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.
Morgan Hotel

Morgan Hotel

2.5 out of 5
Price was CA $1,226, price is now CA $915 per person
CA $915
per person
Oct 17 - Oct 22
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Vineyard Haven (MVY)
8.4/10 Very Good! (167 reviews)
great location, small but modern

Reviewed on Aug. 19, 2025

The Christopher, The Edgartown Collection

The Christopher, The Edgartown Collection

3 out of 5
Price was CA $2,028, price is now CA $1,387 per person
CA $1,387
per person
Oct 17 - Oct 22
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Vineyard Haven (MVY)
9.8/10 Exceptional! (222 reviews)
Great location, fantastic room, friendly staff and local dining options

Reviewed on Aug. 20, 2025

Chapter House

Chapter House

3.5 out of 5
Price was CA $1,476, price is now CA $1,022 per person
CA $1,022
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
9.2/10 Wonderful! (156 reviews)
Really enjoyed the bar, which was a great spot for a late afternoon drink before dinner

Reviewed on Aug. 2, 2025

Faraway Martha's Vineyard

Faraway Martha's Vineyard

3.5 out of 5
Price was CA $1,877, price is now CA $1,358 per person
CA $1,358
per person
Oct 17 - Oct 22
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Vineyard Haven (MVY)
9/10 Wonderful! (1,001 reviews)
Beautifully decorated and nice workspace. Staff was not helpful with baggage at check-in. For the price, the toilet paper was cheap and no slippers. It was very nice that they allowed you to use the pool and property after the 11am checkout.

Reviewed on Aug. 9, 2025

The Sydney, The Edgartown Collection

The Sydney, The Edgartown Collection

3.5 out of 5
Price was CA $2,253, price is now CA $1,683 per person
CA $1,683
per person
Oct 17 - Oct 22
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Vineyard Haven (MVY)
9.4/10 Exceptional! (163 reviews)
Fresh breakfast from local farm was excellent. Close to many shops and restaurants. Would stay here again.

Reviewed on Jul. 13, 2025

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?

 

Choose your dates

Oak Bluffs Hotel Deals

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
The price is CA $442 per night from Sep 21 to Sep 22
CA $442
CA $494 total
Sep 21 - Sep 22
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Staff was knowledgeable and personal. Hotel was convenient and met all of my needs."

Reviewed on Aug. 20, 2025

Summercamp
MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue, Oak Bluffs, MA
The price is CA $478 per night from Sep 1 to Sep 2
CA $478
CA $548 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (812 reviews)
"Amid the most busy nexus in MV, Surfside is a great place to stay. First time there, and we enjoyed it."

Reviewed on Aug. 18, 2025

MV Surfside Hotel
The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
30 Island Inn Rd, Oak Bluffs, MA
The price is CA $238 per night from Sep 3 to Sep 4
CA $238
CA $526 total
Sep 3 - Sep 4
includes taxes & fees
7.8/10 Good! (15 reviews)
"Great spot, very clean and convenient."

Reviewed on Aug. 13, 2025

The Island Inn on Martha's Vineyard
See all 3,134 properties in Oak Bluffs
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Discover the most popular places to visit in Oak Bluffs

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.

Inkwell Beach

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.

Oak Bluffs Public Library

What to do in Oak Bluffs

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

CA $69
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Martha's Vineyard Self-Driving Audio Tour

Martha's Vineyard: Self-Guided Driving Audio Tour

CA $21
per traveller
Martha's Vineyard: Self-Guided Driving Audio Tour
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

CA $69
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Oak Bluffs

Frequently asked questions

How much does an Oak Bluffs vacation package cost?
You'll find cheap prices from CA $915 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.