Oak Bluffs Vacations from $873
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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.
Inn on Main
$885
per person
Nov 25 - Nov 28
found 13 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hyannis (HYA)
10/10 Exceptional! (80 reviews)
Ruta and David were excellent hosts. The Inn is lovely and has a beautiful yard with outdoor seating. The rooms were very clean, spacious and well appointed. The breakfasts were outstanding. The Inn is in a great location for exploring the Cape. I would highly recommend a visit to the Inn on Main.
Reviewed on Sep 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.
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.
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.
East Chop Light
8.4/10 (34 reviews)
Perched on Telegraph Hill, this historic 1876 lighthouse offers sweeping views of Vineyard Sound. Visit at sunset to capture the iconic white tower silhouetted against Martha's Vineyard's colorful skies.
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.
What to do in Oak Bluffs
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
$50
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
$50
per traveler
Oak Bluffs Hotel Deals
Summercamp
70 Lake Avenue Oak Bluffs MA
$188 nightly
$215 total
Oct 29 - Oct 30
Total with taxes and fees
MV Surfside Hotel
7 Oak Bluffs Avenue Oak Bluffs MA
8.8/10 Excellent! (935 reviews)
"We loved our stay and will definitely be back"
Reviewed on Oct 7, 2026
Pequot Hotel
19 Pequot Avenue Oak Bluffs MA
$299 nightly
$342 total
Oct 9 - Oct 10
Total with taxes and fees
9.4/10 Exceptional! (630 reviews)
"We were pleasantly surprised at how nice the staff & GM were' and hotel teamwork made us feel comfortable, the island was beautiful and we would go back in a heartbeat, the ambience of the hotel with the flowers and the rocking chairs and decorations wonderful also the continental breakfast had a ..."
Reviewed on Oct 7, 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 |
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Frequently asked questions
What types of vacation packages are available in Oak Bluffs?
Oak Bluffs is a charming beach destination, and vacation packages can be tailored to several travel styles:
- Beach package: With Oak Bluffs primarily known for its beaches, many packages focus on easy access to the shore. For example, a stay at Summercamp, a 3.5-star property rated 8.8 out of 10 by travelers, places you about a 10-minute walk from Inkwell Beach.
- Family package: For those traveling with children, options like The Island Inn on Martha's Vineyard, rated 8.2 out of 10 by travelers, offer family rooms and an outdoor pool for relaxation and fun.
- Luxury package: Nearly all hotels in Oak Bluffs fall into the luxury tier, providing upscale amenities and services. You can find options like Summercamp, a 3.5-star hotel rated 8.8 out of 10 by travelers, offering a refined stay.
- Budget package: Value-focused travelers can find options such as The Attleboro House, rated 8.6 out of 10 by travelers, which includes free WiFi and is about a 10-minute walk from Inkwell Beach.
How can I save money on a Oak Bluffs vacation package?
When you bundle, you can save up to 30%*. To save money on a Oak Bluffs package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
How much does an Oak Bluffs vacation package cost?
An Oak Bluffs vacation package typically costs around $1,550 per adult for a weekend trip. Lower-priced options start around $1,100 per adult, while premium packages can reach up to $2,850.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How do I find cheap Oak Bluffs vacation package deals?
The cheapest Oak Bluffs vacation package deals can be as low as around $890 per adult for weekend trips. Separately, June typically has the lowest average monthly prices, around $1,570 per adult, for a 4-day trip, while July follows closely at around $1,730, for a 3-day trip. Bundling flights and hotel together also typically saves money on a weekend trip — nearly all Oak Bluffs packages include some savings versus booking separately, typically around $115 per adult. Longer, week-long trips can save even more, often around $250 per adult. Browse cheap vacation packages in Oak Bluffs on Expedia for current deals.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
What is the best time to go to Oak Bluffs?
The best time to go for an Oak Bluffs vacation package is during the summer months from June to August. These months are the most popular for travelers visiting Oak Bluffs, and they also offer some of the most competitive starting prices for packages.
What's included in an Oak Bluffs vacation package?
An Oak Bluffs vacation package lets you combine round-trip flights, hotel stays, and rental cars. Many hotels offer convenient beach access, allowing you to easily enjoy the shoreline.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
What's the best vacation package for Oak Bluffs?
For families, an Oak Bluffs vacation package with a stay at The Island Inn on Martha's Vineyard, rated 8.2 out of 10 by travelers, offers comfortable family rooms and an outdoor pool, making it a great choice for those traveling with children.Couples looking for a charming getaway might consider a package featuring Summercamp, a 3.5-star property rated 8.8 out of 10 by travelers. Located about a 5-minute walk from central Oak Bluffs, the property is often praised by travelers for its walkable location and fantastic staff.If you're seeking the best value, The Attleboro House, rated 8.6 out of 10 by travelers, provides a comfortable stay with free WiFi for around $270 per night. Travelers frequently highlight its lovely value and spotless overall impression.*Package availability and prices may change depending on dates and demand.
Is Oak Bluffs better suited for a beach vacation or a cultural trip?
Oak Bluffs is primarily a beach destination, offering travelers a classic New England coastal experience. Its shores, like Inkwell Beach and Oak Bluffs Town Beach, are known for minimal surf, making them ideal for swimming and wading. About half of the package hotels here offer ocean views, enhancing the beach vacation feel for your Oak Bluffs vacation.Beyond the beaches, an Oak Bluffs vacation package can also include a rich cultural and historical experience. Visitors can explore the unique "gingerbread cottages" of Wesleyan Grove, a National Historic Landmark, or ride the historic Flying Horses Carousel, the oldest platform carousel still in operation. The town also holds significant history as a welcoming vacation spot for African Americans since the 19th century.
What is the best time to book an Oak Bluffs vacation package?
Book your Oak Bluffs vacation package around 7 weeks in advance. It gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 3 and 15 weeks out.From June to August is the most popular months for Oak Bluffs packages, so booking earlier is advisable if you're traveling during these times.
What are the top things to do in Oak Bluffs?
An Oak Bluffs vacation offers a mix of beach relaxation and charming historic attractions:Browse and book things to do in Oak Bluffs on Expedia.
How many days do you need for an Oak Bluffs vacation?
Most Oak Bluffs vacation packages last around 3 days, with many travelers opting for weekend trips. This duration allows you to comfortably explore key attractions like Inkwell Beach, stroll along Circuit Avenue, and experience the historic Flying Horses Carousel.For those seeking a more extended Oak Bluffs vacation, nearly a third of travelers choose week-long trips, which provide ample time to visit more beaches, explore Martha's Vineyard Preservation Trust Historic Buildings, or take a day trip to other parts of the island.
Is Oak Bluffs a good destination for a weekend vacation?
Oak Bluffs is an excellent destination for a weekend vacation package. Most travelers choose weekend trips, making it a popular choice for a short getaway. In just a few days, you can enjoy the calm waters of Inkwell Beach, explore the shops and restaurants along Circuit Avenue, and take a nostalgic ride on the Flying Horses Carousel.While many travelers opt for longer stays to explore more of Martha's Vineyard, a focused Oak Bluffs vacation can still offer a fulfilling and relaxing experience over a weekend.
Do you need to rent a car in Oak Bluffs, or is public transport enough?
For an Oak Bluffs vacation package, you don't necessarily need to rent a car, especially if you plan to stay within the compact town center. Oak Bluffs is very walkable, allowing you to easily explore attractions like Circuit Avenue and Inkwell Beach on foot.The Martha's Vineyard Regional Transit Authority (VTA) operates local buses island-wide year-round, providing an affordable way to reach other towns and beaches. Taxis are also readily available, with stands near the harbor. However, for those looking to explore the wider island at their own pace, a rental car offers greater flexibility for your Oak Bluffs vacation packages with flights. You can also find bicycle and moped rentals for shorter distances, making Oak Bluffs beach vacation packages easy to navigate.
Are Oak Bluffs vacation package hotels conveniently located?
Oak Bluffs vacation package hotels are generally very conveniently located, often within easy reach of the town center and popular beaches. For instance, Summercamp is about a 5-minute walk from central Oak Bluffs and about a 10-minute walk from Inkwell Beach. Similarly, the Morgan Hotel is also about a 5-minute walk from central Oak Bluffs and just a 5-minute walk from Inkwell Beach.Even properties slightly further out, like The Island Inn on Martha's Vineyard, are still only about 1 mile from central Oak Bluffs and Inkwell Beach, making it easy to access the town's attractions and waterfront.
Can I change or cancel my Oak Bluffs vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Oak Bluffs vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Oak Bluffs vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Oak Bluffs vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Oak Bluffs?
To find last-minute vacation packages to Oak Bluffs, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Oak Bluffs vacation packages?
Free cancellation on a Oak Bluffs vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Oak Bluffs vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Oak Bluffs getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Oak Bluffs vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.
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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.