Title: Thimble Islands B&B: Find the Best Bed and Breakfast from CA $159 | Expedia.ca [Thimble Islands Travel Guide](https://expedia.ca/Thimble-Islands.dx6341069)[Hotels in Thimble Islands](https://expedia.ca/Thimble-Islands-Hotels.d6341069.Travel-Guide-Hotels)[Vacation Rentals in Thimble Islands](https://expedia.ca/Thimble-Islands-Vacation-Rentals.d6341069.Travel-Guide-VacationRentals)[Flights to Thimble Islands](https://expedia.ca/Cheap-Flights-To-Thimble-Islands.d6341069.Travel-Guide-Flights)[Thimble Islands Car Rentals](https://expedia.ca/Car-Rentals-In-Thimble-Islands.d6341069.Car-Rental-Guide)[Thimble Islands Vacation Packages](https://expedia.ca/Thimble-Islands.d6341069.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find a Bed and Breakfast in Thimble Islands from CA $159 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-09-26&endDate=2025-09-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-10-03&endDate=2025-10-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Thimble Islands B&B ![IPod dock, MP3 dock](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/497076d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Bedroom, Private Bathroom](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/bce7c7c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/7506bfd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/ab015163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Captain Stannard Westbrook Center 9.6/10 Exceptional (247) "Everything was fantastic, will stay again!" CA $284 CA $316 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Westbrook-Hotels-Captain-Stannard-BB-Country-Inn.h1479959.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/46915263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/22d95002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/865dda17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/f2c9a8ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westbrook Inn B&B Westbrook Center 9.8/10 Exceptional (167) "Beautiful place and wonderful staff" CA $294 CA $327 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Old-Saybrook-Hotels-Westbrook-Inn-Bed-And-Breakfast.h35596310.Hotel-Information) ![Room, 1 King Bed, Patio, Ground Floor (7)](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/c76f25a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/90437a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/5ee4b9df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional House | Living area](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/e8c6bce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Homestead Madison Center 10/10 Exceptional (87) "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!" CA $447 CA $496 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Old-Saybrook-Hotels-The-Homestead.h31958886.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93140000/93133100/93133074/190efae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/94000000/93140000/93133100/93133074/79349d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business Room | Living area](https://images.trvl-media.com/lodging/94000000/93140000/93133100/93133074/012f1989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/94000000/93140000/93133100/93133074/6f34105d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jay's Ranch Hamden 7.6/10 Good (45) "Im so happy I found this place to stay. Meets all my needs and great service !!" CA $108 CA $159 total includes taxes & fees Sep 22 - Sep 23 [](https://www.expedia.ca/Hamden-Hotels-Jays-Ranch.h93133074.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/056c3b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/cb2d285a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/5aa07695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/e5e2d941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space Hamden CA $868 CA $1,336 total includes taxes & fees Sep 22 - Sep 23 [](https://www.expedia.ca/Hamden-Hotels-2500-SF-Loft-You-Own-Full-Floor-Luxury-Oasis-In-A-Commercial-Space.h101878830.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/35000000/34510000/34508300/34508249/9d8b7b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Heron Room | Water view](https://images.trvl-media.com/lodging/35000000/34510000/34508300/34508249/3ff621d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/35000000/34510000/34508300/34508249/d236b95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34510000/34508300/34508249/72380bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Thimble Islands Bed & Breakfast Branford 10/10 Exceptional (4) "A beautiful, quiet home in a stunning setting run by two extremely gracious hosts. Breakfast on both days was excellent." [](https://www.expedia.ca/New-Haven-Hotels-Thimble-Islands-Bed-Breakfast.h34508249.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-05&endDate=2025-10-06®ionId=6341069&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FThimble-Islands-Bed-And-Breakfast.d6341069-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FThimble-Islands-Bed-And-Breakfast.d6341069-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Thimble Islands Hotel Reviews ![Red Roof Inn Meriden](//images.trvl-media.com/lodging/1000000/10000/2900/2831/05873179_y.jpg) ### Red Roof Inn Meriden 10/10 Excellent "Management really care about this hotel Is a simple and cheap hotel but you can tell they people running the place they do care and do the best with what they have " [](https://expedia.ca/Hartford-Hotels-Red-Roof-Inn-Meriden.h2831.Hotel-Information) ![Best Western Executive Hotel Of New Haven - West Haven](//images.trvl-media.com/lodging/1000000/30000/23300/23217/b63e42e2_y.jpg) ### Best Western Executive Hotel Of New Haven - West Haven 10/10 Excellent "Clean room, kind of worn but totally fine for a night" [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Omni New Haven Hotel at Yale](//images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg) ### Omni New Haven Hotel at Yale 10/10 Excellent "Caring Staff + Great Location = Happy Yale Parents We had a great four-night stay while moving our daughter into Yale. The managers truly went above and beyond. At check-in, one manager patiently showed us alternative room options when we were worried about noise, and the room we chose was perfect. Another manager impressed us as well — after we mentioned the tub was slippery and no mat had arrived, he personally went out to buy one for us. The location is unbeatable for visiting Yale, and we loved being able to walk everywhere. The afternoon snacks in the lobby were a nice touch as well. Housekeeping could improve on restocking supplies like coffee pods and coffee cups, but calls to the front desk resolved it quickly. The surrounding neighborhood isn’t the best, though that’s not the hotel’s fault. Overall, excellent service and an ideal location made this a very positive stay. We’d happily return." [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg) ### New Haven Hotel 10/10 Excellent "Very walkable" [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Hamden Hotel and Suites – Hamden New Haven](//images.trvl-media.com/lodging/1000000/20000/18000/17931/c3c836db_y.jpg) ### Hamden Hotel and Suites – Hamden New Haven 10/10 Excellent "νονε" [](https://expedia.ca/New-Haven-Hotels-Clarion-Hotel-Suites-Hamden-New-Haven.h17931.Hotel-Information) ![Holiday Inn Express & Suites Milford by IHG](//images.trvl-media.com/lodging/1000000/10000/3900/3900/f87dad0a_y.jpg) ### Holiday Inn Express & Suites Milford by IHG 10/10 Excellent "This hotel is a good version of standard issue with an above-average breakfast and an attractive indoor pool. It is hard to find at night and could use a light on the sign at the entrance. There is a brightly lit Hilton across the road, and Waze doesn't make clear where the Holiday Inn is, so I wasted time trying to check into the wrong hotel." [](https://expedia.ca/New-Haven-Hotels-Holiday-Inn-Express-Suites-Milford.h3900.Hotel-Information) ![Hyatt Place Milford / New Haven](//images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent "Bulbs in the elevator need replacing " [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Clarion Inn](//images.trvl-media.com/lodging/1000000/10000/7600/7519/36377da0_y.jpg) ### Clarion Inn 10/10 Excellent "great " [](https://expedia.ca/North-Haven-Hotels-Clarion-Inn.h7519.Hotel-Information) ![Hampton Inn Milford](//images.trvl-media.com/lodging/1000000/20000/13100/13007/58bf94a8_y.jpg) ### Hampton Inn Milford 10/10 Excellent "Terrific staff. Great facility." [](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-Milford.h13007.Hotel-Information) ## Find out more about Thimble Islands ## Thimble Islands B&B information | Number of reviews | 537 | | --- | --- | | Accommodation | 6 B&B | | Lowest Price | CA $159 | | Highest Price | CA $1,336 | ## 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 $159 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. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Guilford](https://www.expedia.ca/4Star-Guilford-Hotels.s40-0-d183062.Travel-Guide-Filter-Hotels) - [Hotels near Bill Miller’s Castle](https://www.expedia.ca/Bill-Millers-Castle-Hotels.0-l553248621563220905-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Branford](https://www.expedia.ca/Branford-Apart-Hotels.d6243-aaApartHotels.Travel-Guide-Accommodation) - [Apartments in Branford](https://www.expedia.ca/Branford-Apartments.d6243-aaApartments.Travel-Guide-Accommodation) - [B&B in Branford](https://www.expedia.ca/Branford-Bed-And-Breakfast.d6243-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Boutique Hotels in Branford Center](https://www.expedia.ca/Branford-Center-Branford-Hotels-Boutique-Hotel.0-n6348199-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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