Oak Bluffs Holidays

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Oak Bluffs Holiday

Oak Bluffs Beach Holiday

There's nothing like an Oak Bluffs holiday 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 holiday 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 holiday 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 holiday in Oak Bluffs. Why not take a look at some private holiday 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 holiday deals, you'll have more money in your back pocket to explore.

Our pick of the best Oak Bluffs Hotel Deals

Summercamp
Summercamp
3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
The price is NZ$787 per night from 30 June to 1 July
NZ$787
30 June - 1 July
includes taxes & fees
9.2/10 Wonderful! (998 reviews)
"I gave an overall rating of 4 because my room was so small, I was totally miserable. This Queen ocean view room, in the older part of the hotel is not worth the rate of over $550 per night. I regret not reserving a king room. I definitely will not make that mistake again. The property itself is an ..."

Reviewed on 22 Jun. 2025

Summercamp
Pequot Hotel
Pequot Hotel
3 out of 5
19 Pequot Avenue, Oak Bluffs, MA
The price is NZ$558 per night from 26 June to 27 June
NZ$558
26 June - 27 June
includes taxes & fees
9.2/10 Wonderful! (515 reviews)
"This is an amazing property. It is my second stay there… The staff are just lovely. The room was very quiet and had everything we needed. They do provide beach towels and beach chairs complementary should you need them. They do not have a place to store your luggage. Should you arrive early or depart ..."

Reviewed on 17 Jun. 2025

Pequot Hotel
The Island Inn on Martha's Vineyard
The Island Inn on Martha's Vineyard
2 out of 5
30 Island Inn Rd, Oak Bluffs, MA
The price is NZ$744 per night from 29 June to 30 June
NZ$744
29 June - 30 June
includes taxes & fees
10/10 Exceptional! (2 reviews)
"The staff is absolutely wonderful. Beautiful Property. Well worth the money!"

Reviewed on 3 Jun. 2025

The Island Inn on Martha's Vineyard
See all 3,147 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.

Frequently asked questions

How much does an Oak Bluffs holiday package cost?
You can snap up a holiday package to this destination on Expedia. But how much your holiday to Oak Bluffs costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Oak Bluffs?
You can usually find reduced prices and greater availability in January, February and November. Take a look at our cheap Oak Bluffs holiday packages and you could score some great off-season discounts.
How many days is enough for Oak Bluffs?
Dedicate around 3 days for your Oak Bluffs holiday if you want to discover everything that makes this place special. Explore popular neighbourhoods, including Lagoon Heights and East Chop. Then tick off major sights like Eastville Point Beach and Eastville Beach. With a good itinerary, you can keep busy with room for some me-time too. Want to venture outside of Oak Bluffs? Consider an excursion or two.
Is it worth booking a holiday package to Oak Bluffs?
Oak Bluffs offers everything you need for an amazing escape. Begin your Oak Bluffs holiday on a high note by exploring popular attractions like Inkwell Beach.
How to find the best Oak Bluffs package deals?
Start your search for an Oak Bluffs package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Oak Bluffs package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oak Bluffs adventure underway.
Is it cheaper to book an Oak Bluffs holiday as a package?
You can enjoy significant savings on your Oak Bluffs getaway by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Oak Bluffs?
Land incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Oak Bluffs trip.
How to plan a trip to Oak Bluffs?

  1. Pick your travel dates: The things you want to do in Oak Bluffs and your preferred season will help you decide when to travel.
  2. Set your budget: Consider costs like flights, meals and transportation when working out how much to save for your trip to Oak Bluffs. Then, choose a property that fits your budget, whether that's a wallet-friendly stay or a deluxe retreat.
  3. Decide how long to go away for: Now that you're more familiar with Oak Bluffs, you can figure out the perfect length of your holiday. Pull together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalised Oak Bluffs holiday package.

Discover the most popular places to visit in Oak Bluffs

Inkwell Beach

If a restful holiday is part of your travel plans, Inkwell Beach might be the perfect place to visit during your trip to Oak Bluffs. Stroll along this relaxing area's waterfront or simply enjoy its wineries.

Inkwell Beach

What to do in Oak Bluffs

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

NZ$83
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Martha's Vineyard Self-Driving Audio Tour

Martha's Vineyard: Self-Guided Driving Audio Tour

NZ$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

NZ$70
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Oak Bluffs
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.