Thimble Islands Holiday Rentals

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Check prices for these dates

Tonight
11 Nov - 12 Nov
Tomorrow
12 Nov - 13 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

Holiday Rentals in Thimble Islands

Terrace/patio
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Branford
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
In-room dining
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
The Hill
9.6 out of 10, Exceptional, (60)
"Wonderful property- brand new building, nice spacious rooms perfect for family. Instructors for check in and out and everything in between very clear and helpful. "
United States
Zhuo
Luxury Furnished Apartments by Hyatus Downtown at Yale
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton
9.2 out of 10, Wonderful, (36)
"Host was very friendly and accommodating"
United States
Monika M.
The price is HK$804
HK$1,710 total
includes taxes & fees
12 Nov - 13 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior
Shoreline Oasis

Shoreline Oasis

Clinton
9.2 out of 10, Wonderful, (7)
"Cute apartment in a house, separate from the hosts space downstairs. Clean and walking distance to some great harbor-front restaurants. 1 bed and 2 couches (no pull-out couch)"
United States
Molly H.
The price is HK$1,392
HK$2,026 total
includes taxes & fees
17 Nov - 18 Nov
Shoreline Oasis
Seasonal outdoor pool
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4.0 star property
The Hill
9.4 out of 10, Exceptional, (21)
"Great. Would prefer to anyone"
United States
Bryan
Luxury Apartments by Hyatus at Pierpont
Exterior
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

Downtown New Haven
9.0 out of 10, Wonderful, (10)
"Nice location in downtown New Haven. The room itself is nice and convenient. The window near the bed does not close because there is a large tube going through the window with tape around it. On a chilly day/night this is not comfortable and there is nothing one can do since the window does not close. You can also hear everything going on outside because the window does not close. Bedsheets were not clean either. Contacted the host about the window and bedsheets and the host gave me the...
United States
Noel
The price is HK$855
HK$1,796 total
includes taxes & fees
20 Nov - 21 Nov
Charming Studio| Near Yale| Downtown New Haven
Outdoor dining
DIRECT WATERFRONT with awesome views and near Yale

DIRECT WATERFRONT with awesome views and near Yale

West Haven
10.0 out of 10, Exceptional, (2)
"Great place to stay! Easy for an overnight for a family wedding!"
United States
Phoebe T.
The price is HK$2,177
HK$3,570 total
includes taxes & fees
26 Nov - 27 Nov
DIRECT WATERFRONT with awesome views and near Yale
Dining
Scenic Waterfront Beach Home-Private Beach, Hot Tub & Panoramic Views

Scenic Waterfront Beach Home-Private Beach, Hot Tub & Panoramic Views

Branford
10.0 out of 10, Exceptional, (71)
"Beautiful property and neighborhood! The beds were super comfy and the kitchen well- stocked with essentials."
United States
Beth U.
Scenic Waterfront Beach Home-Private Beach, Hot Tub & Panoramic Views
Fridge, microwave, oven, stovetop
New Cozy 2BR Stay New Haven Close to Yale

New Cozy 2BR Stay New Haven Close to Yale

2.0 star property
East Rock
7.4 out of 10, Good, (3)
"Check-in was fine. Once we got in the space was small. The dishes in the kitchen and the bed in the master bedroom were dirty. "
United States
Kristin R.
The price is HK$1,454
HK$2,199 total
includes taxes & fees
18 Nov - 19 Nov
New Cozy 2BR Stay New Haven Close to Yale
1 bedroom, WiFi, bed sheets
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

2.0 star property
West New Haven
9.0 out of 10, Wonderful, (2)
"Great communication and easy check in, would recommend "
United States
Ethan R.
The price is HK$622
HK$1,005 total
includes taxes & fees
4 Dec - 5 Dec
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
Interior
Beach house in Milford, CT

Beach house in Milford, CT

Milford
10.0 out of 10, Exceptional, (1)
"Beautiful Home right on the Long Island sound, we had such a great time. Beach was easily accessible, The Host’s were amazing and went above and beyond in accommodating us. Highly recommend!!!"
United States
Alex F.
The price is HK$5,597
HK$7,183 total
includes taxes & fees
12 Nov - 13 Nov
Beach house in Milford, CT
Exterior
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison
10.0 out of 10, Exceptional, (36)
"The place was adorable and spotless, the beds were super comfortable it was perfect and a minute from the beach! We will be back. Thanks for a great time!"
United States
Edward
The price is HK$1,680
HK$2,150 total
includes taxes & fees
12 Nov - 13 Nov
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Interior
Stunning Apt W/ Parking and Gym | Downtown at Yale

Stunning Apt W/ Parking and Gym | Downtown at Yale

The Hill
10.0 out of 10, Exceptional, (46)
"High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again."
United Kingdom
Coco N.
Stunning Apt W/ Parking and Gym | Downtown at Yale
Dining
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Old Saybrook
10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
United States
Nicole L.
The price is HK$5,558
HK$9,191 total
includes taxes & fees
27 Nov - 28 Nov
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Exterior
Angelica’s safe haven @ west haven

Angelica’s safe haven @ west 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 HK$1,065
HK$2,630 total
includes taxes & fees
19 Nov - 20 Nov
Angelica’s safe haven @ west haven
Fridge, microwave, oven, dishwasher
Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton
9.8 out of 10, Exceptional, (34)
"This old colonial home was very charming. We enjoyed our stay. The only thing to be aware of is there is only air conditioning in 4 of the bedrooms and it was quite hot while we were there. The location is great, and it's a short walk in to town."
United States
LauraLee E.
Large Charming Historic House close to Beaches
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Waterfront Cottage in Branford

Waterfront Cottage in Branford

branford
10.0 out of 10, Exceptional, (97)
"Host was wonderful to work with. House is amazing. Very spacious, beds were 5 Star hotel worthy!The location and view were spectacular. This was a perfect location and checked off ALL the boxes. "
United States
Kelly C.
Waterfront Cottage in Branford
On the beach, sun-loungers, beach towels
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Milford
10.0 out of 10, Exceptional, (131)
"Fantastic large rambling house perfect for having a family reunion. The location is fantastic as it is right across the street from the beach. Our host Debbie was very responsive and gracious. We would definitely stay here again!"
United States
Sion H.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Beach
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

2.0 star property
Westbrook Center
10.0 out of 10, Exceptional, (9)
"We had a great stay at the beach house! Luanne was a super-responsive host and communication with her throughout the stay through the app was a breeze. "
United States
Virgil C.
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!
Outdoor dining
Charming 3 Bedroom Beach Front Cottage

Charming 3 Bedroom Beach Front Cottage

2.0 star property
Milford
10.0 out of 10, Exceptional, (4)
"Stayed here while attending the Soundside Fest. Perfect location to be away from the busy Bridgeport area. The water is right there and it’s the perfect space for a weekend get away."
United States
Sarah W.
Charming 3 Bedroom Beach Front Cottage
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"All good"
Monica 1-night trip
Posted 2 days ago
Best Western Executive Hotel Of New Haven - West Haven

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