Oak Bluffs Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Oak Bluffs

Summercamp
Summercamp
3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
The price is 12.838.740 ₫ per night from 9 Jul to 10 Jul
12.838.740 ₫
14.340.872 ₫ total
9 Jul - 10 Jul
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Awesome location. Great staff!!"

Reviewed on 27 Jun 2025

Summercamp
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 10.786.321 ₫ per night from 2 Jul to 3 Jul
10.786.321 ₫
17.577.029 ₫ total
2 Jul - 3 Jul
includes taxes & fees
8/10 Very Good! (3 reviews)
"The staff is absolutely wonderful. Beautiful Property. Well worth the money!"

Reviewed on 3 Jun 2025

The Island Inn on Martha's Vineyard
Pequot Hotel
Pequot Hotel
3 out of 5
19 Pequot Avenue, Oak Bluffs, MA
The price is 9.629.055 ₫ per night from 2 Jul to 3 Jul
9.629.055 ₫
10.755.576 ₫ total
2 Jul - 3 Jul
includes taxes & fees
9.2/10 Wonderful! (517 reviews)
"The Pequot was a perfect place to stay in Oak Bluffs, close to the beach and shopping, restaurants, tourist spots. Yet, it was tucked away on a quiet street full of cute gingerbread style homes. The hotel had a good size front porch to relax on and a charming lobby. The free breakfast had a nice ..."

Reviewed on 27 Jun 2025

Pequot Hotel
See all 3,163 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.

Popular places to visit

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

Oak Bluffs Town Beach

4/5(1 review)

If a restful holiday is part of your travel plans, Oak Bluffs Town Beach might be the perfect place to visit during your trip to Oak Bluffs. Stroll along the waterfront or visit the shops in this relaxing area.

Oak Bluffs Town Beach

Oak Bluffs Harbor

4.5/5(17 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.

Oak Bluffs Harbor