Holiday Homes in Thimble Islands

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Check prices for these dates

Next weekend
26 Sept - 28 Sept
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

Featured Holiday Homes in Thimble Islands and around

Our top choices for Thimble Islands holiday homes

Cozy 2 bedroom home located minutes from downtown
Interior

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (29)
"A very comfortable short stay in a convenient location"
Cozy 2 bedroom home located minutes from downtown
McAngel Haven: 5 mins from Yale
Fridge, microwave, oven, stovetop

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (14)
"My family and I stayed at the property for a wedding in Milford. The house had plenty of space for our group to say, and the bedrooms were comfortable. The three bathrooms were helpful for our group to efficiently get ready for the wedding, and the kitchen was adequately appointed for us to have meals."
The price is €476
includes taxes & fees
22 Oct - 23 Oct
McAngel Haven: 5 mins from Yale
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Beach nearby

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

9.4 out of 10, Exceptional, (14)
"This Carriage House is exactly as described. Wonderful location and setting, just steps away from Branford Point. Hope to visit again soon! "
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
New Madison beach house - Ocean front- Great views- booking Summer 2025
Exterior

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (66)
"Owner was great to work with and very responsive. House is in a great location. "
New Madison beach house - Ocean front- Great views- booking Summer 2025
Ranch style living at its best with country garden & patio!
Exterior

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (14)
"Solid location and quiet neighborhood good after a long day."
Ranch style living at its best with country garden & patio!
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Dining

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

9.8 out of 10, Exceptional, (67)
"Great family get together where we all were very comfortable. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
On the beach, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (127)
"Fantastic all around!"
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Charming beach home, complete with pool & cozy guest house!
Interior

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

9.8 out of 10, Exceptional, (33)
"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!
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!
Beach

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

2.0 star property
10.0 out of 10, Exceptional, (6)
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!
Amazing Lakefront Property
Interior

Amazing Lakefront Property

9.8 out of 10, Exceptional, (26)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property
Clear LI Sound waterview, Wedding pics, Yale&Beach
Smart TV, books

Clear LI Sound waterview, Wedding pics, Yale&Beach

10.0 out of 10, Exceptional, (7)
"Attended a wedding close by. This house was a comfortable clean place to rest in between events. Lovely water front. Calm and peaceful"
The price is €532
includes taxes & fees
22 Sept - 23 Sept
Clear LI Sound waterview, Wedding pics, Yale&Beach
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Beach nearby, sun-loungers, beach towels

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (48)
"Absolutely, beautiful and great hostess"
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Minutes to Walnut Beach, newly renovated 3 bedroom home
Sun-loungers, beach towels

Minutes to Walnut Beach, newly renovated 3 bedroom home

9.6 out of 10, Exceptional, (10)
"This house was perfect for our visit. It was clean and comfortable and provided everything we needed. Walking distance to a restaurant, coffee shop and the best ice cream! Would definitely stay here again. "
Minutes to Walnut Beach, newly renovated 3 bedroom home
Storybook Cottage
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Storybook Cottage

10.0 out of 10, Exceptional, (2)
"Charming antique property full of character with private backyard, minutes to everything in Old Saybrook. Note- bedrooms half bath are upstairs along with lovely family room, full bath with shower is down. Property was clean and comfortable. We enjoyed our stay!"
Storybook Cottage
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Beach nearby, sun-loungers, beach towels

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

9.8 out of 10, Exceptional, (6)
"It was just what we needed!The colors and layout was calming, welcoming an relaxing. A wonderful getaway from a stressful life. Harvey Beach was the cherry on top!"
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
🌾Welcoming Tiny Home! Downtown & Beachy☀️
Terrace/patio

🌾Welcoming Tiny Home! Downtown & Beachy☀️

9.8 out of 10, Exceptional, (15)
"The owner knows how to create a welcoming feel and comfortable vibe! This listing is excellent - thank you Stacey! "
🌾Welcoming Tiny Home! Downtown & Beachy☀️
#37 - Luxury Collection
Property grounds

#37 - Luxury Collection

2.0 star property
8.8 out of 10, Excellent, (3)
"We enjoyed the coziest getaway at this property. Newly renovated, clean and tucked away without being accessible to local attractions. "
The price is €343
includes taxes & fees
22 Sept - 23 Sept
#37 - Luxury Collection
3-bedroom house just walking distance from Yale and Downtown
Terrace/patio

3-bedroom house just walking distance from Yale and Downtown

The price is €356
includes taxes & fees
24 Sept - 25 Sept
3-bedroom house just walking distance from Yale and Downtown
Cozy East Haven Home • Near Beach & Yale
Microwave, oven, stovetop, dishwasher

Cozy East Haven Home • Near Beach & Yale

10.0 out of 10, Exceptional, (2)
"So comfy for the dog and I for a night. Just what we needed!"
Cozy East Haven Home • Near Beach & Yale
Coastal Retreat Waterfront, Deck, Awesome Views
Fridge, microwave, oven, stovetop

Coastal Retreat Waterfront, Deck, Awesome Views

10.0 out of 10, Exceptional, (18)
"Great place. Exceptional location. Great view with restaurants and recreation nearby. "
Coastal Retreat Waterfront, Deck, Awesome Views
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

Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

10/10 Excellent
"νονε"
Gyoung 2-night trip
Posted 3 days ago
Hamden Hotel and Suites – Hamden New Haven

Find out more about Thimble Islands

Find out more about Thimble Islands

Thimble Islands Holiday Homes information

Number of reviews
456
Accommodation
358 Holiday Homes
Lowest Price
€343
Highest Price
€532

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