Oak Bluffs Vacations from $629
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Inn on Main
$636
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
New York (NYC) to Hyannis (HYA)
10/10 Exceptional! (79 reviews)
Very accommodating hosts , Dave & Ruta. Delicious 2 course breakfast.Room was clean, very comfortable and great amenities. Hosts were very helpful regarding dining and touring ideas. Highly recommend
Reviewed on Aug 8, 2026
Faraway Martha's Vineyard
$1,735
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Vineyard Haven (MVY)
9/10 Wonderful! (1,001 reviews)
I enjoyed my stay in the Chappy House – Room 409, a suite with its on entrance from the outside. It was very well appointed and similar to a spacious one bedroom apartment without the kitchen. Must be capable of maneuvering stone pathways and steps to access it. Very nice for a long-term stay. I’d be interested in purchasing one! (Luxury vinyl plank flooring needs repairing in one hallway spot — barely noticeable.) 🙂
Reviewed on Aug 20, 2026
The Franklin Hotel Martha's Vineyard
$1,682
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Vineyard Haven (MVY)
9/10 Wonderful! (203 reviews)
Great place to stay. Very nice and private room. We stayed in room 19 and it had a private patio with a kitchenette in our room. Place was easy to find and had plenty of parking. Would recommend again
Reviewed on Aug 25, 2026
Morgan Hotel
$1,722
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Vineyard Haven (MVY)
8.6/10 Excellent! (253 reviews)
I enjoyed my one night stay at the Morgan Hotel, previous to my arrival I received communication via text to give me the instructions of how to check-in. The instructions were clear and concise and easy to follow. My room was nice and clean it had a microwave and there were plenty towels and I received a complimentary beach bag and water bottles. The amenities offered were super convenient some of which included the cutest little ice machine, coffee, plates, plasticware, cups, etc. Housekeeping staff were very pleasant and accommodating and there were plenty of nearby dining and shopping options. Overall it was a great experience and I would definitely stay there again, I wholeheartedly recommend the Morgan Hotel.
Reviewed on Aug 27, 2026
Stay near popular Oak Bluffs attractions
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.
Oak Bluffs Harbor
9.2/10 (510 reviews)
Oak Bluffs Harbor buzzes with maritime energy, where boats bob alongside waterfront shops and seafood restaurants. Secure a slip in advance during summer to experience the vibrant heart of Martha's Vineyard.
Photo by Fun Travelog
Oak Bluffs Town Beach
9.4/10 (134 reviews)
This historic beach has served as a beloved gathering spot for African American families for generations. Enjoy the calm waters just steps from Oak Bluffs' charming downtown shops and restaurants.
Ocean Park
9.2/10 (99 reviews)
This 7.5-acre green space showcases a historic bandstand surrounded by Victorian homes with views of Nantucket Sound. Summer evenings come alive with concerts and the spectacular August fireworks display.
Flying Horses Carousel
8.6/10 (106 reviews)
America's oldest operating platform carousel (1876) features hand-carved wooden horses with real horsehair manes. Catch a brass ring for a free ride on this National Historic Landmark.
Circuit Avenue
9.2/10 (82 reviews)
Circuit Avenue pulses as the heart of Oak Bluffs, lined with boutiques, eateries, and entertainment venues. Stroll this vibrant Martha's Vineyard hub for island-inspired shopping and fresh seafood dining.
Farm Neck Golf Club
8.2/10 (16 reviews)
This championship golf course blends farmland, woodland, and coastal views of Nantucket Sound into a memorable 18-hole experience. Reserve your tee time early to play where the fairways meet the sea.
Oak Bluffs Public Library
7.8/10 (27 reviews)
After visiting Oak Bluffs Public Library, make a plan to see the other sights and activities in Oak Bluffs. Wander the beautiful beaches and waterfront in the area.
What to do in Oak Bluffs
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
$50
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
$50
per traveler
Oak Bluffs Hotel Deals
Summercamp
70 Lake Avenue Oak Bluffs MA
$273 nightly
$305 total
Sep 27 - Sep 28
Total with taxes and fees
MV Surfside Hotel
7 Oak Bluffs Avenue Oak Bluffs MA
$289 nightly
$323 total
Sep 1 - Sep 2
Total with taxes and fees
Morgan Hotel
9 Healy Way Oak Bluffs MA
$314 nightly
$351 total
Sep 27 - Sep 28
Total with taxes and fees
8.6/10 Excellent! (257 reviews)
"I enjoyed my one night stay at the Morgan Hotel, previous to my arrival I received communication via text to give me the instructions of how to check-in. The instructions were clear and concise and easy to follow. My room was nice and clean it had a microwave and there were plenty towels and I received ..."
Reviewed on Aug 27, 2026
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 |
More vacations you might like
Frequently asked questions
How much does an Oak Bluffs vacation package cost?
You can snap up a vacation package to this destination from $629 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
Explore a world of travel with Expedia
- Beach Hotels in Falmouth
- Oceanfront Hotels in Martha's Vineyard
- Mashpee Hotels
- Marriott Hotels & Resorts in Martha's Vineyard
- B&B in Vineyard Haven
- Apartments in Oak Bluffs
- Hotels near Inkwell Beach
- Falmouth Hotels
- Oak Bluffs Hotels
- Pet-Friendly Hotels in Oak Bluffs
- B&B in Oak Bluffs
- Oceanfront Hotels in Cape Cod
- Edgartown Hotels
- Cheap Hotels in Martha's Vineyard
- Hyannis Hotels
- Cheap Hotels in Oak Bluffs
- Nantucket Hotels
- Woods Hole Hotels
- All-Inclusive Resorts in Cape Cod
- New Bedford Hotels
- Hotels with Restaurants in Oak Bluffs
- Vineyard Haven Hotels
- Beach Hotels in Oak Bluffs
- Plymouth Hotels
- Flights to Oak Bluffs
- Flights from New York (LGA) to Vineyard Haven (MVY)
- Flights from Washington (DCA) to Vineyard Haven (MVY)
- Flights from Hartford (BDL) to Vineyard Haven (MVY)
- Flights from San Francisco (SFO) to Vineyard Haven (MVY)
- Flights from New York (JFK) to Hyannis (HYA)
- Flights from New York (LGA) to Nantucket (ACK)
- Flights from Newark Liberty Intl. Airport (EWR) to Vineyard Haven (MVY)
- Flights from Los Angeles (LAX) to Vineyard Haven (MVY)
- Flights from Boston (BOS) to Vineyard Haven (MVY)
- Flights to Cape Cod
- Flights from Boston (BOS) to Nantucket (ACK)
- Flights from New York (JFK) to Vineyard Haven (MVY)
- Flights to Martha's Vineyard
- Flights to Nantucket Island
- Flights from Atlanta (ATL) to Vineyard Haven (MVY)
- Flights from Baltimore (BWI) to Vineyard Haven (MVY)
- Flights from Raleigh (RDU) to Vineyard Haven (MVY)
- Flights from Philadelphia (PHL) to Vineyard Haven (MVY)
- Flights from White Plains (HPN) to Vineyard Haven (MVY)
- Flights from Chicago (ORD) to Vineyard Haven (MVY)
- Flights from Martha's Vineyard
- Edgartown Vacations
- Eastville Beach
- Oak Bluffs Public Library
- Island Cove Adventures
- Felix Neck Wildlife Sanctuary
- Martha's Vineyard Film Center
- Vineyard Haven Vacations
- Nobska Lighthouse
- Island Queen Ferry
- Bend in the Road Beach
- Lighthouse Beach
- Circuit Avenue
- South Cape Beach State Park
- Visit Oak Bluffs
- Trinity Park Tabernacle
- Chappaquiddick Graveyard
- Gus Ben David's World of Reptiles and Birds Park
- Visit Falmouth
- Tisbury Town Hall & Katharine Cornell Memorial Theater
- Joseph Sylvia State Beach
- Flying Horses Carousel
- Visit Hyannis Port
- Farm Neck Golf Club
- Visit Vineyard Haven
- Visit Martha's Vineyard
- Inkwell Beach
- Martha's Vineyard Chamber of Commerce
- Dr Daniel Fisher House
- East Chop Light
- Tisbury Town Beach
- Martha's Vineyard Museum
- Visit Edgartown
- Visit Woods Hole
- Nantucket Vacations
- Surf Drive Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
