Search Vacation Homes in Thimble Islands

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Vacation Homes in Thimble Islands

Our top choices for Thimble Islands vacation homes

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (29)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown

Cozy Home Near New Haven

10.0 out of 10, Exceptional, (1)
"So comfy for the dog and I for a night. Just what we needed!"
The price is ¥17,633
¥23,217 total
includes taxes & fees
Sep 9 - Sep 10
Cozy Home Near New Haven

Modern Beach Home - Waterview, close to restaurants, universities and hospitals

10.0 out of 10, Exceptional, (1)
"The check in process was very easy. The home was airy and bright. My family and I felt the peace and relaxation of the home. The kitchen was large and clean."
Modern Beach Home - Waterview, close to restaurants, universities and hospitals

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

10.0 out of 10, Exceptional, (124)
"We had a magical stay in this truly enchanting home the beds were comfortable. The kitchen well equipt for entertaining a large crowd. The fire place and piano were the backdrop for many intimate moments. The gardens were beautiful with azaleas and many perennials. The location directly across from the beach allowed for many walks and playtime together and the waves sung us to sleep at night. We would love to make a new family tradition for visiting here again and again."
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Beach Bungalow, walk to beach, private backyard

10.0 out of 10, Exceptional, (3)
"The property was perfect for all of us. It was in a quiet neighborhood and great location."
Beach Bungalow, walk to beach, private backyard

Charming beach home, complete with pool & cozy guest house!

9.8 out of 10, Exceptional, (31)
"It was very comfortable and cozy, a very great place to spend with your loved ones, very spacious and had everything we needed to enjoy our stay."
Charming beach home, complete with pool & cozy guest house!

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (66)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Family Gem on Dyer Street

The price is ¥61,627
¥135,818 total
includes taxes & fees
Aug 26 - Aug 27
Family Gem on Dyer Street

Historic Coastal Home • Marsh Views • Pet-Friendly

10.0 out of 10, Exceptional, (1)
"We had a wonderful weekend here!The host was very accommodating with check-in and check-out times. The house was beautiful, spotless and full of character. Lots of space for two families. The yard was really nice and much bigger than it seemed it the photos. We had a really great stay. "
Historic Coastal Home • Marsh Views • Pet-Friendly

Waterfront Estate Home - Beach and Shared Pool - East

9.8 out of 10, Exceptional, (43)
"Perfect home for a big family gathering!"
Waterfront Estate Home - Beach and Shared Pool - East

Cozy 3 bedroom minutes from Yale and the beach

8.0 out of 10, Very Good, (4)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach

The Beach Nest-Lux Cottage Steps to the Beach

9.8 out of 10, Exceptional, (6)
"This is exactly what we needed. Nice area, great place to walk, easy to relax. "
The Beach Nest-Lux Cottage Steps to the Beach

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

9.6 out of 10, Exceptional, (133)
"Very much enjoyed our trip! "
The price is ¥50,430
¥93,774 total
includes taxes & fees
Aug 26 - Aug 27
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

3-bedroom house just walking distance from Yale and Downtown

The price is ¥33,062
¥61,826 total
includes taxes & fees
Aug 26 - Aug 27
3-bedroom house just walking distance from Yale and Downtown

Guilford home -self check in, off-street parking

9.2 out of 10, Wonderful, (9)
"Nice house, manageable distance from beaches and restaurants "
Guilford home -self check in, off-street parking

Beach community with private beaches

10.0 out of 10, Exceptional, (12)
"We had a wonderful week staying here with my family. It was family friendly, clear, had everything we needed and was a 10 min walk from beach!"
Beach community with private beaches

McAngel Haven: 5 mins from Yale

9.4 out of 10, Exceptional, (13)
"Had a wonderful but short stay in New Haven. Home.of PEZ and PIZZA . "
The price is ¥33,723
¥77,868 total
includes taxes & fees
Aug 26 - Aug 27
McAngel Haven: 5 mins from Yale

Spacious 4-bedroom house with AC, WiFi in welcoming Guilford

10.0 out of 10, Exceptional, (2)
" The house was awesome, had an very good layout, great yard, nice deck and it was the perfect place for our group! Great communication with the owner!"
Spacious 4-bedroom house with AC, WiFi in welcoming Guilford

Walk to Beaches: Sunny East Haven Home w/ Grill

2.0 star property
10.0 out of 10, Exceptional, (6)
"The beds were so comfy. The shower was awesome. Everything was perfect"
Walk to Beaches: Sunny East Haven Home w/ Grill

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

10.0 out of 10, Exceptional, (12)
"The house was as advertised and located in a really quiet neighborhood. The host was easy to work with and responded to me each time I texted her. If the opportunity ever comes up again, we would definitely stay at this property again."
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Thimble Islands Hotel Reviews