Title: Thimble Islands B&B: Find the Best Bed and Breakfast | 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 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 [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) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-01-02&endDate=2026-01-04&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) ![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) ![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) ### The Captain Stannard Westbrook Center 9.6/10 Exceptional (255) "Clean, friendly and delicious continental breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miriam [](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) ![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) ![Suite](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/865dda17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Clinton Room](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/6c9c9c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westbrook Inn B&B Westbrook Center 9.8/10 Exceptional (174) "Beautiful place and wonderful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca CA $297 CA $330 total includes taxes & fees Nov 11 - Nov 12 [](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/f87cac33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![36-inch Smart TV with cable channels, TV, Netflix](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/6b4787fc.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) ### 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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $421 CA $467 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Old-Saybrook-Hotels-The-Homestead.h31958886.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/ecd1ecf3.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/cb2d285a.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 $889 CA $1,377 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Hamden-Hotels-2500-SF-Loft-You-Own-Full-Floor-Luxury-Oasis-In-A-Commercial-Space.h101878830.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=2025-11-21&endDate=2025-11-22®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 ![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 "TJ was awesome. Very nice, professional and courteous. Great check in process and genuinely nice person. Thanks TJ!" [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Hampton Inn by Hilton Shelton](//images.trvl-media.com/lodging/1000000/210000/200400/200381/e6ef0843_y.jpg) ### Hampton Inn by Hilton Shelton 10/10 Excellent "Convenient to Yale New Haven hospital. Nice room layout. Red Barn restaurant nearby great food and cocktails. Great breakfast at hotel" [](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.Hotel-Information) ![Cambria Hotel New Haven University Area](//images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg) ### Cambria Hotel New Haven University Area 10/10 Excellent "Great hotel. The WiFi didn’t work well but all else was great. " [](https://expedia.ca/New-Haven-Hotels-Cambria-Hotel-New-Haven-University-Area.h78614483.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 "." [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Motel 6 Milford, CT](//images.trvl-media.com/lodging/1000000/10000/300/291/5125a116_y.jpg) ### Motel 6 Milford, CT 10/10 Excellent "Laundry service is great " [](https://expedia.ca/New-Haven-Hotels-Motel-6-Milford.h291.Hotel-Information) ![Hotel Marcel New Haven, Tapestry Collection By Hilton](//images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/1699c03c_y.jpg) ### Hotel Marcel New Haven, Tapestry Collection By Hilton 10/10 Excellent "All of it " [](https://expedia.ca/New-Haven-Hotels-Hotel-Marcel-New-Haven.h71427300.Hotel-Information) ![Courtyard New Haven at Yale](//images.trvl-media.com/lodging/1000000/30000/25300/25273/89078fdd_y.jpg) ### Courtyard New Haven at Yale 10/10 Excellent "The staff was amazing. Especially want to call out Andrew at the front desk, Terrance the maintenance person, and I think the late night front desk person’s name was Tanisha. They were all very friendly and helpful. We had an issue with the heat and Terrance came up immediately later at night and fixed it within minutes! " [](https://expedia.ca/New-Haven-Hotels-Courtyard-New-Haven-At-Yale.h25273.Hotel-Information) ![The Blake Hotel](//images.trvl-media.com/lodging/33000000/32130000/32129700/32129620/95723c61_y.jpg) ### The Blake Hotel 10/10 Excellent "We’ve stayed at the Blake at least three times, and the facility is always nicely kept up. It’s convenient to be able to walk to Yale as well as all the shops and restaurants that New Haven has to offer. Parking is hit or miss and the rooms can be noisy on the weekend." [](https://expedia.ca/New-Haven-Hotels-The-Blake-Hotel.h32129620.Hotel-Information) ![Hilton Garden Inn Shelton](//images.trvl-media.com/lodging/1000000/290000/287700/287687/18ff21f4_y.jpg) ### Hilton Garden Inn Shelton 10/10 Excellent "The room was very clean. It was a great stay." [](https://expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Shelton.h287687.Hotel-Information) ## Find out more about Thimble Islands ## Thimble Islands B&B information | Number of reviews | | | --- | --- | | Accommodation | B&B | | Lowest Price | | | Highest Price | | ## 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 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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