Oak Bluffs Vacations from $791

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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!

The Latest Oak Bluffs vacation packages

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 $1,251, price is now $791 per person
$791
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9/10 Wonderful! (659 reviews)
Was a decent hotel. Nothing incredible but pretty clean for what it is. Staff was great. Beach was closed due bacteria from rain. Area near hotel needs improvements.

Reviewed on Jul 12, 2026

Morgan Hotel

Morgan Hotel

2.5 out of 5
Price was $1,616, price is now $1,140 per person
$1,140
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.6/10 Excellent! (233 reviews)
Excellent location and superb staff. Very helpful .

Reviewed on Jul 10, 2026

Faraway Martha's Vineyard

Faraway Martha's Vineyard

4 out of 5
Price was $3,242, price is now $2,501 per person
$2,501
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
Great location. Very quaint hotel. Loved the pool and bar.

Reviewed on Jul 9, 2026

Harbor View Hotel

Harbor View Hotel

5 out of 5
Price was $2,446, price is now $1,901 per person
$1,901
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
Property was Beautiful. Only downside was there is no Elevator in the area we stayed which was a pain being on 3rd floor with a baby/carrage etc. My fault for not checking ahead of time but other than that the place was great. Close walking distance to downtown Edgartown. Staff was very friendly and accomodating.

Reviewed on Jun 24, 2026

The Coco, The Edgartown Collection

The Coco, The Edgartown Collection

3 out of 5
Price was $2,010, price is now $1,598 per person
$1,598
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9.6/10 Exceptional! (74 reviews)

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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)
Inkwell Beach: a historic summer haven for African American families since the late 1800s. Join the morning "Polar Bears" swim group or practice beachside yoga while enjoying the calm waters and cultural significance.
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What to do in Oak Bluffs

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

$45
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Cape Cod: Explorer Kayak Tour

Cape Cod: Explorer Kayak Tour

$77
per adult
Cape Cod: Explorer Kayak Tour
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Oak Bluffs

Oak Bluffs Hotel Deals

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
$570 nightly
The price is $636 total per night from Jul 14 to Jul 15
$636 total
Jul 14 - Jul 15
Total with taxes and fees
9.4/10 Exceptional! (1,011 reviews)
"Nice hotel - though be aware no elevator and our room was on the 4th floor - travelled light and just 2 nights so it was ok. No morning coffee service beyond a kerige which was a bummer"

Reviewed on Jul 11, 2026

Summercamp
MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue Oak Bluffs MA
$338 nightly
The price is $378 total per night from Jul 16 to Jul 17
$378 total
Jul 16 - Jul 17
Total with taxes and fees
8.8/10 Excellent! (863 reviews)
"We stayed here last week, 2 adults and 2 teenagers- all women. We felt very safe and comfortable here, that’s one of the first things we look for as we travel quite a bit and don’t experience that everywhere. We had a double queen room and they put us in a corner room. I can’t say enough about how ..."

Reviewed on Jul 12, 2026

MV Surfside Hotel
Pequot Hotel

Pequot Hotel

3 out of 5
19 Pequot Avenue Oak Bluffs MA
$399 nightly
The price is $446 total per night from Jul 14 to Jul 15
$446 total
Jul 14 - Jul 15
Total with taxes and fees
9.4/10 Exceptional! (602 reviews)
"The staff was very nice and helpful. The room wasn’t as clean as expected but I didn’t feel like it was just dirty. Pretty pricey for a room with 3 twin beds and small bathroom. But I think that’s the going price of lodging on Martha’s Vineyard."

Reviewed on Jul 8, 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.

Find the Best Oak Bluffs Vacation Packages

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.

Oak Bluffs Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Martha's Vineyard Airport (MVY)
Population
3,800
Max Temp Winter
40ºF
Max Temp Summer
70ºF
Top Sights
Inkwell Beach, Old Silver Beach and Falmouth Heights Beach

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Frequently asked questions

How much does an Oak Bluffs vacation package cost?
You can snap up a vacation package to this destination from $791 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.

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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.