Find a Bed and Breakfast in Thimble Islands from CA $108

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Thimble Islands B&B

The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (238)
"Everything was fantastic, will stay again!"
The price is CA $245
CA $272 total
includes taxes & fees
Sep 8 - Sep 9
The Captain Stannard
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (157)
"Charming, beautiful inn; excellent food and service."
The price is CA $284
CA $316 total
includes taxes & fees
Sep 2 - Sep 3
Westbrook Inn B&B
The Homestead
Room, 1 King Bed, Patio, Ground Floor (7)

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (83)
"This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!"
The price is CA $466
CA $518 total
includes taxes & fees
Aug 20 - Aug 21
The Homestead
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Property grounds

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

The price is CA $871
CA $1,326 total
includes taxes & fees
Aug 18 - Aug 19
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Jay's Ranch
Exterior

Jay's Ranch

4.0 star property
7.6 out of 10, Good, (44)
"This was an amazing stay. Renee is a great host. She is clean, personable, and professional. The home is very cozy, and while still a work in progress, the outdoor area is beautiful and teeming with potential. This is not a hotel or a motel, understanding this, do not expect the starchy atmosphere of those places, but instead appreciate the friendly, homely vibe. If you’re looking for somewhere reasonably priced, clean, and cozy, this is a great spot."
The price is CA $108
CA $159 total
includes taxes & fees
Aug 24 - Aug 25
Jay's Ranch
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

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

10/10 Excellent
"Staff, view, parking, cleanliness. All 1000/1000. Keep coming back because it's awesome here."
John 1-night trip
Posted 2 days ago
Hyatt Place Milford / New Haven

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 CA $108 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 and 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.