Title: Chilmark Vacation Packages & Trips 2026 from CA $719 | 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. ![Summercamp](https://images.trvl-media.com/lodging/11000000/10060000/10058600/10058501/4ff1c19a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Summercamp CA $719 per person Apr 25 - Apr 28 found 14 hours ago Roundtrip non-stop flight included Toronto (YTO) to Vineyard Haven (MVY) 9.2/10 Wonderful! (1,002 reviews) Lovely stay and the staff was friendly and helpful. Excellent location. Reviewed on Dec 17, 2025 ![Vineyard Harbor Motel - Private Beach](https://images.trvl-media.com/lodging/61000000/60390000/60384600/60384563/6bd7fc20_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Vineyard Harbor Motel - Private Beach CA $739 per person Apr 25 - Apr 28 found 14 hours ago Roundtrip non-stop flight included Toronto (YTO) to Vineyard Haven (MVY) 9/10 Wonderful! (605 reviews) Friendly staff, nice clean room Reviewed on Feb 6, 2026 ![The Franklin Hotel Martha's Vineyard](https://images.trvl-media.com/lodging/77000000/76640000/76637400/76637391/0e2e74e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Franklin Hotel Martha's Vineyard CA $769 per person Apr 25 - Apr 28 found 14 hours ago Roundtrip non-stop flight included Toronto (YTO) to Vineyard Haven (MVY) 9.2/10 Wonderful! (161 reviews) This is our third time staying at this hotel. We especially like the common area with the small kitchen. However we have noticed far less attention by the staff. There use to be plates, bowls,and cutlery. Now there is barely any of that. There is a broken French door out to the patio area that has not been fixed in over a year! The front door does not allow entry. When told about it, the staff didn't seem to care. I am afraid that the owners are allowing this place to get a bit run down and that is a shame. Reviewed on Jan 1, 2026 ![Morgan Hotel](https://images.trvl-media.com/lodging/40000000/39210000/39201700/39201680/df931c4d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Morgan Hotel CA $734 per person Apr 25 - Apr 28 found 14 hours ago Roundtrip non-stop flight included Toronto (YTO) to Vineyard Haven (MVY) 8.6/10 Excellent! (193 reviews) Room was great No staff on site Left a couple of clothes in the closet and despite calling same day and cleaning staff finding the clothes, they ended up being lost and never recovered. Will not book again. Reviewed on Dec 7, 2025 ![Harbor View Hotel](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Harbor View Hotel CA $1,087 per person Apr 25 - Apr 28 found 14 hours ago Roundtrip non-stop flight included Toronto (YTO) to Vineyard Haven (MVY) 8.8/10 Excellent! (1,000 reviews) It was pretty quiet while we were there so the breakfast was grab and go and the restaurants were closed but everything else about the hotel and the area were great. We had a lovely room - the location is perfect and there was enough going on in the town. Shame about the rain Late November Reviewed on Dec 2, 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 ![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 $137 CA $185 total Feb 15 - Feb 16 includes taxes & fees 7.8/10 Good! (1,000 reviews) I stay here alot Reviewed on Jan 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=893142&PinnedHotelID=893142&HadPinnedHotel=true®ionId=6135676) ![Iris Hotel Cape Cod ](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/63513190_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 $146 CA $168 total Mar 1 - Mar 2 includes taxes & fees 8.4/10 Very Good! (172 reviews) The bed was so comfortable. Towels thick and luxurious! Had an E station for my electric car. Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=11989&PinnedHotelID=11989&HadPinnedHotel=true®ionId=6135676) ![The Coonamessett](https://images.trvl-media.com/lodging/7000000/6600000/6591200/6591194/4add9b13_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Coonamessett 311 Gifford Street Falmouth MA Fully refundableReserve now, pay when you stay CA $180 CA $206 total Feb 27 - Feb 28 includes taxes & fees 8.6/10 Excellent! (617 reviews) The room was spacious and lovely. The room was extremely clean. The staff was friendly. The breakfast had a lovely variety including healthy options. The woman who was serving breakfast was friendly and helpful. The grounds were pretty. Our only disappointment was the noise from several trucks nearby ... Reviewed on Jan 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=27%2F02%2F2026&endDate=28%2F02%2F2026&selected=6591194&PinnedHotelID=6591194&HadPinnedHotel=true®ionId=6135676) [See all 2,171 properties in Chilmark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%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 $21 per traveller [](https://expedia.ca/things-to-do/marthas-vineyard-self-guided-driving-audio-tour.a5102813.activity-details) ![Massachusetts Highlights: Freedom Trail, Salem & More Tour](https://mediaim.expedia.com/localexpert/5247794/991bb3ab-4de4-47da-8b84-5a4e09a0b2d6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours CA $69 per adult [](https://expedia.ca/things-to-do/massachusetts-self-guided-audio-tour-bundle-10-tours.a5247794.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 $69 per traveller [](https://expedia.ca/things-to-do/massachusetts-smartphone-based-audio-tour-bundle.a5280486.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