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

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Thimble Islands B&B

The Captain Stannard
Cozy up by the fireplace in this stylish living room, featuring a comfortable sofa, armchair, and decorative artwork.

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (237)
"Everything was fantastic, will stay again!"
The price is CA $244
CA $271 total
includes taxes & fees
Sep 3 - Sep 4
The Captain Stannard
The Homestead
Relax in a spacious room with a large bed, seating area, and cozy fireplace.

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (82)
"Best breakfast. The little things that were provided (warm bathroom towels, comfortable bed, patio outside our room just for us to enjoy) added to our wonderful 3 day get away in Madison. Don't want to forget the freshly made popcorn in the evening we so enjoyed. "
The Homestead
Jay's Ranch
Relax by the pool in a tranquil oasis, where a warm welcome awaits.

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 $158 total
includes taxes & fees
Aug 7 - Aug 8
Jay's Ranch
Westbrook Inn B&B
Relax in the serene outdoor patio area, surrounded by lush greenery and comfortable seating options.

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (155)
"My granddaughter and I had a lovely stay."
The price is CA $284
CA $315 total
includes taxes & fees
Sep 2 - Sep 3
Westbrook Inn B&B
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Backyard with a gravel surface, wooden deck, and small shed, surrounded by a fence.

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

The price is CA $868
CA $1,335 total
includes taxes & fees
Aug 7 - Aug 8
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Thimble Islands Bed & Breakfast
Enjoy a romantic dinner for two on the balcony overlooking the water.

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
"A beautiful, quiet home in a stunning setting run by two extremely gracious hosts. Breakfast on both days was excellent."
Thimble Islands Bed & Breakfast
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

Courtyard by Marriott New Haven Orange-Milford

Courtyard by Marriott New Haven Orange-Milford

10/10 Excellent
"Comfortable "
Jewel 1-night trip
Posted 2 days ago
Courtyard by Marriott New Haven Orange-Milford

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.