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9 Circuit Ave Extension, Oak Bluffs, Martha's Vineyard, MA 02557
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Traveller (238)
Room & Suite (77)
Dining (10)
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Tripadvisor gives a Travellers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.


#3 of 15 B&Bs / Inns in Oak Bluffs
Travellers' Choice
Get Away & Play. The Dockside Inn is Oak Bluffs hospitality & elegance at its best - built in 1989, the hotel has the conveniences of a new modern facility including 22 regular guest rooms. All rooms have Queen beds - some with two. All feature air conditioning, cable TV, in-room refrigerators, and free WiFi. All rooms are comfortably furnished for your vacation. Our location on the Oak Bluffs Harbor is just steps from restaurants, boutiques, beaches, boating, ferries, buses and so much more!
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Property amenities
Free parking
Free High Speed Internet (WiFi)
Hot bath
Snack bar
Non-smoking hotel
Pool / beach towels
Outdoor furniture
Sun loungers / beach chairs
Sun terrace
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Room features
Air conditioning
Wake-up service / alarm clock
Flatscreen TV
Complimentary toiletries
Room types
Ocean view
Non-smoking rooms
Family rooms
Good to know
Great View
Languages Spoken
730Reviews12Q+A100Room tips
Traveller rating
  • 612
  • 97
  • 16
  • 4
  • 1
Time of year
Traveller type
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Popular mentions
Hannah E wrote a review Nov 2021
1 contribution1 helpful vote
Incredibly kind staff, clean quiet and comfortable rooms. I even got a free bottle of champagne to have after my walk around east chop drive! Highly recommend staying here. Right in oak bluffs and a short 10min drive to neighboring towns.
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Date of stay: November 2021Trip type: Travelled solo
1 Helpful vote
Global29479072306 wrote a review Sep 2021
1 contribution
John at the Dockside provides great customer service! The wifi is strong which is key as other local businesses don’t have it. Service can be sketchy on the island. Beautiful inn in and in great location on the wharf close to everything. Thank you!
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Date of stay: September 2021Trip type: Travelled solo
kaycon165 wrote a review Jul 2021
Boston, Massachusetts25 contributions20 helpful votes
I can’t say enough good things about the Dockside! First of all, the location is perfect coming off of the ferry, a very short walk away. We arrived and they checked to see if the room was ready , which it was, so very easy check in. Room was immaculate. The next day we headed to the beach and they have all the necessities we needed: cooler, chairs, towels, etc.! The coffee/snack shack is stocked with all kinds of great snacks for the day, coffee in the morning. Plus the homemade cookies in the lobby in the afternoon is such a great treat. Staff is so friendly and accommodating! Will be back and will (and already have) tell all my friends!!
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Date of stay: July 2021Trip type: Travelled as a couple
1 Helpful vote
Kevin K wrote a review Jul 2021
Falmouth, Massachusetts47 contributions17 helpful votes
My wife and I stayed for 3 nights in July and had an absolutely wonderful experience at the Dockside Inn. The rooms were clean and the showers were great. I loved sitting on the porch and watching the people come by. It’s in a great location, right next to Oak Bluffs Harbor. My wife loved all of the shops that were super close. I parked our bicycles out back in a safe little area. There’s a back enclosed porch with snacks, and cold filtered water, a couple of Keurig machines and we’ll stocked Green Mountain coffee choices, ice creams, fruit, pop tarts, etc. A nice place. Beach stuff, they have coolers, an ice machine, beach chairs and umbrellas to borrow, which was great. There’s a new beach in Oak Bluffs between the harbor entrance and the Steamship Authority and it’s nice and it’s a 2 min walk from the hotel. The staff was great and very helpful. Mary, Maddie, Kevin, and John, everyone was polite, attentive and informative. We bicycled to Edgartown for a day, about 6ish miles each way. Lots of fun things and good places to eat in Oak Bluffs. And although it might seem somewhat busy around you it was quiet in our room and everything around closes down rather early by 10pm or so, so no worries there either. Good luck on your adventures.
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Date of stay: July 2021Trip type: Travelled as a couple
1 Helpful vote
James D wrote a review Jul 2021
Boston, Massachusetts2 contributions2 helpful votes
We just had another fantastic stay at the Dockside Inn. This place is sparkling clean and the staff is very kind and attentive. I recommend staying here any time you want or need to stay on the Island because, It's close to the ferries on Oak Bluffs. It's extra clean. It's very comfortable. The people are very nice and they really know the island. Outstanding amenities. Thanks John and crew for another great time. See you soon.
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Date of stay: July 2021Trip type: Travelled with family
1 Helpful vote
US$122 - US$189 (Based on Average Rates for a Standard Room)
the dockside hotel oak bluffs
United StatesMassachusettsMartha's VineyardOak Bluffs
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Frequently Asked Questions about The Dockside Inn
Which popular attractions are close to The Dockside Inn?
Nearby attractions include Martha's Vineyard Camp meeting Association (MVCMA) (0.4 km), Ocean Park (0.3 km), and Flying Horses Carousel (0.1 km).
What are some of the property amenities at The Dockside Inn?
Some of the more popular amenities offered include free wifi, free parking, and a hot tub.
Which room amenities are available at The Dockside Inn?
Top room amenities include air conditioning, a flat screen TV, and a refrigerator.
What food & drink options are available at The Dockside Inn?
Guests can enjoy a snack bar during their stay.
Is parking available at The Dockside Inn?
Yes, free parking is available to guests.
What are some restaurants close to The Dockside Inn?
Conveniently located restaurants include Back Door Donuts, The Red Cat Kitchen, and Biscuits.
Are there any historical sites close to The Dockside Inn?
Many travellers enjoy visiting Trinity Park Tabernacle (0.4 km).
Does The Dockside Inn have any great views?
Yes, guests often enjoy the harbour view available here.
Is The Dockside Inn accessible?
Yes, it offers reduced mobility rooms. For specific enquiries, we recommend calling ahead to confirm.