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Thimble Islands Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Thimble Islands vacation rentals

A hotel room with a bed, bedside table with a phone, a desk with a chair, a TV, and a door leading to another room.

1. Cozy 1 King Bed | Smoking

Cozy 1 King Bed | Smoking
Branford
10.0 out of 10, Exceptional, (55 reviews)
"Before morning travel, we got much-needed rest here. Rooms had ample space so it didn't feel cramped at all, plus friendly staff shared helpful breakfast recommendations as part of our group treat experience."
United States
Anonymous traveler
$79 nightly
The price is $91
Dec 3 - Dec 4
Total with taxes and fees
Cozy 1 King Bed | Smoking
A row of brick townhouses with wooden front doors, black railings, and a sidewalk.

2. 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.
$200 nightly
The price is $227
Nov 5 - Nov 6
Total with taxes and fees
Prime Yale Studio Steps to Sallys Apizza
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

3. 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.
$158 nightly
The price is $179
Nov 30 - Dec 1
Total with taxes and fees
One bedroom in United States of America, New Haven
A spacious lobby with a large chandelier, a central round table with a vase, and a checkered floor.

4. 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
$170 nightly
The price is $170
Nov 30 - Dec 1
Total with taxes and fees
Yale Deluxe Modern Apartment
Interior

5. Château Blanc | Near Yale University

Château Blanc | Near Yale University
Dwight
8.6 out of 10, Excellent, (9 reviews)
"Perfect for a quick trip and one night stay!"
United States
Chris D.
$160 nightly
The price is $183
Nov 9 - Nov 10
Total with taxes and fees
Château Blanc | Near Yale University
A row of brownstone buildings with a central staircase leading to the second floor.

6. 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
$237 nightly
The price is $270
Nov 8 - Nov 9
Total with taxes and fees
Bright Downtown Studio near Yale & East Rock!
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.

7. 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.
$137 nightly
The price is $157
Nov 9 - Nov 10
Total with taxes and fees
Cozy East Haven Home • Near Beach & Yale
A two-story house with a covered porch, a front door, and a small outdoor seating area with a table and chairs.

8. 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, (86 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
$254 nightly
The price is $289
Nov 17 - Nov 18
Total with taxes and fees
Cozy Home near private beach , close to New Haven area colleges Hospitals
A hotel room with two beds, a desk, and a chair.

9. Spacious 2 Full Beds Nsmk

Spacious 2 Full Beds Nsmk
Branford
10.0 out of 10, Exceptional, (52 reviews)
"Really appreciated the clean, spacious feel throughout my stay."
United States
Anonymous traveler
$79 nightly
The price is $91
Dec 3 - Dec 4
Total with taxes and fees
Spacious 2 Full Beds Nsmk
A neatly made bed with a checkered blanket, white pillows, and a framed picture on the wall.

10. 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
$153 nightly
The price is $174
Nov 23 - Nov 24
Total with taxes and fees
Yale Casa Verde Studio
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.

11. 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.
$171 nightly
The price is $171
Nov 30 - Dec 1
Total with taxes and fees
Luxury Studio Near Yale | Gym, W/D & Fast WiFi
A living room with a TV, sofa, coffee table, and a staircase leading to an upper level.

12. Modern Loft Near Yale |Wooster Sq| 5 Star Location

Modern Loft Near Yale |Wooster Sq| 5 Star Location
Downtown New Haven
10.0 out of 10, Exceptional, (1 review)
"My wife and I loved this unit. The host was the quickest to respond to questions that we have encountered. My only issue was the parking. There is a 19 charge per day to park in the parking lot. There is limited and restricted street parking. We got lucky because we were there on a weekend night."
United States
Eric P.
$252 nightly
The price is $287
Nov 23 - Nov 24
Total with taxes and fees
Modern Loft Near Yale |Wooster Sq| 5 Star Location
A beach with a house in the background, a clear sky, and a calm sea.

13. 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.
$305 nightly
The price is $347
Nov 6 - Nov 7
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A dining area with a long table, four chairs, a chandelier, and a painting on the wall.

14. 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.
$180 nightly
The price is $205
Nov 16 - Nov 17
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl
A modern hotel room with a bed, bedside table, desk, chair, and a flat-screen TV.

15. 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
$83 nightly
The price is $95
Dec 3 - Dec 4
Total with taxes and fees
MS6 Branford | 1 King Bed Smk, Micfridge
A modern living room with a gray sofa, a dining table with white chairs, a small coffee table, and a potted plant.

16. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
8.0 out of 10, Very good, (6 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.
$202 nightly
The price is $219
Nov 9 - Nov 10
Total with taxes and fees
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
A modern hotel room with a bed, bedside table, chair, desk, and a television.

17. Cozy 1 King Bed | Non-Smoking

Cozy 1 King Bed | Non-Smoking
Branford
10.0 out of 10, Exceptional, (55 reviews)
"Stayed one night, quick checkout process got me back on road promptly!"
United States
Anonymous traveler
$79 nightly
The price is $91
Dec 3 - Dec 4
Total with taxes and fees
Cozy 1 King Bed | Non-Smoking
A hotel room with a bed, bedside table with a phone, a desk with a chair, a TV, and a window with curtains.

18. 1 King Bed | Mob Acc Tub, Nsmk

1 King Bed | Mob Acc Tub, Nsmk
Branford
10.0 out of 10, Exceptional, (51 reviews)
"Quiet evenings with an easy check-in process made this place worth returning to if passing by again soon."
United States
Anonymous traveler
$80 nightly
The price is $92
Dec 3 - Dec 4
Total with taxes and fees
1 King Bed | Mob Acc Tub, Nsmk
A living room with a wooden floor, a television on a white stand, a dining table with books, and a chair with a blanket.

19. 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.
$222 nightly
The price is $253
Nov 8 - Nov 9
Total with taxes and fees
Yale Science Park 1BR | Free Parking
A hotel room with two beds, a desk, and a chair.

20. Cozy 2 Full Beds Micfridge Parking

Cozy 2 Full Beds Micfridge Parking
Branford
10.0 out of 10, Exceptional, (50 reviews)
"The rooms offered a quiet space that was perfect for resting."
United States
Anonymous traveler
$82 nightly
The price is $94
Dec 3 - Dec 4
Total with taxes and fees
Cozy 2 Full Beds Micfridge 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

Quality Inn

Quality Inn

10/10 Excellent
"Clean room staff friendly"
Najera 1-night trip
Posted 2 hours ago
Quality Inn

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 $78 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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