Title: Oak Bluffs Vacation Packages & Trips 2026 from CA $1,179 | Expedia.ca [Hotels in Oak Bluffs](https://expedia.ca/Oak-Bluffs-Hotels.d140231.Travel-Guide-Hotels)[Vacation Rentals in Oak Bluffs](https://expedia.ca/Oak-Bluffs-Vacation-Rentals.d140231.Travel-Guide-VacationRentals)[Flights to Oak Bluffs](https://expedia.ca/Cheap-Flights-To-Oak-Bluffs.d140231.Travel-Guide-Flights)[Oak Bluffs Car Rentals](https://expedia.ca/Car-Rentals-In-Oak-Bluffs.d140231.Car-Rental-Guide) ![](https://images.trvl-media.com/place/140231/89b7f1b0-0e2f-40ba-96da-29cde331c27b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Oak Bluffs 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 Oak Bluffs Vacation Let our vacation packages to Oak Bluffs inspire your next adventure. You'll find tons to like about this amazing city, starting with the neighborhood of Falmouth Heights, which is good for views and coastal beaches. A trip to Oak Bluffs is a wonderful opportunity to do a bit of sightseeing. Check out well-known attractions like [Inkwell Beach](https://www.expedia.ca/Inkwell-Beach-Oak-Bluffs.d6172306.Vacation-Attraction), [Oak Bluffs Town Beach](https://www.expedia.ca/Oak-Bluffs-Town-Beach-Oak-Bluffs.d6172319.Vacation-Attraction) and [Oak Bluffs Harbor](https://www.expedia.ca/Oak-Bluffs-Harbor-Oak-Bluffs.d553248621562507062.Vacation-Attraction). Expedia has what you need to escape your routine. Tailor your vacation to Oak Bluffs to suit your travel style, whatever that may be! ## Top Oak Bluffs Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Chapter House](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196169/d1cecd38_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chapter House CA $1,179 per person Jun 18 - Jun 22 found 1 day ago Roundtrip flight included Toronto (YYZ) to Hyannis (HYA) 9.2/10 Wonderful! (162 reviews) This property was clean and well maintained. There was ample parking and the staff was very friendly. Reviewed on Sep 26, 2025 ![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 19 hours 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 ![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 19 hours 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 ![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 $1,462 per person Jun 18 - Jun 22 found 1 day ago Roundtrip flight included Toronto (YYZ) to Vineyard Haven (MVY) 9/10 Wonderful! (621 reviews) We spent a night at this property and we had a great time. Thank you to the hotel staff Reviewed on Mar 18, 2026 ## Oak Bluffs Beach Vacation There's nothing like an Oak Bluffs vacation to put a bounce in your step. The soothing melody of rolling surf and the smell of fresh ocean air will help refresh your mind and body. To be close to the town centre on your trip to Oak Bluffs, find a hotel around Inkwell Beach (0.64 kilometres away). If the plan is to hang around a while, consider securing one of our Oak Bluffs vacation packages. Not only will you save some money, you'll also have other stunning beaches around you to explore, like Joseph Sylvia State Beach and Eastville Point Beach. We call that a win-win! ## Things You Should Know About Oak Bluffs - Spend your vacation by the water and let the hassles of daily life drift away with the ocean breeze. Book one of our [Oak Bluffs beach hotels](https://www.expedia.ca/d140231-tBeachHotel.Travel-Guide-Filter-Hotels?lang=en&rfrr=ATG.LP.BodyContent) and enjoy a little beachside bliss. - No matter your budget or style, you'll find an ideal place to stay for your vacation in Oak Bluffs. Why not take a look at some private vacation homes, like [The Attleboro House](https://www.expedia.ca/Oak-Bluffs-Hotels-The-Attleboro-House.h45272224.Hotel-Information) and [Marthas Vineyard Resort](https://www.expedia.ca/Oak-Bluffs-Hotels-Marthas-Vineyard-Resort.h66868932.Hotel-Information)? They're popular with visitors of all sorts. - Some 3,800 people live in Oak Bluffs. If you'd like advice about what to see and do in this area, why not start a conversation with one or two of the locals? Our [Oak Bluffs things to do page](null) is also a handy source of information. - Inkwell Beach, Oak Bluffs Harbour and Flying Horses Carousel are just some of the attractions that should be on your sightseeing list. With our Oak Bluffs vacation deals, you'll have more money in your back pocket to explore. ## Ready to book your vacation to Oak Bluffs? Choose your dates ## Oak Bluffs Hotel Deals ![Morgan Hotel](https://images.trvl-media.com/lodging/40000000/39210000/39201700/39201680/f4565200_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Morgan Hotel 9 Healy Way Oak Bluffs MA CA $216 CA $241 total Mar 25 - Mar 26 includes taxes & fees 8.4/10 Very Good! (209 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 [](https://expedia.ca/Hotel-Search?startDate=25%2F03%2F2026&endDate=26%2F03%2F2026&selected=39201680&PinnedHotelID=39201680&HadPinnedHotel=true®ionId=140231) ![The Island Inn on Martha's Vineyard](https://images.trvl-media.com/lodging/112000000/111560000/111556200/111556199/4f2a8c65_edited_2a5c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Island Inn on Martha's Vineyard 30 Island Inn Rd Oak Bluffs MA 8/10 Very Good! (32 reviews) Clean room Reviewed on Dec 27, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=111556199&PinnedHotelID=111556199&HadPinnedHotel=true®ionId=140231) [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=111556199&PinnedHotelID=111556199&HadPinnedHotel=true®ionId=140231) ![MV Surfside Hotel](https://images.trvl-media.com/lodging/3000000/2560000/2559500/2559441/7458d646_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### MV Surfside Hotel 7 Oak Bluffs Avenue Oak Bluffs MA CA $242 CA $271 total Apr 21 - Apr 22 includes taxes & fees 8.8/10 Excellent! (830 reviews) Staff members, Alex and Amoy were wonderful. They were very accommodating and friendly. Reviewed on Oct 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F04%2F2026&endDate=22%2F04%2F2026&selected=2559441&PinnedHotelID=2559441&HadPinnedHotel=true®ionId=140231) [See all 3,015 properties in Oak Bluffs](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%2F2026®ionId=140231) 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) ### Discover the most popular places to visit in Oak Bluffs ![Inkwell beach in oak bluffs on martha's vineyard](https://images.trvl-media.com/place/6172306/c1320ba4-8e7a-4a32-9247-5a588ac22d8d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Inkwell Beach If a restful vacation is part of your travel plans, Inkwell Beach might be the perfect place to seek out during your trip to Oak Bluffs. Stroll along this relaxing area's waterfront, or simply enjoy its wineries. [](https://expedia.ca/Inkwell-Beach-Oak-Bluffs.d6172306.Vacation-Attraction) #### Oak Bluffs Public Library After visiting Oak Bluffs Public Library, make a plan to see the other sights and activities in Oak Bluffs. Wander the beautiful beaches and waterfront in the area. [](https://expedia.ca/Oak-Bluffs-Public-Library-Oak-Bluffs.d6286584.Vacation-Attraction) ### What to do in Oak Bluffs ![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 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) ![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) [See all activities in Oak Bluffs](https://expedia.ca/things-to-do/search?rid=140231) ## 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