Title: Oak Bluffs Vacation Packages 2026 from $559 | Expedia.com [Oak Bluffs Travel Guide](https://expedia.com/Oak-Bluffs.dx140231)[Hotels in Oak Bluffs](https://expedia.com/Oak-Bluffs-Hotels.d140231.Travel-Guide-Hotels)[Vacation Rentals in Oak Bluffs](https://expedia.com/Oak-Bluffs-Vacation-Rentals.d140231.Travel-Guide-VacationRentals)[Flights to Oak Bluffs](https://expedia.com/Cheap-Flights-To-Oak-Bluffs.d140231.Travel-Guide-Flights)[Things to do in Oak Bluffs](https://expedia.com/Things-To-Do-In-Oak-Bluffs.d140231.Travel-Guide-Activities)[Car Rentals in Oak Bluffs](https://expedia.com/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 Vacations from $559 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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.com/Inkwell-Beach-Oak-Bluffs.d6172306.Vacation-Attraction), [Oak Bluffs Town Beach](https://www.expedia.com/Oak-Bluffs-Town-Beach-Oak-Bluffs.d6172319.Vacation-Attraction) and [Oak Bluffs Harbor](https://www.expedia.com/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! ## The Latest Oak Bluffs vacation packages Price found within the past 48 hours. Click for updated prices. ![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 $559 per person Apr 23 - Apr 27 found 3 hours ago Roundtrip flight included New York (NYC) to Vineyard Haven (MVY) 9/10 Wonderful! (605 reviews) Friendly staff, nice clean room Reviewed on Feb 6, 2026 ![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Margaritaville Resort Cape Cod Save 100% on your flight $951 per person May 21 - May 25 found 1 day ago Roundtrip flight included Charlotte (CLT) to Hyannis (HYA) 8.8/10 Excellent! (401 reviews) The updates they made are beautiful. You really feel like you’re in the Caribbean if you don’t step outside. All the staff I encountered were super helpful and courteous. The water park was closed for unforeseen maintenance for a day and a half which happened to be out last days so that was disappointing to our 8 year old. The food I would say was just OK for the price. The margaritas made up for the food - yum! We will def go back. Reviewed on Feb 25, 2026 ![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 $730 per person May 21 - May 25 found 1 day ago Roundtrip flight included Charlotte (CLT) 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 ![Anchor In Distinctive Waterfront Lodging](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640889/7438dff7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Anchor In Distinctive Waterfront Lodging $927 per person May 21 - May 25 found 1 day ago Roundtrip flight included Charlotte (CLT) to Hyannis (HYA) 9.4/10 Exceptional! (1,000 reviews) The staff were all very nice. The rooms were nice, spacious, and very, very clean. 5 stars Reviewed on Feb 18, 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 $1,390 per person May 21 - May 25 found 1 day ago Roundtrip non-stop flight included Charlotte (CLT) to Vineyard Haven (MVY) 8.6/10 Excellent! (193 reviews) This is a quiet, comfortable, clean environment in walking distance to stores, the beach, restaurants, the post office, and the bus stop. There is parking in front of and a short distance walk from the hotel. The rooms are updated and offer what is needed for a relaxing stay. Reviewed on Feb 13, 2026 Don't see what you're looking for? See all available trips from Columbus to Oak Bluffs [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-26/2026-04-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ACK&NumRoom=1&NumAdult=2&NumChild=0&paandie=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=PKG_SPRING_PROMO_140231) ### 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.com/Inkwell-Beach-Oak-Bluffs.d6172306.Vacation-Attraction) ![Oak Bluffs Harbor](https://images.trvl-media.com/place/553248621562507062/31157d33-1d5f-4d71-8f09-f88628a128e8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Oak Bluffs Harbor Explore the waterfront in Oak Bluffs with a trip to Oak Bluffs Harbor. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants. [](https://expedia.com/Oak-Bluffs-Harbor-Oak-Bluffs.d553248621562507062.Vacation-Attraction) ![After five+ months of cold weather, occasional snowstorms and chilly rains, New England acquires an enviable summer spirit. The turquoise, blue waves, though mildly cool in the month of June, shimmer under the watchful eye of the powerful sun. Alternating between dips in the water and lazy siestas on the sand, we thanked our lucky stars for deciding to book a stay at Martha’s Vineyard months in advance, which just happened to coincide with a spectacularly breezy and warm weekend. Have you been blessed with good weather during your travels? #BVSBlue ](https://images.trvl-media.com/place/140231/c2afe9cb-8907-432a-98f7-038323ba90e5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Oak Bluffs Town Beach If a restful vacation is part of your travel plans, Oak Bluffs Town Beach might be the perfect place to seek out during your trip to Oak Bluffs. Stroll along the waterfront or visit the shops in this relaxing area. [](https://expedia.com/Oak-Bluffs-Town-Beach-Oak-Bluffs.d6172319.Vacation-Attraction) ### What to do in Oak Bluffs ![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 $50 per adult [](https://expedia.com/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 $50 per traveler [](https://expedia.com/things-to-do/massachusetts-smartphone-based-audio-tour-bundle.a5280486.activity-details) [See all activities in Oak Bluffs](https://expedia.com/things-to-do/search?rid=140231) ## Oak Bluffs Hotel Deals ![Summercamp](https://images.trvl-media.com/lodging/11000000/10060000/10058600/10058501/4ff1c19a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Summercamp 70 Lake Avenue Oak Bluffs MA 9.2/10 Wonderful! (1,000 reviews) Lovely stay and the staff was friendly and helpful. Excellent location. Reviewed on Dec 17, 2025 [Get rates](https://expedia.com/Hotel-Search?startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&selected=10058501&PinnedHotelID=10058501&HadPinnedHotel=true®ionId=140231) [](https://expedia.com/Hotel-Search?startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&selected=10058501&PinnedHotelID=10058501&HadPinnedHotel=true®ionId=140231) ![Morgan Hotel](https://images.trvl-media.com/lodging/40000000/39210000/39201700/39201680/df931c4d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Morgan Hotel 9 Healy Way Oak Bluffs MA $148 nightly $165 total Mar 16 - Mar 17 Total with taxes and fees 8.4/10 Very Good! (206 reviews) This is a quiet, comfortable, clean environment in walking distance to stores, the beach, restaurants, the post office, and the bus stop. There is parking in front of and a short distance walk from the hotel. The rooms are updated and offer what is needed for a relaxing stay. Reviewed on Feb 13, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%2F2026&selected=39201680&PinnedHotelID=39201680&HadPinnedHotel=true®ionId=140231) ![MV Surfside Hotel](https://images.trvl-media.com/lodging/3000000/2560000/2559500/2559441/79b0f80c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### MV Surfside Hotel 7 Oak Bluffs Avenue Oak Bluffs MA 8.8/10 Excellent! (830 reviews) Staff members, Alex and Amoy were wonderful. They were very accommodating and friendly. Reviewed on Oct 14, 2025 [Get rates](https://expedia.com/Hotel-Search?startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&selected=2559441&PinnedHotelID=2559441&HadPinnedHotel=true®ionId=140231) [](https://expedia.com/Hotel-Search?startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&selected=2559441&PinnedHotelID=2559441&HadPinnedHotel=true®ionId=140231) [See all 2,972 properties in Oak Bluffs](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F27%2F2026&endDate=2%2F28%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. ## Find the Best Oak Bluffs Vacation Packages ## 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 center on your trip to Oak Bluffs, find a hotel around Inkwell Beach (0.4 miles 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.com/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.com/Oak-Bluffs-Hotels-The-Attleboro-House.h45272224.Hotel-Information) and [Marthas Vineyard Resort](https://www.expedia.com/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 Harbor 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. ## Oak Bluffs Essential Information | Language | English | | --------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Martha's Vineyard Airport (MVY) | | Population | 3,800 | | Max Temp Winter | 40ºF | | Max Temp Summer | 70ºF | | Top Sights | [Inkwell Beach](https://www.expedia.com/Inkwell-Beach-Oak-Bluffs.d6172306.Vacation-Attraction), [Old Silver Beach](https://www.expedia.com/Old-Silver-Beach-Massachusetts.d6070199.Vacation-Attraction) and [Falmouth Heights Beach](https://www.expedia.com/Falmouth-Heights-Beach-Falmouth-Heights.d553248631819778244.Vacation-Attraction) | ## More vacations you might like ![](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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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[](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does an Oak Bluffs vacation package cost? ### What are the cheapest months to go to Oak Bluffs? ### How many days is enough for Oak Bluffs? ### Is it worth booking a vacation package to Oak Bluffs? ### How to find the best Oak Bluffs package deals? ### Is it cheaper to book an Oak Bluffs vacation as a package? ### When to book a vacation package to Oak Bluffs? ### How to plan a trip to Oak Bluffs? > 1. Choose when to go: Check your calendar and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to visit Oak Bluffs. > 2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and food to activities and flights. Your hotel will probably be the biggest expense during your trip to Oak Bluffs. > 3. Use our [trip planning tool](https://www.expedia.com/why/trip-planning) to explore Oak Bluffs: Research every part of your trip to Oak Bluffs with this handy planner. Invite your friends and family to collaborate on a group trip, search for stays or things to do and make bookings. > 4. Decide how long to go for: Now that you know more about Oak Bluffs, you can figure out the right length of your break. Create a rough itinerary and allocate enough time to get through everything on your must-do list. > 5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalized Oak Bluffs vacation package. > 6. Book any day trips or activities: Here's the fun part — locking in everything you want to see and do. Explore some of the top [things to do in Oak Bluffs](https://www.expedia.com/Things-To-Do-In-Oak-Bluffs.d140231.Travel-Guide-Activities) and book your tickets in advance to save time (and maybe some dollars too!). ### Does Expedia offer Book Now, Pay Later Oak Bluffs vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Hotels near Trinity Park Tabernacle ](https://www.expedia.com/Trinity-Park-Tabernacle-Hotels.0-l6172300-0.Travel-Guide-Filter-Hotels) - [Hotels near Cottage Museum ](https://www.expedia.com/Cottage-Museum-Hotels.0-l6287127-0.Travel-Guide-Filter-Hotels) - [Hotels near Circuit Avenue ](https://www.expedia.com/Circuit-Avenue-Hotels.0-l6287415-0.Travel-Guide-Filter-Hotels) - [Hotels near Oak Bluffs Public Library ](https://www.expedia.com/Oak-Bluffs-Public-Library-Hotels.0-l6286584-0.Travel-Guide-Filter-Hotels) - [Hotels near Ocean Park ](https://www.expedia.com/Ocean-Park-Hotels.0-l6172297-0.Travel-Guide-Filter-Hotels) - 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