Oak Bluffs Vacations from $484

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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!

The Latest Oak Bluffs vacation packages

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Save 100% on your flight
Price was $709, price is now $484 per person
$484
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Hyannis (HYA)
8.8/10 Excellent! (278 reviews)
Very family friendly, great pool, multiple fire pit for roasting marshmallows, indoor heated water park, arcade games. There is a cafe, a gift shop, a bar and restaurant with a door and out in the center of the resort where there is fire piths, a ballroom inside for free dance lessons. There is free live music multiple times per day, and much more activities to keep families with young kids entertained. There is a text through out the day alerting for the activities. If you don’t have a car and want to go anywhere, the resort offers shuttle services to drop you off anywhere in town and pick you up.

Reviewed on Aug 23, 2025

Chapter House

Chapter House

3.5 out of 5
Save 100% on your flight
Price was $1,296, price is now $864 per person
$864
per person
Oct 12 - Oct 17
found 16 hours ago
Roundtrip flight included
New York (NYC) 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

Inn on Main

Inn on Main

3.5 out of 5
Save 100% on your flight
Price was $849, price is now $647 per person
$647
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Hyannis (HYA)
10/10 Exceptional! (70 reviews)
What a great place! Central location made it super easy to get around. Hosts were fantastic- very nice, welcoming and very helpful with great restaurant, beach or visit recommendations. I highly recommend The Inn on Main.

Reviewed on Aug 7, 2025

The Coco, The Edgartown Collection

The Coco, The Edgartown Collection

3 out of 5
Price was $1,706, price is now $1,343 per person
$1,343
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9.6/10 Exceptional! (56 reviews)
Staff was very accomodating..Breakfast was excellent..room was beautiful. Close to lots of restaurants and shops..i loved it all.

Reviewed on Jul 21, 2025

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $629, price is now $509 per person
$509
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Hyannis (HYA)
9.4/10 Exceptional! (1,003 reviews)
The hotel is very well managed nicely maintained. Great harbour location for catching the ferries as well. The breakfast is prepackaged items designed for grab and go.

Reviewed on Aug 19, 2025

Don't see what you're looking for?
See all available trips from Columbus to Oak Bluffs
View all trips

Discover the most popular places to visit in Oak Bluffs

Sandy beaches, farmlands, fishing docks, harbor towns and tall lighthouses, Its Martha's Vineyard! It is around an hour of boat ride from Cape Cod to the Oak Bluffs. MV accessible only by boat or air. This picture was of course taken in summer :) Bright sunny day with blue sky and lush green. In the background is the famous east chop lighthouse. The best of my memories of MV are from East Chop. We rented a bright Red scooter near the Oak Bluffs harbor after getting off from ferry, kicked off our slippers, rode to the sunset ;) I meant we drove to East Chop:) Must Do : Get that pretty but awfully slow red scooter, drive to the light house, live the dream :)

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 beautiful beaches, or simply savor its seafood restaurants.

East Chop Light

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 Town Beach

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

Oak Bluffs Town Beach

What to do in Oak Bluffs

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

$50
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
4 hours Hop-on Hop-off Jawsome Jaws Tour

4 hours Hop-on Hop-off Jawsome Jaws Tour

$120
per adult
4 hours Hop-on Hop-off Jawsome Jaws Tour
See all activities in Oak Bluffs

Oak Bluffs Hotel Deals

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
$311 nightly
The price is $347 total per night from Sep 21 to Sep 22
$347 total
Sep 21 - Sep 22
Total with taxes and fees
9.2/10 Wonderful! (1,007 reviews)
"My husband and I celebrated our 46th wedding anniversary. The hotel surprised us with silk rose petals, champagne, and balloons. We really appreciated it. The only complaint is the people above our room(203) were very noisy into the wee hours of the night and early morning."

Reviewed on Aug 22, 2025

Summercamp
MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue, Oak Bluffs, MA
$354 nightly
The price is $394 total per night from Sep 1 to Sep 2
$394 total
Sep 1 - Sep 2
Total with taxes and fees
8.8/10 Excellent! (814 reviews)
"I didnt like that there was no elevator. I am in my 60's. I was on the 3rd floor, no elevator. Loved everything else...I will return. Hopefully to an elevator."

Reviewed on Aug 23, 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
$353 nightly
The price is $394 total per night from Sep 3 to Sep 4
$394 total
Sep 3 - Sep 4
Total with taxes and fees
7.8/10 Good! (17 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.

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 center on your trip to Oak Bluffs, find a hotel around Inkwell Beach (0.4 miles 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 Harbor 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Oak Bluffs vacation package cost?
You can snap up a vacation package to this destination from $484 on Expedia. But how much your vacation 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?
October, November and December are the best times to look for cheap Oak Bluffs vacation packages. Opting to travel in quieter months means you can typically find reduced prices on accommodations and flights.
How many days is enough for Oak Bluffs?
Dedicate around 3 days for your Oak Bluffs vacation if you're hoping to discover all that makes this destination unique. Stroll around popular neighborhoods, including Lagoon Heights and East Chop. Then head to the major sights such as Joseph Sylvia State Beach and Eastville Point Beach. With a well-planned itinerary, you can keep busy with room for some rest time too. Want to venture outside of Oak Bluffs? Consider squeezing in a day trip or two.
Is it worth booking a vacation package to Oak Bluffs?
Oak Bluffs is a good vacation destination with attractions like Inkwell Beach among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, an Oak Bluffs vacation promises a good time for everyone.
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 vacation as a package?
You can enjoy significant savings on your Oak Bluffs getaway by booking a personalized vacation 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 vacation 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. Choose when to go: Check your calendar and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to visit Oak Bluffs.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and food to activities and flights. Your hotel will probably be the biggest expense during your trip to Oak Bluffs.
  3. Use our trip planning tool to explore Oak Bluffs: Research every part of your trip to Oak Bluffs with this handy planner. Invite your friends and family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you know more about Oak Bluffs, you can figure out the right length of your break. Create a rough itinerary and allocate enough time to get through everything on your must-do list.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalized Oak Bluffs vacation package.
  6. Book any day trips or activities: Here's the fun part — locking in everything you want to see and do. Explore some of the top things to do in Oak Bluffs and book your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Oak Bluffs vacation packages?
Secure your dream getaway to Oak Bluffs with Expedia's Book Now, Pay Later vacations. No need to save like crazy or hold off until your next payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you spread the total cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stay on budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.