Title: Chilmark Vacation Packages & Trips 2026 from CA $1,825 | Expedia.ca [Hotels in Chilmark](https://expedia.ca/Chilmark-Hotels.d6135676.Travel-Guide-Hotels)[Vacation Rentals in Chilmark](https://expedia.ca/Chilmark-Vacation-Rentals.d6135676.Travel-Guide-VacationRentals)[Things to do in Chilmark](https://expedia.ca/Things-To-Do-In-Chilmark.d6135676.Travel-Guide-Activities)[Chilmark Car Rentals](https://expedia.ca/Car-Rentals-In-Chilmark.d6135676.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6135676/824050a0-a336-4250-9bcd-66c115369156.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chilmark Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Chilmark Vacation With a reputation for its unspoiled nature and spectacular views, Chilmark is a perfect getaway destination. Book one of our Chilmark vacation packages and enjoy all that this fascinating city has to offer. If a sightseeing tour is on the agenda during your trip to Chilmark, look around major attractions like [Aquinnah Cliffs](https://www.expedia.ca/Aquinnah-Cliffs-Aquinnah.d6091789.Vacation-Attraction), [Gay Head Lighthouse](https://www.expedia.ca/Gay-Head-Lighthouse-Aquinnah.d6091787.Vacation-Attraction) and [Menemsha Beach](https://www.expedia.ca/Menemsha-Beach-Chilmark.d6287512.Vacation-Attraction). No matter your travel plans or the size of your budget, putting together the ultimate tailored Chilmark vacation is a cinch with Expedia. ## Top Chilmark Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Morgan Hotel](https://images.trvl-media.com/lodging/40000000/39210000/39201700/39201680/f4565200_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Morgan Hotel CA $1,825 per person Jun 7 - Jun 14 found 1 day ago Roundtrip flight included Toronto (YYZ) to Vineyard Haven (MVY) 8.4/10 Very Good! (207 reviews) Wonderful hotel in the heart of Oak Bluffs. Minutes to the Inkwell and the Circuit Ave strip. Great place to spend a quick weekend getaway. Reviewed on Mar 21, 2026 ![Vineyard Harbor Motel - Private Beach](https://images.trvl-media.com/lodging/61000000/60390000/60384600/60384563/71c0b2e0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Vineyard Harbor Motel - Private Beach CA $1,994 per person Jun 7 - Jun 14 found 1 day ago Roundtrip flight included Toronto (YYZ) to Vineyard Haven (MVY) 9/10 Wonderful! (621 reviews) Perfect stay, very friendly staff. love it Reviewed on Mar 24, 2026 ![Harbor View Hotel](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/d518b4f4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Harbor View Hotel CA $7,727 per person Jun 7 - Jun 14 found 1 day ago Roundtrip flight included Toronto (YYZ) to Vineyard Haven (MVY) 8.8/10 Excellent! (1,000 reviews) Exception staff, Madison was amazing! Reviewed on Mar 12, 2026 ![Faraway Martha's Vineyard](https://images.trvl-media.com/lodging/1000000/70000/65700/65623/7a38c33e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Faraway Martha's Vineyard CA $3,537 per person Jun 7 - Jun 14 found 1 day ago Roundtrip flight included Toronto (YYZ) to Vineyard Haven (MVY) 9/10 Wonderful! (1,000 reviews) Very cozy comfortable hotel!! Reviewed on Dec 17, 2025 ### Chilmark Beach Vacation Whether you're traveling solo or with the whole gang, it'll be easy to find rest and relaxation on your Chilmark vacation. Search around for shiny rocks and shells or simply sit and watch the sunset. Whatever you choose to do, your trip to Chilmark will certainly be memorable. Lucy Vincent Beach, located 2 kilometres from the town center, is perfect for those after convenience. Many visitors also lock in Chilmark vacation packages closer to Menemsha Beach, another great nearby option. ## Ready to book your vacation to Chilmark? Choose your dates ## Chilmark Hotel Deals ![Iris Hotel Cape Cod ](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/fe097a20_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Iris Hotel Cape Cod 291 Jones Rd Falmouth MA Fully refundableReserve now, pay when you stay CA $136 CA $156 total Apr 1 - Apr 2 includes taxes & fees 8.6/10 Excellent! (198 reviews) The hotel was comfortable. The breakfast was decent. Areas were clean. The walls are VERY thin—- you can hear what’s going on in the other room. Free parking and free breakfast were the biggest draws. Reviewed on Mar 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=11989&PinnedHotelID=11989&HadPinnedHotel=true®ionId=6135676) ![Falmouth Inn](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/a26689a2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Falmouth Inn 824 Main Street Falmouth MA Fully refundableReserve now, pay when you stay CA $135 CA $183 total Apr 23 - Apr 24 includes taxes & fees 8/10 Very Good! (1,000 reviews) Was as double queen bed room, it was clean. Shower had decent pressure and heat. Staff were very friendly as well. Reviewed on Mar 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F04%2F2026&endDate=24%2F04%2F2026&selected=893142&PinnedHotelID=893142&HadPinnedHotel=true®ionId=6135676) ![Hampton Inn by Hilton New Bedford/Fairhaven](https://images.trvl-media.com/lodging/1000000/60000/55000/54948/9bfe4d46_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn by Hilton New Bedford/Fairhaven 1 Hampton Way Fairhaven MA Fully refundableReserve now, pay when you stay CA $163 CA $182 total Apr 2 - Apr 3 includes taxes & fees 8.8/10 Excellent! (1,002 reviews) Everything was great and I will see you again next year. Reviewed on Mar 14, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F04%2F2026&endDate=03%2F04%2F2026&selected=54948&PinnedHotelID=54948&HadPinnedHotel=true®ionId=6135676) [See all 2,175 properties in Chilmark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026®ionId=6135676) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### What to do in Chilmark ![Martha's Vineyard Self-Driving Audio Tour](https://mediaim.expedia.com/localexpert/5102813/025d1ec3-9f51-490a-a663-49c6883332e8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Martha's Vineyard: Self-Guided Driving Audio Tour CA $18 per traveller [](https://expedia.ca/things-to-do/marthas-vineyard-self-guided-driving-audio-tour.a5102813.activity-details) ![Massachusetts Self-Guided Driving and Walking Tours Bundle](https://mediaim.expedia.com/localexpert/5280486/e51020c2-3f21-4b6a-ae0a-93b340f5a0f4.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Massachusetts: Smartphone-Based Audio Tour Bundle CA $62 per traveller [](https://expedia.ca/things-to-do/massachusetts-smartphone-based-audio-tour-bundle.a5280486.activity-details) ![Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours](https://mediaim.expedia.com/localexpert/5247794/0163ce8b-bcb9-433e-bb84-fa4c7a677dc8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours CA $68 per adult [](https://expedia.ca/things-to-do/massachusetts-self-guided-audio-tour-bundle-10-tours.a5247794.activity-details) [See all activities in Chilmark](https://expedia.ca/things-to-do/search?rid=6135676) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app