Oak Bluffs Vacations from $325

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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
Save 100% on your flight
Price was $472, price is now $325 per person
$325
per person
Jan 16 - Jan 19
found 8 hours ago
Roundtrip flight included
Philadelphia (PHL) to Vineyard Haven (MVY)
18/10 Exceptional! (605 reviews)
Love the stay, w I’ll definitely stay again!

Reviewed on Oct 26, 2025

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
Save 100% on your flight
Price was $508, price is now $359 per person
$359
per person
Jan 16 - Jan 19
found 8 hours ago
Roundtrip flight included
Philadelphia (PHL) to Vineyard Haven (MVY)
18.4/10 Exceptional! (161 reviews)
Beautifully remodeled. Quiet. It has a common area with kitchen and living room space. Several entrances. Plenty of parking. Easy check in.

Reviewed on Oct 9, 2025

Morgan Hotel

Morgan Hotel

2.5 out of 5
Price was $476, price is now $364 per person
$364
per person
Jan 16 - Jan 19
found 8 hours ago
Roundtrip flight included
Philadelphia (PHL) to Vineyard Haven (MVY)
17.2/10 Exceptional! (193 reviews)
No staff at site, instructions for check-in unclear and confusing, rooms are fine, but way too expensive for what you are paying, you are mostly paying for location of the hotel, not your room

Reviewed on Nov 21, 2025

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

3 out of 5
Price was $500, price is now $402 per person
$402
per person
Jan 16 - Jan 19
found 8 hours ago
Roundtrip flight included
Philadelphia (PHL) to Vineyard Haven (MVY)
16.8/10 Exceptional! (593 reviews)
Courteous staff. Tub fixtures need upgrading. Bed could have been firmer.

Reviewed on Oct 28, 2025

Harbor View Hotel

Harbor View Hotel

5 out of 5
Price was $559, price is now $467 per person
$467
per person
Jan 16 - Jan 19
found 8 hours ago
Roundtrip flight included
Philadelphia (PHL) to Vineyard Haven (MVY)
17.6/10 Exceptional! (1,000 reviews)
Great staff. Friendly , beautiful hotel , scenic views and wrap around porch.

Reviewed on Nov 9, 2025

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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 seaside, or simply savor its wineries.

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 Harbor

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 seafood restaurants.

Oak Bluffs Harbor

What to do in Oak Bluffs

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

$50
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
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
9.2/10 Wonderful! (1,002 reviews)
Great location in Oak Bluffs - near a shuttle shop, lots of great shopping & restaurants. Room was nice size and room service was daily.

Reviewed on Nov 15, 2025

Get rates
Summercamp
Morgan Hotel

Morgan Hotel

2.5 out of 5
9 Healy Way Oak Bluffs MA
$167 nightly
The price is $187 total per night from Dec 10 to Dec 11
$187 total
Dec 10 - Dec 11
Total with taxes and fees
8.4/10 Very Good! (195 reviews)
Great little hotel. All communication is done via texting. There is no one on site at this hotel. However it’s a great little hotel near restaurants and bars.

Reviewed on Nov 3, 2025

Morgan Hotel
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Oak Bluffs MA
5.4/10 (21 reviews)
The place was exactly as listed. It is an older house but very clean conditions. I just think they need to supply it better you definitely need a car. There was no coffee or anything in the house. You have to bring everything.

Reviewed on Sep 16, 2025

Get rates
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
See all 3,008 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 $325 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.