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Thimble Islands Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Thimble Islands vacation rentals

A two-story house with a covered porch, a front door, and a small outdoor seating area with a table and chairs.

1. Cozy Home near private beach , close to New Haven area colleges Hospitals

Cozy Home near private beach , close to New Haven area colleges Hospitals
Branford
9.4 out of 10, Exceptional, (84 reviews)
"Property was clean with some nice cozy touches. Wine on the table, fruit in the frig, chocolate for comfort, coffee for wakeup. Host was very pleasant and accommodating. Will definitely stay there again."
United States
Vincent
$265 nightly
The price is $300
Nov 2 - Nov 3
Total with taxes and fees
Cozy Home near private beach , close to New Haven area colleges Hospitals
A spacious lobby with a large chandelier, a central round table with a vase, and a checkered floor.

2. Yale Deluxe Modern Apartment

Yale Deluxe Modern Apartment
Downtown New Haven
10.0 out of 10, Exceptional, (1 review)
"Great spot close to everything with a secure entrance to the building. Easy access to the unit Quick responses and good communication from the host. Great unit with lots of amenities! Definitely would stay here again and again!!"
United States
Anonymous traveler
$199 nightly
The price is $199
Nov 9 - Nov 10
Total with taxes and fees
Yale Deluxe Modern Apartment
A living room with a dark grey sofa, a wooden coffee table with a vase of white flowers, a patterned rug, and a ceiling fan.

3. Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (12 reviews)
"Property was clean and had all amenities we needed. Easy check in and check out"
United States
Sarah S.
$188 nightly
The price is $213
Nov 9 - Nov 10
Total with taxes and fees
Cozy East Haven Home • Near Beach & Yale
A row of brownstone buildings with a central staircase leading to the second floor.

4. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.2 out of 10, Wonderful, (17 reviews)
"Pretty close to Yale campus"
United States
Dongjian
$215 nightly
The price is $244
Oct 25 - Oct 26
Total with taxes and fees
Bright Downtown Studio near Yale & East Rock!
A building with a blue entrance marked 'welcome,' a brick facade, and a covered parking area.

5. MS6 Branford | 1 King Bed Smk, Micfridge

MS6 Branford | 1 King Bed Smk, Micfridge
Branford
10.0 out of 10, Exceptional, (50 reviews)
"Those beds were very large and super cozy!"
United States
Anonymous traveler
$85 nightly
The price is $98
Nov 1 - Nov 2
Total with taxes and fees
MS6 Branford | 1 King Bed Smk, Micfridge
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

6. One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.4 out of 10, Exceptional, (3 reviews)
"The property is immaculate and the service very responsive."
United States
Stephanie G.
$161 nightly
The price is $182
Oct 26 - Oct 27
Total with taxes and fees
One bedroom in United States of America, New Haven
A row of brick townhouses with wooden front doors, black railings, and a sidewalk.

7. Prime Yale Studio Steps to Sallys Apizza

Prime Yale Studio Steps to Sallys Apizza
Downtown New Haven
10.0 out of 10, Exceptional, (2 reviews)
"Great stay - and it is close to Sally's! We had a nice visit and all was as represented for the property."
United States
Milton W.
$188 nightly
The price is $212
Oct 25 - Oct 26
Total with taxes and fees
Prime Yale Studio Steps to Sallys Apizza
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

8. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (63 reviews)
"We enjoyed our stay"
United States
JM B.
$205 nightly
The price is $233
Oct 26 - Oct 27
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
A spacious living area with a wooden floor, a sofa, a coffee table, and a TV mounted on the wall.

9. Modern Loft near Yale and Wooster Square + Parking

Modern Loft near Yale and Wooster Square + Parking
Downtown New Haven
10.0 out of 10, Exceptional, (1 review)
"Great location. Safe and walking distance to many great restaurants. Very clean"
United States
mary dawn h.
$235 nightly
The price is $266
Oct 26 - Oct 27
Total with taxes and fees
Modern Loft near Yale and Wooster Square + Parking
A dining area with a long table, four chairs, a chandelier, and a painting on the wall.

10. Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (80 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
$185 nightly
The price is $209
Oct 26 - Oct 27
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl
A neatly made bed with a checkered blanket, white pillows, and a framed picture on the wall.

11. Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.2 out of 10, Wonderful, (15 reviews)
"We had a very nice stay here! The hosts were lovely and very communicative, and they were able to help us with any problems we had very quickly."
United States
Luke
$163 nightly
The price is $185
Nov 2 - Nov 3
Total with taxes and fees
Yale Casa Verde Studio
A kitchen with white cabinets, a stove, and a dining table with chairs.

12. Yale Science Park 1BR | Free Parking

Yale Science Park 1BR | Free Parking
Dixwell
8.0 out of 10, Very good, (8 reviews)
"The property had everything needed and was a short distance to so many campus sites. Would definitely stay again."
United States
Natalie B.
$215 nightly
The price is $244
Oct 26 - Oct 27
Total with taxes and fees
Yale Science Park 1BR | Free Parking
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

13. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
7.6 out of 10, Good, (5 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
$212 nightly
The price is $229
Oct 28 - Oct 29
Total with taxes and fees
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
A modern living room with a large mirror, a wooden accent wall, a grey sofa, and a large window with white curtains.

14. The Elm - Retreat Near Yale, Parking, Gym, DTWN, Wooster Sq & Union Stn.

The Elm - Retreat Near Yale, Parking, Gym, DTWN, Wooster Sq & Union Stn.
Downtown New Haven
10.0 out of 10, Exceptional, (6 reviews)
"Great little downtown apartment! Small - good for up to two people. Nicely appointed and decorated, great sectional sofa, big TVs where we wanted them. Host was kind and helpful and accommodating. Location is pretty much across State St from the State Street RR Station, a block and a half from the Green, and near everything. Orange Street (half a block away) has a ton of bars and restaurants. We enjoyed our stay!"
United States
George Z.
$294 nightly
The price is $333
Oct 26 - Oct 27
Total with taxes and fees
The Elm - Retreat Near Yale, Parking, Gym, DTWN, Wooster Sq & Union Stn.
Downtown New Haven Vacation Rental Near Yale – Admire the historic Yale architecture just steps from your apartment, immersing yourself in the university’s rich heritage.

15. Bright Downtown New Haven Escape

Bright Downtown New Haven Escape
Downtown New Haven
9.8 out of 10, Exceptional, (6 reviews)
"In the heart of downtown New Haven and convenient to everything."
United States
Stewart C.
$291 nightly
The price is $329
Oct 31 - Nov 1
Total with taxes and fees
Bright Downtown New Haven Escape
A modern kitchen with a sink, countertop, and a dishwasher. There is a blue sofa with a window view and a bed in the adjacent room.

16. Luxury Studio Near Yale | Gym, W/D & Fast WiFi

Luxury Studio Near Yale | Gym, W/D & Fast WiFi
Downtown New Haven
8.0 out of 10, Very good, (2 reviews)
"The location is excellent - right on the Green and near bus stops including the free bus from the train station. There is a great little market on the first floor of the building. The owner was very responsive to questions, but our visit was marred by the fact that the smoke detector chirped every 23 seconds day and night. The owner knew about this from the moment we checked in but did not fix it during the 2 days we were there. Until this is fixed he should warn renters ahead of time so...
United States
Julianne P.
$207 nightly
The price is $207
Oct 28 - Oct 29
Total with taxes and fees
Luxury Studio Near Yale | Gym, W/D & Fast WiFi
Live in style in Historic Little Italy! Our stunning living room awaits in a vibrant downtown location near Yale.

17. Cozy Stay by Little Italy & Wooster Street

Cozy Stay by Little Italy & Wooster Street
Wooster Square
7.6 out of 10, Good, (5 reviews)
"This apartment in a 4 unit building with its own parking lot was on a quiet street. Easy to get to no matter what side of the city I came from and close enough to walk to downtown (6 blocks) and half a block off the famous Little Italy street for food and cocktails and then brunch and coffee in walking distance in the mornings too. The unit had everything you need, fully stocked kitchen and bath, shared laundry. Great mattress and pillows! Easy keypad entry. I’d stay there over and over again!"
United States
Erica S.
$273 nightly
The price is $309
Oct 25 - Oct 26
Total with taxes and fees
Cozy Stay by Little Italy & Wooster Street
A living room with a flat-screen TV mounted on the wall, a yellow armchair, a patterned rug, and various decorative items on shelves and side tables.

18. The Sicilian

The Sicilian
West New Haven
9.2 out of 10, Wonderful, (17 reviews)
"It was the perfect day and very convenient for our trip for our son’s graduation. Thank you for being so receptive and helpful."
United States
Michele B.
$212 nightly
The price is $240
Oct 25 - Oct 26
Total with taxes and fees
The Sicilian
A living room with a sofa, coffee table, and a large mirror. There are windows, a plant, and a bookshelf.

19. A brick's throw away to Sally's Apizza!

A brick's throw away to Sally's Apizza!
Wooster Square
8.8 out of 10, Excellent, (5 reviews)
"The perfect place for visiting my Yale student! The space was comfortable for her to come visit, far enough from campus for a beak but close enough to get to class. Loved the full kitchen to provide her a home cooked meal and access to the washer and dryer so we could do her laundry. We can’t wait to stay again! I highly recommend both coffee locations and the liquor store in the neighborhood. And of course Sally’s! The host was amazing and communicated nearly immediately when I had questions! "
United States
Brandi J.
$282 nightly
The price is $319
Oct 25 - Oct 26
Total with taxes and fees
A brick's throw away to Sally's Apizza!
A beach with a house in the background, a clear sky, and a calm sea.

20. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
$314 nightly
The price is $356
Oct 27 - Oct 28
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
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

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

10/10 Excellent
"Happy Hour. Top Tier. Left Before Breakfast"
Ray 1-night trip
Posted 1 hour ago
Cambria Hotel New Haven University Area

Find out more about Thimble Islands

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, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

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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 low season months. For more hustle and bustle, you may prefer to visit Thimble Islands in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $79 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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