Title: 20 Best B&B in Chilmark, MA - Bed and Breakfast from $145 | Expedia.com [Chilmark Travel Guide](https://expedia.com/Chilmark.dx6135676)[Hotels in Chilmark](https://expedia.com/Chilmark-Hotels.d6135676.Travel-Guide-Hotels)[Vacation Rentals in Chilmark](https://expedia.com/Chilmark-Vacation-Rentals.d6135676.Travel-Guide-VacationRentals)[Flights to Chilmark](https://expedia.com/Cheap-Flights-To-Chilmark.d6135676.Travel-Guide-Flights)[Things to do in Chilmark](https://expedia.com/Things-To-Do-In-Chilmark.d6135676.Travel-Guide-Activities)[Car Rentals in Chilmark](https://expedia.com/Car-Rentals-In-Chilmark.d6135676.Car-Rental-Guide)[Chilmark Vacation Packages](https://expedia.com/Chilmark.d6135676.Destination-Travel-Guides) ![Chilmark Shellfish Department on Martha’s Vineyard](https://images.trvl-media.com/place/6135676/824050a0-a336-4250-9bcd-66c115369156.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6135676/824050a0-a336-4250-9bcd-66c115369156.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6135676&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6135676&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6135676&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6135676&startDate=2026-05-01&endDate=2026-05-03&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chilmark bed & breakfast ![Exterior](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/642c704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/216d8c41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/e7d27f51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/3d82ccd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Frederick William House [](https://www.expedia.com/Falmouth-Hotels-Frederick-William-House.h14844940.Hotel-Information) Falmouth 9.6/10 Exceptional (298 reviews) "Beat B&B i have ever stayed at! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip $130 nightly $149 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Falmouth-Hotels-Frederick-William-House.h14844940.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2800000/2796200/2796134/0678b292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/3000000/2800000/2796200/2796134/26470c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2800000/2796200/2796134/1678d73c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2800000/2796200/2796134/34cdb618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delano Homestead Bed & Breakfast [](https://www.expedia.com/Fairhaven-Hotels-Delano-Homestead-Bed-Breakfast.h2796134.Hotel-Information) Fairhaven 9.6/10 Exceptional (163 reviews) "It was a wonderful stay. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hye-Won $130 nightly $145 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Fairhaven-Hotels-Delano-Homestead-Bed-Breakfast.h2796134.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/7000000/6980000/6976600/6976506/308675cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/7000000/6980000/6976600/6976506/5beb251a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/7000000/6980000/6976600/6976506/c52ea891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6980000/6976600/6976506/c5e285e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Palmer House Inn [](https://www.expedia.com/Falmouth-Hotels-The-Palmer-House-Inn.h6976506.Hotel-Information) Falmouth 9.6/10 Exceptional (175 reviews) "Nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian $239 nightly $273 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Falmouth-Hotels-The-Palmer-House-Inn.h6976506.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/23000000/22810000/22802900/22802884/4318521e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, 1 King Bed, Balcony, Ocean View | Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/23000000/22810000/22802900/22802884/198933dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/23000000/22810000/22802900/22802884/2fd5629c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Double Room, 1 King Bed, Balcony, Ocean View | Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/23000000/22810000/22802900/22802884/3ceef1f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn on the Sound [](https://www.expedia.com/Falmouth-Hotels-Inn-On-The-Sound.h22802884.Hotel-Information) Falmouth Heights 9.8/10 Exceptional (212 reviews) "Quiet, charming, nice breakfast, right across from beach" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bruce $269 nightly $308 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Falmouth-Hotels-Inn-On-The-Sound.h22802884.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.com/Hotel-Search?startDate=2026-03-21&endDate=2026-03-22®ionId=6135676&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_6135676) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChilmark-Bed-And-Breakfast.d6135676-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChilmark-Bed-And-Breakfast.d6135676-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Chilmark Hotel Reviews ![Hampton Inn by Hilton New Bedford/Fairhaven](https://images.trvl-media.com/lodging/1000000/60000/55000/54948/9bfe4d46_y.jpg) ### Hampton Inn by Hilton New Bedford/Fairhaven 10/10 Excellent "Nice place" [](https://expedia.com/Fairhaven-Hotels-Hampton-Inn-By-Hilton-New-BedfordFairhaven.h54948.Hotel-Information) ![Iris Hotel Cape Cod ](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/fe097a20_y.jpg) ### Iris Hotel Cape Cod 8/10 Good "Good breakfast soft beds" [](https://expedia.com/Falmouth-Hotels-Hotel-Cape-Cod.h11989.Hotel-Information) ![The Franklin Hotel Martha's Vineyard](https://images.trvl-media.com/lodging/77000000/76640000/76637400/76637391/0219cce7_y.jpg) ### The Franklin Hotel Martha's Vineyard 10/10 Excellent "Very beautiful hotel. Feels like home. Very well designed! Very comfy.. my go to on vineyard" [](https://expedia.com/Edgartown-Hotels-The-Franklin-Hotel-Marthas-Vineyard.h76637391.Hotel-Information) ![The Coonamessett](https://images.trvl-media.com/lodging/7000000/6600000/6591200/6591194/b324630a_y.jpg) ### The Coonamessett 10/10 Excellent "Staff was very helpful ! We were arriving late with alot of luggage, lots of snow on the ground and seniors. They arranged a room right next to the entrance will a well shoveled path. Checked in with us as well" [](https://expedia.com/Falmouth-Hotels-The-Coonamessett.h6591194.Hotel-Information) ![Vineyard Harbor Motel - Private Beach](https://images.trvl-media.com/lodging/61000000/60390000/60384600/60384563/71c0b2e0_y.jpg) ### Vineyard Harbor Motel - Private Beach 10/10 Excellent "Room spotless . Bed super comfortable. Staff nice and made me feel as if I were just back from a trip away!! What’s not to love!!" [](https://expedia.com/Vineyard-Haven-Hotels-Vineyard-Harbor-Motel.h60384563.Hotel-Information) ![The Club at New Seabury](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/d67fc379_y.jpg) ### The Club at New Seabury 10/10 Excellent "Accommodations were spacious and clean. We enjoyed our stay so much we extended our stay. Check in was helpful, kind and went out of their way for us as we were away celebrating our birthdays! We hope to return again soon. " [](https://expedia.com/Mashpee-Hotels-The-Club-At-New-Seabury.h11621632.Hotel-Information) ![Sea Crest Beach Resort](https://images.trvl-media.com/lodging/1000000/30000/25600/25567/024e668f_y.jpg) ### Sea Crest Beach Resort 2/10 Terrible "Dirty, run down rooms in a dungeoness part of the hotel. Unacceptable for a place that represents and charges as a top cape cod hotel. The front desk management/staff wasn't very pleasant/helpful either." [](https://expedia.com/North-Falmouth-Hotels-Sea-Crest-Beach-Hotel.h25567.Hotel-Information) ![Admiralty Inn & Suites - a Red Collection Hotel](https://images.trvl-media.com/lodging/2000000/1280000/1279900/1279850/ccfd7232_y.jpg) ### Admiralty Inn & Suites - a Red Collection Hotel 10/10 Excellent "Excellent everything so nicely " [](https://expedia.com/Falmouth-Hotels-Admiralty-Inn-Suites.h1279850.Hotel-Information) ![Mansion House Inn And Spa](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/04588712_y.jpg) ### Mansion House Inn And Spa 10/10 Excellent "Clean room, professional staff, comfortable bed, spaciousness. I do wish that the bath was functional. We could only shower. A very pleasant stay and we would come again." [](https://expedia.com/Vineyard-Haven-Hotels-Mansion-House-Inn-And-Spa.h2182094.Hotel-Information) ## Find out more about Chilmark ## Chilmark B&B information | Number of reviews | 848 | | ----------------- | ------ | | Accommodation | 12 B&B | | Lowest Price | $145 | | Highest Price | $308 | ## Frequently asked questions ### What is the nightly rate for a Bed & Breakfast in Chilmark? ### When is the best time to book a Bed and Breakfast in Chilmark? > During July, expect warm temperatures averaging in the mid-70s to low 80s Fahrenheit, creating an inviting environment for swimming, sailing, and exploring the charming coastal town. This lively season attracts families, couples, and adventure seekers who relish the rich atmosphere filled with art, music, and culinary delights. > > > For those looking to travel on a budget, consider visiting in October. This month provides a quieter experience, with milder temperatures and the chance to witness the beautiful fall foliage that transforms the island's landscape. It's a great opportunity for leisurely strolls along the beach or exploring the local art galleries without the summer crowds. ### What is the difference between a Chilmark Bed and Breakfast and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near Chilmark Chocolates ](https://www.expedia.com/Chilmark-Chocolates-Hotels.0-l553248621532666149-0.Travel-Guide-Filter-Hotels) - [B&B in Menemsha ](https://www.expedia.com/Menemsha-Bed-And-Breakfast.d6060685-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Menemsha ](https://www.expedia.com/Menemsha-Cottages.d6060685-aaCottages.Travel-Guide-Accommodation) - [Hostels in Menemsha ](https://www.expedia.com/Menemsha-Hostels.d6060685-aaHostels.Travel-Guide-Accommodation) - [Vacation Homes in Menemsha ](https://www.expedia.com/Menemsha-Private-Vacation-Homes.d6060685-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Condo Resorts in Menemsha ](https://www.expedia.com/Menemsha-Condominium-Resort.d6060685-aaCondominiumResort.Travel-Guide-Accommodation) - 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