Thimble Islands Holiday Rentals

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Holiday Rentals in Thimble Islands

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
10.0 out of 10, Exceptional, (49)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is AU$1,083
includes taxes & fees
3 Nov - 4 Nov
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"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!"
United States
Julie
The price is AU$404
includes taxes & fees
23 Oct - 24 Oct
Shoreline Oasis
Modern apartment in Westville/Yale Bowl area
10.0 out of 10, Exceptional, (32)
"We would stay here again in a heartbeat!"
United States
Denise B.
The price is AU$357
includes taxes & fees
1 Nov - 2 Nov
Modern apartment in Westville/Yale Bowl area
All New 1BR with tons of Charm
9.6 out of 10, Exceptional, (4)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AU$439
includes taxes & fees
31 Oct - 1 Nov
All New 1BR with tons of Charm
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
10.0 out of 10, Exceptional, (24)
"Overall wonderful experience, would highly recommend."
United States
Steven R.
The price is AU$400
includes taxes & fees
29 Oct - 30 Oct
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
10.0 out of 10, Exceptional, (33)
"Very much enjoyed our stay!"
United States
Barb D.
The price is AU$492
includes taxes & fees
22 Oct - 23 Oct
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
New 1BR Great Location Center of Town
10.0 out of 10, Exceptional, (2)
"Perfect spot for Oakdale Theater. Everything was as described and we were very comfortable. "
United States
Sarah W.
The price is AU$439
includes taxes & fees
29 Oct - 30 Oct
New 1BR Great Location Center of Town
Angelica’s safe haven @ west haven
10.0 out of 10, Exceptional, (5)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is AU$521
includes taxes & fees
23 Oct - 24 Oct
Angelica’s safe haven @ west haven
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
10.0 out of 10, Exceptional, (4)
"Great place - wish we had more than one night. "
United States
Steri-Clean N.
The price is AU$577
includes taxes & fees
22 Oct - 23 Oct
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
10.0 out of 10, Exceptional, (1)
"The studio apartment is in a very convenient location. It is a lovely walk to Yale. Many restaurants just outside the door. My friends, who joined me for a meal, found parking easily. It was a plus having use of a parking pass for Dwight Street. We never had a problem getting a parking spot. We also loved being able to bring our two small pups with us. The bottle of wine was a thoughtful touch. "
United States
ELIZABETH M S M.
The price is AU$337
includes taxes & fees
23 Oct - 24 Oct
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (33)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
The price is AU$273
includes taxes & fees
4 Nov - 5 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
The East Rock 4BR Parking Washer & Dryer Walk to Yale
10.0 out of 10, Exceptional, (5)
"We loved everything about our stay. The hosts were wonderful to work with and their home and the surrounding area are absolutely beautiful."
United States
Deanna K.
The price is AU$453
includes taxes & fees
22 Oct - 23 Oct
The East Rock 4BR Parking Washer & Dryer Walk to Yale
Newly Remodeled 1-BR Close to Everything yet Very Private
10.0 out of 10, Exceptional, (9)
"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. "
United States
Paula S.
The price is AU$451
includes taxes & fees
25 Oct - 26 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private
Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
The price is AU$747
includes taxes & fees
4 Nov - 5 Nov
Beachside Bliss w/ Game Room, Gym & Golf Green
All New Studio apartment in center of town
10.0 out of 10, Exceptional, (1)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is AU$439
includes taxes & fees
31 Oct - 1 Nov
All New Studio apartment in center of town
Cozy East Haven Home • Near Beach & Yale
10.0 out of 10, Exceptional, (4)
"Such a cute place, loved all the nautical touches. Great space for a weekend getaway, pretty well-stocked kitchen, clean & cozy. Really appreciated the outdoor space & amenities too! And Michael the host is very responsive & helpful! "
United States
Amal A.
The price is AU$254
includes taxes & fees
21 Nov - 22 Nov
Cozy East Haven Home • Near Beach & Yale
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
9.6 out of 10, Exceptional, (133)
"Great older house with everything you need to have a great time. Family event with 6 adults and 2 dogs enjoyed the house, the yard, and the area. Strongly recommend."
United States
Ray S.
The price is AU$902
includes taxes & fees
22 Oct - 23 Oct
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (9)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
United States
Jason K.
The price is AU$310
includes taxes & fees
22 Oct - 23 Oct
Charming Studio| Near Yale| Downtown New Haven
Once the old Schools house now a newly furnished Apartment
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$429
includes taxes & fees
31 Oct - 1 Nov
Once the old Schools house now a newly furnished Apartment
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"
United States
Derek L.
The price is AU$547
includes taxes & fees
3 Nov - 4 Nov
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Thimble Islands holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Thimble Islands holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Thimble Islands holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Thimble Islands holiday rentals we have selected for you start as low as AU$273 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Thimble Islands rentals

At Expedia, we put the best Thimble Islands holiday 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 holiday.

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.