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Oak Bluffs

Welcome to Oak Bluffs, where pastel cottages dance along the shore and the vibrant boardwalk buzzes with life! Dive into local shops, savor fresh seafood, and don’t miss the stunning Flying Horses carousel—America's oldest! Explore the natural beauty of nearby beaches, and kick back during sunset with a slice of island charm. Adventure awaits in this Martha's Vineyard gem!

From the Community

Recommendations

Outdoor4.7/5

Ocean Park

Welcome to Ocean Park, the crown jewel of Oak Bluffs! This picturesque park, edged by sandy beaches and charming Victorian cottages, is perfect for sun-soaked picnics or a scenic stroll. Don’t miss the iconic Flying Horses Carousel nearby! With its lush greenery and vibrant ocean views, it’s a delightful spot to embrace the island's charm. Grab your shades and explore!

Outdoor4.5/5

Inkwell Beach

Renowned for its picturesque sands and vibrant atmosphere, Inkwell Beach in Oak Bluffs is a historic destination celebrated for its rich cultural heritage and stunning ocean views, making it a must-visit for beach lovers.

Landmark4.7/5

Martha's Vineyard Camp Meeting Association

Are you ready for an enchanting getaway? Look no further than Martha's Vineyard Camp Meeting Association! Nestled within Oak Bluffs, MA, this charming park offers a delightful escape for all travelers. Immerse yourself in the whimsical Victorian cottages, enjoy lively community events, and indulge in delicious local cuisine. With its idyllic location, MCCMA is the perfect spot for a memorable vacation.

Landmark4.7/5

Joseph Sylvia State Beach

Renowned for its picturesque sandy shores and vibrant sunsets, Joseph Sylvia State Beach offers a serene escape with stunning views, making it a must-visit destination for beach lovers on Martha's Vineyard.

Landmark4.5/5

East Chop Lighthouse

East Chop Lighthouse, perched on a scenic bluff in Vineyard Haven, offers stunning ocean views and a charming historic structure, making it a must-visit landmark for nature lovers and history enthusiasts alike.

Eat$$$$$4.4/5

Atria

Welcome to Atria, where culinary dreams become reality! Located on vibrant Main St, Edgartown, this foodie paradise boasts a mouthwatering menu that showcases fresh seafood, locally sourced ingredients, and creative flavors. Indulge in their famous lobster rolls, sip on expertly crafted cocktails, and soak up the charming atmosphere of this coastal gem. Get ready for a taste sensation like no other!

Eat$$$4.5/5

Offshore Ale Co

Eat$$$4.3/5

Linda Jean's Restaurant

Eat4.4/5

The Sweet Life Café

Renowned for its homemade pastries and cozy atmosphere, The Sweet Life Café in Oak Bluffs offers a delightful culinary experience, making it a cherished destination for locals and tourists alike.

Eat$$$4.5/5

Back Door Donuts

Welcome to Back Door Donuts, the hidden gem of Oak Bluffs! Located at 1-11 Kennebec Ave, this quirky bakery serves up scrumptious donuts that will blow your taste buds away. From classic flavors like glazed and chocolate to unique creations like maple bacon, there's something for everyone. Don't miss their famous late-night batches, perfect for satisfying those midnight cravings. A must-visit for donut aficionados!

Eat4.6/5

Enchanted Chocolates

Nestled in charming Oak Bluffs, Enchanted Chocolates is a delightful haven for sweet enthusiasts! With its whimsical decor and heavenly aroma, every visit feels like stepping into a chocolate wonderland. Indulge in handmade truffles, luscious bars, and decadent caramels, all crafted with love. Perfect for a sweet souvenir or a treat after exploring the island—guilty pleasure alert!

Eat$$$4.6/5

The Barn Bowl & Bistro

Eat$$$4.4/5

Espresso Love

Espresso Love, nestled in the charming streets of Edgartown, MA, is a caffeine oasis that will tickle your tastebuds with joy. This lively coffee shop encompasses the ultimate vacation vibes, serving up silky smooth espressos and aromatic blends that will jolt your senses to life. So, grab a cup of pure bliss at Espresso Love and let the adventure begin!

Stays

Stay$$$4.7/5

The Oak Bluffs Inn

<h2>Historic Charm</h2> The Oak Bluffs Inn in Oak Bluffs offers a 4-star experience within a historic building. Guests enjoy a beautiful garden and terrace, complemented by free WiFi in public areas. <h2>Comfortable Accommodations</h2> Rooms feature air-conditioning, private bathrooms, and city views. Additional amenities include balconies, kitchenettes, and work desks, ensuring a pleasant stay. <h2>Dining Experience</h2> A variety of breakfast options are available, including continental, à la carte, vegetarian, vegan, and gluten-free. Guests can also enjoy a lounge, outdoor fireplace, and picnic area. <h2>Prime Location</h2> Located 8 km from Martha's Vineyard Airport and a 6-minute walk to Oak Bluffs Town Beach. Nearby attractions include Edgartown Lighthouse (10 km) and Kennedy Studios (5 km). Highly rated for its friendly host.

Stay$$4.55/5

Pequot Hotel

Nestled among the charming cottages of Oak Bluffs, Martha's Vineyard, this Victorian-style hotel is only steps from the island's main attractions and offers friendly, personalised service along with cosy accommodations. Start each morning at the Pequot Hotel with delicious fresh baked muffins and a free continental breakfast. Relax in the afternoon on the spacious porch with a cup of tea and fresh biscuits. After a long day of sightseeing, take advantage of free wireless internet access before going to sleep. Discover the unique shops, art galleries and gourmet restaurants Martha's Vineyard is famous for, located only steps from the Pequot. Beautiful beaches as well as scenic cycle paths, fishing and sailing are also easily accessible.

Stay$$$4.4/5

Summercamp

This historic Martha’s Vineyard hotel, Summercamp, is located in Oak Bluffs and offers oceanfront views. Featuring a game room and common lounging areas, the hotel is steps away from the beach. Housed in a renovated 1879 property, it is equipped with modern amenities. Guests have access to iPads loaded with area information and on-site hospitality centres. Rooms are equipped with smart TVs with Apple TV, USB charging outlets and radios. Some rooms come with seating areas and/or refrigerators. Guests are provided with robes and complimentary toiletries as well. Free Wifi, a camp canteen with snacks and a 24-hour front desk are available at Summercamp. Coffee makers are provided in the suites and cottage suites. Free daily housekeeping services are also available. Farm Neck Golf Club is 3.7 km away. There are several fine dining and casual dining options close to the property as well. The Oak Bluffs Ferry is 5 minutes’ walk away.

Stay4.7/5

The Dockside Inn

Stay4.4/5

Mansion House Inn on Martha's Vineyard

Welcome to the Mansion House Inn on Martha's Vineyard! Located at 9 Main St in Vineyard Haven, this charming inn is your perfect island getaway. With its cozy rooms, delightful views, and convenient location, you'll feel like a true explorer. Whether you're enjoying the nearby shops or diving into the island's rich history, the Mansion House Inn will make your stay unforgettable.

Stay4.2/5

Martha's Vineyard Surfside Hotel

Nestled in scenic Oak Bluffs, Martha's Vineyard Surfside Hotel offers breathtaking ocean views, cozy beachfront accommodations, and easy access to iconic local attractions, making it a perfect getaway for relaxation and adventure.

Stay

Colonial Inn-Martha's Vineyard

Things To Do
Provided by

5/5

Electric Bike Tours on Martha Vineyard

Explore the beauty of Martha's Vineyard on an electric bike tour designed just for you. It offers unique experiences tailored to your interests: secluded beaches, historic farms, the iconic Gingerbread Houses, and more. Let us take you there. Choose 4-6 hour private tour, where every detail is curated to ensure you see a few of the island's gems: lighthouses, Downtown Edgartown, Oak Bluffs, Chappaquiddick. Or call us and inquire about our 3-day Tour De L'ile for an in-depth adventure across the island's six towns. All tours include e-bike use, helmet, water, snacks, and admission to select attractions. - Explore top attractions like the Campground Cottages in Oak Bluffs and Chappaquiddick Island. - Private tours available for groups up to six riders, ensuring a personalized experience. If you have more riders, give us call a week in advance and we will try to accommodate you.

$250.00

5/5

Self Guided Walking Tour of Oak Bluffs Marthas Vineyard

Unearth the charm of Oak Bluffs on this self-guided walking tour, where the rich history and vibrant culture of this New England seaside town come alive. Wander among whimsical gingerbread cottages, enjoy stunning harbor views, and learn how this area evolved from a Methodist camp meeting site to a celebrated resort. This tour highlights the unique blend of architecture, community spirit, and African American heritage that defines Oak Bluffs, making it a delightful exploration of summer memories and local stories. — Discover the distinctive Victorian architecture and intricate cottages — Explore the historical significance of Oak Bluffs as a cultural hub — Enjoy scenic ocean views and shaded park paths during your stroll — Perfect for history buffs and those seeking a unique coastal experience

$9.99

4.7/5

12 h

Boston: Martha's Vineyard ICONIC Small Group Day Escape w/Ferry

Leave Boston behind and set out on a full-day journey to Martha's Vineyard, one of New England's most beloved islands. This experience blends a scenic ferry crossing, historic seaside villages, and the laid-back charm of island life. Board the Island Queen ferry in Falmouth and cruise across Nantucket Sound to Oak Bluffs, where colorful gingerbread cottages surround the historic Tabernacle at the Martha's Vineyard Camp Meeting Association. Enjoy time to explore the island's most iconic spots, with an optional sightseeing bus tour covering the Flying Horses Carousel, the refined harbor town of Edgartown, Gay Head Light atop the dramatic Aquinnah cliffs, and Nobska Point Lighthouse. Return via the Steamship Authority ferry from Woods Hole, rounding out a full day of coastal views, ocean breezes, and authentic New England island character.

$108.00

4.6/5

3 h

Best of Martha's Vineyard 3 hour Full-Island Tour

Perfect tour to see all six towns on Martha's Vineyard in 3 hours, and to stop and get out to see the the beautiful seaport of Menemsha and the cliffs in Aquinnah. Customers will be engaged by great, "five star" local guides providing narration about the history, culture, celebrities, lighthouses, beaches, Jaws, gingerbread cottages, whaling captain's homes, and much more. Conducted in very nice, comfortable, air-conditioned, high top Ford Transit vans with large windows.

$65.00

4.6/5

3 h

#1 Best 3hr Martha's Vineyard shared Island Tour from Oak Bluffs

Experience our famous 3-hour full Island tour for a budget friendly rate! Our tour drivers - native Islanders & long-time "wash-a-shores" have years of tour driving experience and the best reviews to show it! This 3-hour tour will introduce you to our 100 square mile island by giving you the history, both past and present, of our 6 unique towns. In all, 2 ½ hours of the tour is narrated, and you'll have a stop at the beautiful Cliffs of Aquinnah. Top highlights on this tour include Oak Bluffs, Edgartown, Vineyard Haven, Aquinnah, West Tisbury, Chilmark, and Menemsha. So join us in our comfortable air-conditioned vans & get ready to make memories for a lifetime - your Martha's Vineyard tour! (Children under 10 excluded from this tour.)

$70.00

4.5/5

12 h

Boston to Martha's Vineyard Day Trip with Optional Island Tour

We are proud to offer Boston's ORIGINAL Martha's Vineyard Day trip. Since 2011 we have been Boston's #1 day trip service to the island. Our professional guides, approved Boston Hotel pickups and newer air-conditioned mini-coaches will help provide you with the personalized passenger experience that our guests truly deserve. Transportation to the island has never been this easy! You will also receive complimentary snacks, bottled water, island guidebooks and a discount card with some island perks! Once on the island, explore on your own or upgrade with our 3 hour fully narrated island tour. Let us help you Discover Martha's Vineyard!

$129.00

4.1/5

3 h

Martha Vineyard Bus Tour

Please Note: During the summer of 2026, our family experienced a devastating medical emergency involving multiple immediate family members. A small number of tours were canceled on very short notice while we handled those circumstances. We sincerely apologize to those affected and are deeply grateful for the kindness and understanding shown by so many guests during this incredibly difficult time. We are, the only ones have four stops to get off the bus. We also offer a lot of amenities that no other tour offers. The tours keep you fully engaged and all we require is for you to be curious! We will not disappoint, what makes us entirely different is that we have a screen at the front of the bus that shows what certain sites looked like in the days of yore. The All Island Bus Tour takes you on an adventure you will never forget. Capture the beautiful vistas, the quaint little cottages, the amazing clay cliffs and everything in between.

$75.00

3.2/5

Oak Bluffs, Martha's Vineyard Audio Tour

Knockabout Travel takes you to Martha's Vineyard, with this self-paced audio tour of the most popular town on the island. Discover the origin story of how Oak Bluffs developed from its humble beginnings as a religious camp into a summer destination for business moguls, celebrities, and US Presidents. On the tour, we discuss the development of the Martha's Vineyard Camp Meeting Association, home to the "campground" and the famed gingerbread cottages. Learn how the area around Ocean Park and Circuit Avenue was developed with tourism in mind, and how that conflicted with the original Methodist campers. Along the route, you will be introduced to some of the finer points and lesser-known history of the town, as well as places to grab lunch or a drink. The tour is GPS guided with turn-by-turn directions and audio tracks that play automatically at the right time and place so you're free to simply enjoy the tour.

$12.99

Discovering Oak Bluffs: A Self-Guided Audio Tour

Discover how a small religious summer camp transformed into one of Martha’s Vineyard’s most popular island destinations on this walking tour through the town of Oak Bluffs. Starting in Ocean Park, you’ll follow the coast to Inkwell Beach before heading into the heart of the town. Along the way, you’ll hear its history and find out what makes this island paradise so alluring to everyone from the rich and famous, to curious Cape Cod vacationers that come for a day. Around Trinity Park, you’ll see Martha’s Vineyard Camp Meeting Association, its cottage museum, and the Tabernacle in Oak Bluffs which is a place of worship. After heading down Circuit Avenue, where I’ll show you the town’s famous Flying Horses Carousel, our tour will come to an end at the harbor. Whether you’re on the island for only a day, or calling Martha’s Vineyard home for the season, this tour is for anyone who wants to dig into Oak Bluffs’ past and enjoy its present.

$11.99

5/5

4 h

Private Guided Night Photography Tour on Cape Cod: 1-Photographer

One of the best times to see and and experience Cape Cod is after dark when the landscape is lit by starlight or moonlight. These times also give you the opportunity to visit and travel between destinations during hours that many people are asleep making these places quiet and serene. This tour is available for all experience levels. Night photography is a fantastic way to capture popular or "over shot" subjects in new ways. We'll use long exposure techniques and flashlights to create an immersive art experience. If you've never visited the Cape Cod area and are unsure of where the best subjects are, this tour ensures you get the best locations based on the sky conditions available. Choose between a moonlight or starlight(Milky Way) tour! Contact me for the date range you are available for more information on moon phase and sky information. Please contact me for availability before booking.

$425.00

5/5

2 h

Marthas Vineyard Luxury Tour (2hrs)

Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people (5 max) looking for a truly unique experience. Relax and enjoy this narrated tour as we drive along the scenic coast, stop for photos, talk about famous people, learn about local history, all while passing through the 3 down-island towns. For those travelers coming over for the day with limited time, who would like to see the down Island towns, this is the perfect tour.

$450.00

5/5

Boston Haunted History Self-Guided Walking Audio Tour

Traverse Boston’s oldest neighborhoods and hear about the lost souls still trapped within—from the poor, perpetually burning victims of a gas explosion in Boylston Station to a spectral woman in the Boston Common who tries to convince children to follow her into the dark. Walk through uneasy graveyards where the bodies have been moved, dug up, or lost altogether, and learn the stories of their unquiet dead. After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This is not an entrance ticket to attractions along the route. Check opening hours before your visit.

$14.99

5/5

2 h

Cape Cod Pirate Adventure Paddle Hunt and Battle

Families can enjoy a unique pirate-themed adventure on the serene waters of Cape Cod. This 2-hour journey invites young explorers aged 8 and up to paddle, engage in a lively water cannon battle against a rogue pirate, and uncover hidden treasures. Expert guides ensure safety while igniting excitement with interactive storytelling and teamwork. It's the perfect way to enjoy a day out of the water, all while connecting with nature and creating lasting memories together. Adventurers 2-7 are welcome to accompany an adult on their paddleboard.

$100.00

4.9/5

3 h

Private, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs)

-Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people (5 max) looking for a truly unique experience. -Relax and enjoy this narrated tour as we drive along the scenic coast, stop for photos, talk about famous people, learn about local history, all while passing through the 6 island towns. -For those travelers coming over for the day with limited time, who would like to see the whole island, this is the perfect tour.

$550.00

4.7/5

48 h

Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)

Get the full Massachusetts experience with this combo of walking and driving tours around Boston! You’ll find ten tours in one app - all highly entertaining, thoroughly researched and prepared by local guides. Self-Guided Tours are: 1- Boston Freedom Trail (Walking) 2- Harvard Square (Walking) 3- Boston Ghost (Walking) 4- Salem Witch Trials (Walking) 5- Boston Harborwalk (Walking) 6- Plymouth (Walking) 7- Cape Cod & Provincetown (Driving) 8- Cape Ann (Driving) 9- Battle of Lexington (Driving) 10- Martha’s Vineyard (Driving) This self-guided tour allows you to explore Boston’s historic wonders with maximum flexibility and value. After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want.

$49.99

4.3/5

Edgartown Martha’s Vineyard Self-Guided (GPS) Audio Walking Tour

Go at your own pace, anytime! It's your tour. On our historic walking tour of the Edgartown, you will see the iconic sights and secret gems including the whaling church, the oldest buildings, underground railroad locations, the Carnegie library, filming sights of Jaws, the lighthouse and much more. And I’ll tell you this town’s stories of the settlers, natives, whaling, ghosts, myths and legends, the Kennedy’s, it’s history and much more. Pro narration and production! Best deal in town :)

$9.75

4/5

Martha’s Vineyard Self-Guided Driving & Walking Audio Tour

Get ready to visit one of the greatest vacation spots in the USA, a favorite among celebrities and even presidents! Martha’s Vineyard is home to stunning beaches and coastline, picturesque little towns, and plenty of fun—but this GPS-guided driving tour with walking portions will also dig beneath the beautiful surface and into the island’s surprising history. Learn about the Wampanoag, the origin of the Vineyard’s famous “gingerbread houses,” and the lost language invented by the island’s residents! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

$14.99

2.8/5

2 h

Martha’s Vineyard Venture Scavenger Hunt

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

$20.00

144 h

MA Cape and The Island Tour

Experience the unsurpassed beauty of Cape Cod while discovering iconic sites and hidden scenes. This is Great Freedom Adventures’ backyard and we love sharing it with our guests. Unique for tours in the region, the six-day bike tour offers a wide-ranging exploration of many of the finest of Cape towns and includes both of the area’s celebrated islands – Nantucket and Martha’s Vineyard. Enjoy the discovery purely by bike and boat, at a pace that allows you to take it all in. All of the Cape Cod places you’ve been dreaming of visiting – or yearning to revisit – are waiting for you here, in one inspired itinerary.

$3,955.00

48 h

Martha's Vienyard full day tour with lunch

Tour apx time is 5-6 hr. Max 4 ppl. Price is per person. Originally inhabited by the Wampanoag people, Martha's Vineyard was known in the Massachusett language as Noepe, or "land amid the streams". In 1642, the Wampanoag numbered somewhere around 3,000 on the island. By 1764, that number had dropped to 313.[10] A smaller island to the south was named "Martha's Vineyard" by the English explorer Bartholomew Gosnold, who sailed to the island in 1602. The name was later transferred to the main island. It is the eighth-oldest surviving English place-name in the United States. English settlement began with the purchase of Martha's Vineyard, Nantucket, and the Elizabeth Islands by Thomas Mayhew of Watertown, Massachusetts from two English "owners". He had friendly relations with the Wampanoags on the island, in part because he was careful to honor their land rights. His son, also named Thomas Mayhew, began the first English settlement in 1642 at Great Harbor (later Edgartown, Massachusetts)