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.
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
Price was CA $1,261, price is now CA $1,000 per person
CA $1,000
per person
Aug 26 - Aug 29
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9/10 Wonderful! (659 reviews)
Room was clean. We loved being on the 2nd floor. It was a great view of the water and the marina. Great walking distance to everything!

Reviewed on Jul 7, 2026

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was CA $1,923, price is now CA $1,483 per person
CA $1,483
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
8.8/10 Excellent! (609 reviews)
The hotel was extremely hot and humid. No AC's in the hallways around the water park and no elevators in that section of the hotel either. The overall look of the hotel was nicely done but you can tell the remodel of an old hotel focused on the aesthetics only and not the functionality of outdated HVAC systems. Since the lobby had AC and the other sections did not, the mixed temperatures created condensation to leak all over the floor and guests. The outdoor pool was on the smaller side, but my kids did enjoy it. However, we found it was not cleaned frequently which made us not want to keep returning. The hotel staff were friendly, our room AC did work and the rooms were clean. Overall, the hotel looks great in pictures but there are much better places to stay in the Cape, especially for the price.

Reviewed on Jul 6, 2026

The Richard, The Edgartown Collection

The Richard, The Edgartown Collection

3.5 out of 5
Price was CA $5,141, price is now CA $4,232 per person
CA $4,232
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Vineyard Haven (MVY)
9.6/10 Exceptional! (178 reviews)
It was conveniently located. Neat, clean and comfy.

Reviewed on Jul 4, 2026

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
Price was CA $3,346, price is now CA $2,887 per person
CA $2,887
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Vineyard Haven (MVY)
9.2/10 Wonderful! (195 reviews)
clean, updated nice decore in the room and common areas. Free Parking and a good location 10 minutes from town all were very positive. the down side : NO Staff! no one to check you in or out, no one to help with anything or make any recommendations. fully self service made it feel very low end unfortunately

Reviewed on Jul 1, 2026

Inn on Main

Inn on Main

3.5 out of 5
Price was CA $2,273, price is now CA $1,976 per person
CA $1,976
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
10/10 Exceptional! (75 reviews)
I cannot recommend this property enough. David and Ruta are amazing hosts. They are so considerate and helpful. Breakfast is wonderful and they are more than willing to accommodate any dietary needs. The property is beautiful and well maintained. They have drawers full of travel supplies, and there are fresh baked cookies every day, in your room! The Inn is very well situated and walkable to some good restaurants (plan ahead to have dinner at the Old Yarmouth Inn). The Inn on Main is really not to be missed. Thank you for the amazing weekend!

Reviewed on Jun 22, 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?

 

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Oak Bluffs Hotel Deals

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
The price is CA $677 per night from Jul 12 to Jul 13
CA $677
CA $756 total
Jul 12 - Jul 13
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Amazing hotel in the perfect location! That staff made you feel so welcomed. The best part was having beach towels/chairs available to guests and the coffee, tea, and toys for the kids at no additional cost! I can’t say how much I loved it here enough!"

Reviewed on Jul 7, 2026

Summercamp
MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue Oak Bluffs MA
The price is CA $411 per night from Jul 8 to Jul 9
CA $411
CA $495 total
Jul 8 - Jul 9
includes taxes & fees
8.8/10 Excellent! (860 reviews)
"Great experience. Friendly staff. Clean rooms and the hotel is close to literally everything. I’ll be back for sure."

Reviewed on Jul 4, 2026

MV Surfside Hotel
Pequot Hotel

Pequot Hotel

3 out of 5
19 Pequot Avenue Oak Bluffs MA
The price is CA $567 per night from Jul 8 to Jul 9
CA $567
CA $633 total
Jul 8 - Jul 9
includes taxes & fees
9.4/10 Exceptional! (601 reviews)
"The staff was very pleasant, helpful, friendly ,respectful , patience, very informative"

Reviewed on Jul 4, 2026

Pequot Hotel
See all 3,166 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.
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Stay near popular Oak Bluffs attractions

A beach with a lifeguard tower, a rocky breakwater, and the ocean.

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.
See properties

What to do in Oak Bluffs

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 Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

CA $64
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

CA $71
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 $1,000 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.