Oak Bluffs Vacation Packages
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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, Oak Bluffs Town Beach and Oak Bluffs Harbor. 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.
Faraway Martha's Vineyard
CA $1,476
per person
Sep 28 - Oct 1
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
Common spaces like the lobby and the pool were excellent, but those are the only good things to say about this property. Our room (104) was dark and had no privacy. There are no chests of drawers to put away clothes (they put bar glasses in them), the fixtures in the bathroom are loose and rusty and covered with water spots. There were stains on the carpet, which felt dirty, and a crack in the bathroom ceiling. The safe was too small for a standard laptop so good luck with that. There was no real hospitality to speak of as most of the time the people at the front desk do not even look up from their phones or desks to greet you when you walk by. We felt like this was a massive waste of money. On top of it all, they charged me $197 after I had left and when I called to ask what for they never answer or return messages. Never again.
Reviewed on Aug 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 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 and Marthas Vineyard Resort? 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 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?
Oak Bluffs Hotel Deals
Summercamp
70 Lake Avenue Oak Bluffs MA
CA $454
CA $507 total
Sep 13 - Sep 14
includes taxes & fees
MV Surfside Hotel
7 Oak Bluffs Avenue Oak Bluffs MA
CA $370
CA $448 total
Sep 1 - Sep 2
includes taxes & fees
Morgan Hotel
9 Healy Way Oak Bluffs MA
CA $432
CA $483 total
Sep 8 - Sep 9
includes taxes & fees
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.
Stay near popular Oak Bluffs attractions
Inkwell Beach
9.0/10 (154 reviews)
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.
Oak Bluffs Harbor
9.2/10 (510 reviews)
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.
Photo by Fun Travelog
Oak Bluffs Town Beach
9.4/10 (134 reviews)
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.
Ocean Park
9.2/10 (99 reviews)
Ocean Park is just one of the places to see in Oak Bluffs, so why not enjoy the other things to explore during your travels? Wander the area's waterfront or simply enjoy one of its seafood restaurants.
Flying Horses Carousel
8.6/10 (106 reviews)
Enjoy an outing to Flying Horses Carousel during your stay in Oak Bluffs. Wander the beautiful beaches and waterfront in the area.
Circuit Avenue
9.2/10 (82 reviews)
During your trip to Oak Bluffs, you can search for that perfect souvenir at Circuit Avenue. Wander the beaches and waterfront in this relaxing area.
Oak Bluffs Fishing Pier
After visiting Oak Bluffs Fishing Pier, make a plan to see the other sights and activities in Oak Bluffs. Stroll along the beaches or visit the shops in this relaxing area.
Farm Neck Golf Club
8.2/10 (16 reviews)
Enjoy a round of golf in Oak Bluffs at Farm Neck Golf Club. Wander the area's waterfront or simply enjoy one of its wineries.
What to do in Oak Bluffs
Martha's Vineyard: Self-Guided Driving Audio Tour
CA $21
per traveller
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
CA $70
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
CA $71
per traveller
Frequently asked questions
How much does an Oak Bluffs vacation package cost?
You'll find cheap prices from CA $1,259 on Expedia for your Oak Bluffs getaway. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Oak Bluffs costs.
What are the cheapest months to go to Oak Bluffs?
January, February and November are great times to search for cheap Oak Bluffs vacation packages. Opting to travel in less busy periods means you can generally find lower prices on flights and accommodations.
How many days is enough for Oak Bluffs?
To get the most out of an Oak Bluffs vacation, we recommend staying for 3 days. Split your time between discovering Martha's Vineyard Preservation Trust Historic Buildings, Lighthouse Beach and other well-known attractions, on top of experiencing neighbourhoods like Lagoon Heights and East Chop. If you've got some time to spare, add a tour or day trip to your Oak Bluffs vacation itinerary.
Is it worth booking a vacation package to Oak Bluffs?
It's no wonder an Oak Bluffs vacation is on the must-do list of many travellers. Popular attractions like Inkwell Beach are just the start of things to see and do here.
How to find the best Oak Bluffs package deals?
Use Expedia's handy filters to find some of the best Oak Bluffs package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Oak Bluffs package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book an Oak Bluffs vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still get the freedom to create a tailored Oak Bluffs vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Oak Bluffs?
If you've got your Oak Bluffs vacation dates confirmed, book as early as you can to grab some unbeatable deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Oak Bluffs?
- Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Oak Bluffs.
- Plan your budget wisely: In addition to the cost of your accommodations, you should consider other expenses. These include food, transportation and flights. Also, put aside a little extra for unexpected expenses that could arise during your trip to Oak Bluffs.
- Set the duration of your trip: Start by listing all the attractions and activities you want to experience in Oak Bluffs. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalized Oak Bluffs vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
