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“The perfect long weekend for Vineyard first-timers” 5 of 5 stars
Review of The Dockside Inn

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The Dockside Inn
2.5 of 5 Small Hotel   |   9 Circuit Ave Extension, Oak Bluffs, Martha's Vineyard, MA 02557   |  
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November Special Pricing
Ranked #4 of 16 Oak Bluffs B&B and Inns
Philadelphia
Contributor
15 reviews 15 reviews
11 hotel reviews
Reviews in 11 cities Reviews in 11 cities
11 helpful votes 11 helpful votes
“The perfect long weekend for Vineyard first-timers”
5 of 5 stars Reviewed July 22, 2013

My fiance and I traveled to Martha's Vineyard for the first time over the first weekend in May 2013. I had read about the Dockside Inn in a travel guide, and looked at some of these reviews, and the price, before we decided to book it--and I am SO GLAD that we did. What a great little place! I love old houses (one of my little "someday" dreams is to have a veranda) and this place fulfilled everything I could have wanted in a trip like this. We had Room 20, which I highly recommend. It's at the corner of the second floor and has a full window view. We saw the neighbors out on their balcony, but they seem pretty used to having guests and we lowered the privacy screen when we needed to. Otherwise, check-in and check-out was a breeze. We especially liked the snacks kept in the back room for guests during the day--more than once those granola bars saved my life.

Like I said, it was early May, so the first day we got there was FREEZING. The weather improved with each day, though, so we were able to rent bikes from the place next door and ride to and from Edgartown along the beach path.

I would say that for the time of year, the value of the room was excellent. We actually loved the place so much that we checked out prices for the rest of the summer, which we can't swing just yet--but they go down again in the fall, so who knows, we might have another Vineyard weekend after all. We didn't bring a car with us, but the Dockside is in such a great location that we were able to get a bus anywhere we wanted to go--even Menemsha, although it did take a full day to explore that side of the island. We didn't mind that there is no "breakfast," as we were able to walk up the street to Linda Jean's and Slice of Life.

Just a note: if you travel before the ferry starts running from Woods Hole to Oak Bluffs, you'll dock in Vineyard Haven but it was super easy to catch the bus to Oak Bluffs if you don't bring a car.

  • Stayed May 2013, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 5 of 5 stars Service
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345 reviews from our community

Traveler rating
    279
    57
    6
    3
    0
See reviews for
68
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Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    4.5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (124)
Date | Rating
  • English first
  • French first
  • Any
English first
2 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed July 18, 2013

My husband and I just finished a mini vacation at The Dockside Inn. The Dockside is a charming Inn with impeccably clean rooms and amazing service. The staff was super friendly and eager to offer sight seeing and dining suggestions. The Inn is in a prime location with many restaurants and shops within walking distance. Our room was nicely decorated and the bed was very comfortable. My personal favorite was the rocking chairs on the deck and seating outside our room. Very relaxing ambiance which allowed us to take in the local atmosphere. Wonderful memories made and we cannot wait to return to The Dockside.

  • Stayed July 2013
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Astoria, New York, United States
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed July 17, 2013

In the Vineyard pricing structure, Dockside Inn falls mid-range. But in overall service, they approach the highest end. Amazing, friendly staff, super clean rooms, all-day free snacks and cold water, personalized activity recommendations, "Loomis" the virtual concierge (a real islander who texts recommendations!), "Champagne Fridays," an involved and present owner. They take care of even the small details - for example, a single black face cloth for makeup removal to avoid stains.

Room Tip: The water view rooms don't have that much water view. Save a few bucks by sleeping on the back...
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  • Stayed July 2013, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Schuylerville, New York, United States
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed July 15, 2013

My Sweetie & I have been making annual visits to the Dockside for eight years now. We always loved the Victorian charm & ambiance, but the new owners have truly "kicked it up a notch"! Fully renovated rooms, beautiful sea shore decor; elegant yet comfortable in every respect. " Our room" - yes we reserve the same one every year - faces the harbor and affords a perfect view of the lively goings-on. Two thumbs up to the recently added &/or upgraded amenities, which now include a breakfast/ snack room open all day, complete with Keurig coffee machines, bottled water, fruit, snacks, ice pops ... even - my favorite - two candy/ gum ball machines that don't require quarters! :)
Highly recommend this charming inn ...just don't book our room for the 4th of July weekend! We'll be in residence!!

  • Stayed July 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Malden, Massachusetts
1 review
2 helpful votes 2 helpful votes
4 of 5 stars Reviewed July 12, 2013

1) Location: Right off the ferry, immediately next to all the rentals (car/moped/bike) and the harbor-side bars and restaurants, and walking distance from everything in OB.
2) Amenities: Air-conditioned rooms, nice bathrooms, hot tub, porches, light breakfast/snack bar available throughout the day (with bottled water, granola bars, fruit, popsicles, coffee/tea). Honestly, didn't even use the Inn's "Ask Loomis" service - we just wandered / used Yelp / read TripAdvisor. And the bed was fantastically comfortable. We slept like the dead.
3) Staff: Incredibly friendly/helpful/welcoming. I forgot contact lens solution, and the attendant offered to drive my wife and I to the next town over (where there was the ONLY shop which sold contact lens solution after 9 PM). Top-notch customer service!

Room Tip: Get a room with a view of the harbor and access to the porch! Enjoy an evening sitting out on the p...
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  • Stayed July 2013, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 3 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Boston, Massachusetts
Senior Contributor
44 reviews 44 reviews
16 hotel reviews
Reviews in 16 cities Reviews in 16 cities
24 helpful votes 24 helpful votes
5 of 5 stars Reviewed July 8, 2013

You really couldn't ask for more. Great location, walking distance to everything in OB. The vintage rolls will take you to most places. You get beach chairs, towels, coolers, water, ice, all day coffee/tea and snacks! We thought we booked rooms with 2 twins, ended up with one full size. It was snug but we made do. I highly recommend this place. All the little perks make it worth while.

Room Tip: Do not stay in Room 3 or 4. 3 is a corner room on the first floor right next to a bike rental and so...
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  • Stayed July 2013, traveled with friends
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 3 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Needham, Massachusetts
1 review
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed July 8, 2013

They say location, location, location, but honestly even with the great location (right off the ferry, walking distance to everything!) I would say location was at the bottom of all the great reasons to stay at The Dockside Inn. From the minute we walked into the lobby I could tell I really liked this place. Everything looked brand new, very clean, inviting, and the staff was genuinely there to assist and make your stay better. The "snack room" has everything you could possibly want, all complimentary... coffee, icecream, yogurt, water, fresh baked cookies in the afternoon, hot homemade banana bread at breakfast... I'm sure I'm leaving 1/2 the offerings out. They're very family friendly and provided everything you would want to bring to the beach... towels, toys for kids, beach chairs, again all complimentary. When we inquired at the front desk about a taxi, they said they could provide us with car service. What I wasn't expecting was that a 57' Rolls Royce would be waiting for us to take us whereever we wanted to go. The owner is very hands on and a great guy that is truly dedicated to ensuring that his guests have a great experience. We will absolutely be back again and I wouldn't think of staying anywhere else.

  • Stayed July 2013, traveled with family
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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Additional Information about The Dockside Inn

Address: 9 Circuit Ave Extension, Oak Bluffs, Martha's Vineyard, MA 02557
Phone Number:
Location: United States > Massachusetts > Martha's Vineyard > Oak Bluffs
Amenities:
Beach Free High Speed Internet ( WiFi ) Free Parking Kitchenette Suites
Hotel Style:
Ranked #4 of 16 B&Bs / Inns in Oak Bluffs
Price Range (Based on Average Rates): $
Hotel Class:2.5 star — The Dockside Inn 2.5*
Number of rooms: 21
Official Description (provided by the hotel):
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 21 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! ... more   less 
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Also Known As:
The Dockside Hotel Oak Bluffs
The Dockside Inn Oak Bluffs, MA - Martha's Vineyard

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