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.
Inn on Main
CA $999
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Hyannis (HYA)
10/10 Exceptional! (79 reviews)
Very accommodating hosts , Dave & Ruta. Delicious 2 course breakfast.Room was clean, very comfortable and great amenities. Hosts were very helpful regarding dining and touring ideas. Highly recommend
Reviewed on Aug 8, 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 $261
CA $291 total
Oct 7 - Oct 8
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Staying at Summercamp was an enjoyable experience. The staff was super friendly and informative. The room was clean and well maintained. Overall just a terrific property and we enjoyed our stay!"
Reviewed on Sep 10, 2026
MV Surfside Hotel
7 Oak Bluffs Avenue Oak Bluffs MA
8.8/10 Excellent! (909 reviews)
"Price was cheap for that time of year. Room smelled a little musty opened windows and let air out for couple hours wasn’t bad room was clean close to beach and shopping and dining."
Reviewed on Sep 7, 2026
Pequot Hotel
19 Pequot Avenue Oak Bluffs MA
CA $275
CA $307 total
Oct 4 - Oct 5
includes taxes & fees
9.4/10 Exceptional! (616 reviews)
"Staff was very helpful. Gave us the option to stay on the main floor bc we had a bunch of bags and a baby. Cute little breakfast area. Homey feel."
Reviewed on Sep 5, 2026
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 wineries.
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.
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 seafood restaurants.
Oak Bluffs Public Library
7.8/10 (27 reviews)
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.
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 $69
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
CA $69
per traveller
Frequently asked questions
How much does an Oak Bluffs vacation package cost?
You'll find cheap prices from CA $500 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.
