Oak Bluffs Trips (flight + hotel)

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Oak Bluffs Beach Vacation

There's nothing like an Oak Bluffs vacation to put a spring in your step. The soothing rhythm of the ocean waves and the smell of clean ocean air are sure to rejuvenate your mind and body. To be close to the town center on your trip to Oak Bluffs, base yourself around Inkwell Beach (2 kilometers away). If you're going to stay for a while, look into our Oak Bluffs vacation packages. Not only will you be able to save cash, you'll also have other beautiful beaches around you to explore, like Oak Bluffs Town Beach and Joseph Sylvia State Beach. We call that a win-win!

Top hotels in Oak Bluffs

Morgan Hotel
Morgan Hotel
2.5 out of 5
9 Healy Way, Oak Bluffs, MA
The price is P8,228 per night from 1 May to 2 May
P8,228
per night
1 May - 2 May
8.2/10 Very Good! (112 reviews)
Breathe in, breathe out - aaaaaahh!
"The hotel is finished to a high standard and makes the best of it's quaint historical building. There is no reception so access is via an app but it was not difficult to download or operate - a normal keycard will await you on your bed. It's well-located for the local eateries and the seashore and ..."

Reviewed on Apr 18, 2024

Morgan Hotel
Summercamp
Summercamp
3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
The price is P10,178 per night from 28 Apr to 29 Apr
P10,178
per night
28 Apr - 29 Apr
9/10 Wonderful! (574 reviews)
Very accommodating staff
"The front desk completely accommodated our desire to be in the main building vs the annex. They provided us with a king room with a view on the 3rd floor despite not being fully opened on the upper floors. Everyone was super hospitable & friendly. We will definitely return for another stay."

Reviewed on Apr 21, 2024

Summercamp
MV Surfside Hotel
MV Surfside Hotel
2.5 out of 5
7 Oak Bluffs Avenue, Oak Bluffs, MA
The price is P11,040 per night from 28 Apr to 29 Apr
P11,040
per night
28 Apr - 29 Apr
8.8/10 Excellent! (738 reviews)
"Accessible"

Reviewed on Nov 14, 2023

MV Surfside Hotel
See all 3,063 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 vacation package cost?
Maybe less than you imagined — from a low , in fact! By combining hotels, flights and car rentals into your own custom-made vacation package, your getaway to Oak Bluffs is just clicks away.
How do I get a cheap travel package to Oak Bluffs?
Bundle your flights and hotels with Expedia to save big bucks on your next adventure. With more than 550 airlines and 1,000,000 hotel options throughout the world, your Oak Bluffs vacation package can be customized exactly to suit your travel style. With all that extra cash, why not include some interesting experiences and tours? It’s an easy way to unlock even more bargains. Your dream vacation in Oak Bluffs is closer than you thought!
Where should I stay in Oak Bluffs?
With lots to explore in Oak Bluffs, it’d be handy for you to book a room in a hotel close to its attractions. Inkwell Beach, Oak Bluffs Town Beach and Oak Bluffs Harbor are some popular ones to add to your itinerary.
What are the top hotels in Oak Bluffs?
Summercamp and MV Surfside Hotel are some excellent options in the neighborhood of Lagoon Heights. If you’d like to stay in the East Chop area, consider locking in a room at Pequot Hotel or Morgan Hotel.
How far in advance should I book my Oak Bluffs vacation?
It all depends on the airline, but you can generally browse through international airfares on Expedia up to a year in advance. While it’s a good idea to book ahead of time, lucky travelers will sometimes find a cheaper ticket just weeks before their intended journey.
What does an Expedia Oak Bluffs travel package include?
Hotels, car rentals and flights — we bring you all the best deals. All you have to do is decide on your preferred combination. Once you’ve made your booking, you can add on the exciting stuff like tours and experiences. Our travel packages make it simple to craft an awesome Oak Bluffs vacation.
What should I know before booking an Oak Bluffs travel package?
You’ll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and unlock terrific discounts. Hotels aren’t your only option, though. We have beachside condos, city apartments and even treehouses and ranches!
Can I choose my airline with an Oak Bluffs Expedia vacation package?
Most definitely. Expedia has access to more than 550 airlines worldwide, so you can customize your Oak Bluffs trip according to your budget and travel needs.
If I'm not able to travel, can I cancel my Oak Bluffs vacation package?
Yes, you can cancel your Oak Bluffs booking if your travel plans have changed. Whether you’ll incur a fee or not depends on your hotel, airline or car rental company. You may be able to cancel or change your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

Popular places to visit

Image for East Chop Light

East Chop Light

You can find out about the history of East Chop with a visit to East Chop Light. Stroll along the area's waterfront, or simply savor its wineries.

East Chop Light
Image for Inkwell Beach

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
Image for Oak Bluffs Ferry Terminal

Oak Bluffs Ferry Terminal

Explore the waterfront in Oak Bluffs with a trip to Oak Bluffs Ferry Terminal. Stroll along this relaxing area's beaches, or simply enjoy its wineries.

Oak Bluffs Ferry Terminal

What to do in Oak Bluffs

Image for Marthas Vineyard Tour: Self-Guided Drive

Marthas Vineyard Tour: Self-Guided Drive

P746
Per adult
86% of travellers recommend
Marthas Vineyard Tour: Self-Guided Drive
Image for Martha's Vinyard Driving & Walking GPS-Guided Audio Tour

Martha's Vinyard Driving & Walking GPS-Guided Audio Tour

P829
Per adult
Martha's Vinyard Driving & Walking GPS-Guided Audio Tour
Image for Oak Bluffs, Martha's Vineyard Audio Tour

Oak Bluffs, Martha's Vineyard Audio Tour

P692
Per adult
Oak Bluffs, Martha's Vineyard Audio Tour
See all activities in Oak Bluffs

More trip options

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