Loft
3 bedrooms, desk, WiFi, bed sheets
Direct Beachfront Property On Long Island Sound
10.0 out of 10, Exceptional, (26)
"We had a wonderful time on the beach, in the ocean and just relaxing in the house. There were nice restaurants in the area to try and some fun day trips to take with the kids. We'd go back!"
Direct Beachfront Property On Long Island Sound
Property grounds
The Dream Location for Your Perfect Vacation
9.8 out of 10, Exceptional, (15)
"The cottage has the most wonderful views! We loved our stay!"
The Dream Location for Your Perfect Vacation
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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.

Thimble Islands Vacation Rental Travel Info

Popular accommodation
Thimble Islands private vacation homes
International airport
New Haven, CT (HVN-Tweed - New Haven Regional)

Other types of properties in Thimble Islands you may be interested in

Exterior detail
New Haven Hotel
3.5 star property
8.8 out of 10, Excellent, (1236)
"Stayed only one night, location was quite close to Yale, within walking distance. Staff was friendly. Room was big but lots of unused space tbh. "
The price is CA $204
CA $235 total
includes taxes & fees
May 26 - May 27
New Haven Hotel
Terrace/patio
Hilton Garden Inn Shelton
3.0 star property
7.6 out of 10, Good, (1003)
"Great location to New Haven. Wonderful value for amenities. Very clean but definitely needs an update in rooms and lobby area."
The price is CA $156
CA $179 total
includes taxes & fees
Jun 10 - Jun 11
Hilton Garden Inn Shelton
Deluxe Room, 1 Queen Bed, Non Smoking
Best Western Executive Hotel Of New Haven - West Haven
2.5 star property
7.6 out of 10, Good, (1007)
"This was my third stay at this location. Quiet and safe place. Clean. However, more that half of the electric outlets in the room on the 5th floor were out of order."
The price is CA $155
CA $179 total
includes taxes & fees
Jun 16 - Jun 17
Best Western Executive Hotel Of New Haven - West Haven
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.

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Thimble Islands vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Thimble Islands vacation rentals we have selected for you start as low as CA $131 per night. Entering your travel dates in the search wizard 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. 

Recent reviews of Thimble Islands properties
Expedia verified reviews

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

5/5 Excellent
"Fun area clean room 19th floor bar so nice"
A verified traveller stayed at Omni New Haven Hotel at Yale
Posted 22 hours ago
Omni New Haven Hotel at Yale