Book Thimble Islands Bed & Breakfast

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Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Thimble Islands bed & breakfast

IPod dock, MP3 dock
The Captain Stannard

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (259)
"The Inn and staff were warm and welcoming, the facility exceptionally clean. Breakfast exceeded my expectations for a continental breakfast! Would absolutely stay again! "
United States
Lisa
$238 nightly
The price is $264
Dec 30 - Dec 31
Total with taxes and fees
The Captain Stannard
Fireplace
Westbrook Inn B&B

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (176)
"Charming, beautiful inn; excellent food and service."
United States
Michael
$206 nightly
The price is $229
Dec 22 - Dec 23
Total with taxes and fees
Westbrook Inn B&B
Room, 1 King Bed, Patio, Ground Floor (2) | Terrace/patio
The Homestead

The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (90)
"Beautiful property- wonderful staff- clean, comfortable and relaxed feeling with a lovely breakfast 😄"
United States
Anthony
$313 nightly
The price is $347
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Homestead
Interior
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Hamden
$863 nightly
The price is $976
Dec 22 - Dec 23
Total with taxes and fees
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
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

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Great hotel. Really nice reception person. Fast process. Nice room. I recommend fully with 5 stars + . "
Brian 1-night trip
Posted 2 days ago
New Haven Hotel

Find out more about Thimble Islands

Thimble Islands B&B information

Number of reviews
518
Accommodation
6 B&B
Lowest Price
$229
Highest Price
$976

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Thimble Islands?
Prices for B&Bs in Thimble Islands often vary, but you can find a great deal from $229 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Thimble Islands B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
What is the difference between a Thimble Islands Bed & Breakfast and a hotel?
Every Thimble Islands B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Thimble Islands B&Bs.

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