The Dockside Inn

We were very impressed with the Inn. The inn and the rooms were very cute, the location couldn’t be better and the solarium had all the essentially to keep you fueled, coffee, snacks, apple fritters, YUM! Victoria was the gal who helped us and could have been sweeter. We highly recommend this for your visit!

I was looking forward to a fall weekend stay at dockside but hurricane winds from Joaquin shut down ferry service from Falmouth so I called dockside and they were very cold and unbending with their policy of 21 days advance notice. I understand this policy — especially in summer months — but there is no way they would resell my room because you couldn’t get there from some ferries. They indicated woods hole ferry runs 365 days a year etc etc. Really — who wants to ride a ferry with such rough seas. Very disappointed in attitude/​service.

As a family of 5 traveling, it is rare that everyone is happy with any choice of accommodations, but everyone was beyond happy with the Dockside. We had a great time, loved the Inn, from the rooms to the common areas for relaxing, and will return in the future for sure. Treat yourself and visit!

I stayed here Memorial Day Weekend and I loved it. It was centrally located in Oak Bluffs near all the bars, restaurants, the ferry, etc. The owner was incredibly nice and greeted us when we got there 2 hours before check-​in (had we got there on time we would have also been greeted with a glass of champs). Our room was already ready and had been upgraded! The room was clean (and I own a cleaning company so I’m pretty picky) and had so many nice extras. I am a pillar at 5 star hotels and my expectations can be high. Ladies, have you ever stayed somewhere that provides you with makeup remover packets? This may have been a small gesture (that saves their towels), but it meant so much and made me so happy. They have a room with beach equipment that you can take (and bring back) if you want to have a beach day. Coolers, towels, etc. Another room with all sorts of free snacks from 7am — 10pm.
I loved this place and will definitely be staying there when in The Vineyard.

While trying to decide where to go for our 7^th wedding anniversary, we happened upon The Dockside Inn. We’ve wanted to go to Martha’s Vineyard but didn’t want to go during the busiest time of the year. After MUCH research, we settled on Oak Bluffs and The Dockside Inn. Before making my reservation, I called and spoke to John (I believe he is the owner). From the first conversation with him, I knew I picked the right place.
When we arrived, we were greeted by Lianne. She is a beautiful and friendly young woman who makes you feel right at home. Her warm smile and cheery attitude are just as nice as the décor. After not even 5 minutes, we were off to a short tour and then to our room. Here is the breakdown:
Room: We stayed in Room 29. It has a VERY comfortable queen bed. The room was SPOTLESS and had an amazing view of the harbor across the street. It also had a small fridge and amenities like soap, shampoo and conditioner. There is a tv but we didn’t watch it much.
There is also a nice area downstairs that offers complimentary coffee, tea, hot chocolate, granola bars, fresh fruit, ice cream, Popsicles, yogurt and pastries. VERY nice touch! No, there is no breakfast or food served there but that is NOT a big deal because of what they offer and because you are within walking distance to many restaurants.
Location: We took the ferry and left our car in Woods Hole. The area is truly walkable. We loved walking around and seeing all of the shops and restaurants (some not open for the season yet but when we come back in September, they will be).
Food: We ate at the Lookout Tavern and Linda Jeans. The food was good at both places.
We had a photo shoot to commemorate our anniversary and first time in MV. Our last shots were in the lobby of The Dockside Inn and Lianne bought out a bottle of champagne for us! So thoughtful! John also came out and wished us well. He even commented that we had an amazing sunset just as I requested (when I made the reservation).
Remembering your customers and providing such outstanding customer service is what makes this 5 stars in my book! The clean room, great location and complimentary goodies exceed well over 5 stars. I can’t say enough about this place! I can’t wait to go back and my husband feels the same way. Thank you for a fantastic anniversary!

Just got back from a 2-​night stay here for the summer solstice weekend.
I picked the Dockside based on unanimous positive feedback from my friends and Unilocal reviews. I had a great time and would return if staying in Oak Bluffs again.
The only reason for the 4-​star review is simply because of the price. I understand it’s the Vineyard and pretty much a haven for the 1%, but $ 300/​night for a tiny room gets a 1-​star deduction for value. Perhaps they used a wide angle lens taking pictures of it on the website, because it looked much bigger.
I’m not sure how the other reviewer scored a $ 99/​night room, but you’re welcome to visit their website and see for yourself (they are probably sold out for the rest of the summer anyways).
The location is unreal. You can walk to the Oak Bluffs ferry and you’re right by Nancy’s which is where you’ll wanna spend most of your day drinking and eating. There’s a café across the street for your espresso fix, and Jim’s Package Store is right there for all your libation needs. You’re a block away from Giordano’s Take Out for late night pizza and seafood. Don’t forget to go to Back Door Donuts — just follow the smell. Fresh donuts at 1am is the best thing for your waistline since the Paleo diet.
You’re also walking distance to the beach and I believe the hotel provides towels and chairs. You can also ask for a parking permit if you brought your car.
As the other reviews mentioned, there is a room with coffee and pastries in the morning, bottled water, and ice cream that is free for all guests.
The parking situation is a dirt road behind the hotel with 4 parking spaces; although with some creative parking I saw 7 cars back there including my own. I had plans in Vineyard Haven and Edgartown so I paid the $ 150 for the car ferry. I’m just not a bus/​taxi kinda guy.
The room itself was $ 259/​night, and came to $ 600 for 2 nights after taxes. It was VERY small, not much bigger than the bed itself. The bathroom was as big as the room (I think it was handicap accessible) and had a closet with mini fridge in it. The room was very clean and modern. The free WiFi was very fast.
The staff was amazing. Melissa called me the day of my arrival since I was running late just to make sure I was okay. She also gave me some tips on places to check out. I spoke to the manager, John, back in January and he was super helpful and friendly as well.
I have already recommended The Dockside to a couple of friends in real life who have since booked reservations. If you are planning on primarily staying around Oak Bluffs, you won’t need a car. I’d recommend taking the Island Queen ferry out of Falmouth as the parking situation is better than Steamship Authority.
Also, make sure you have the Google Map app on your iPhone. The GPS in my 3-​series didn’t have the towns of Oak Bluffs, Vineyard Haven, or Tisbury so I relied on my phone for most of the trip. There are a lot of confusing 1-​way streets, so study the Google Map street view if you get a free minute. Will save you from making a 9-​mile detour like I did :)

This place was fantastic! First off, rooms are super cheap for the island, starting at $ 99 for a very comfortable room. Secondly, it’s right near the Oak Bluffs Steamship Authority, so it’s a quick walk to and from the ferry. But the main thing is all the extra amenities this place includes with their room rate. You get access to their 24 hour e-​concierge via text messaging called Loomis. We used it for pretty much everything, asking from what places to eat, where to go, how to get there, etc. If it’s a really nice sunny day for you to enjoy the beach areas on the island or lay out in the sun, they have beach accessories you’re able to borrow. Also, they have an area where there are complimentary snacks, such as ice cream sandwiches/​pops, coffee/​tea, popcorn, chips, fruit, and in the morning bagels/​doughnuts. I’d recommend this place to anyone going to the island.

I recently spent one night here for my boyfriend’s birthday and we were very happy.
The Inn is located just a short walk from the ferry, which is very convenient when you have large bags. The lobby is modern and clean, and the girls checking us in were very friendly. The staff showed us around the inn which included a kitchen stocked with TONS of complementary items! Ice cream, water bottles, snacks, beer, wine etc. There were also coolers, chairs and towels for the beach and an outdoor shower and hot tub.
Our room had huge windows with an amazing view of the harbor. Right across the street are great restaurants to grab dinner and drinks with even more amazing views.
Overall a great place to spend a couple of nights on the vineyard.

My fiancé and I came to visit the island off season and stayed here, mostly because of the inexpensive rates but also due to the location. It is located right in Oaks bluff walking distance to all the stuff you want to see and right next to the ocean. Our room want an ocean view but we had access to a little deck area which was lovely for enjoying a cocktail during sunset. The room was clean and elegantly decorated. The staff was also great and recommended a yummy dinner spot and bus line tips to get to other parts if the island. There was a mini fridge in the room and ice machine around the corner. We would definatley stay here again and highly reccomend to anyone visiting MV!

Wonderful place to stay. Impressive amenities for the price. Beds were comfortable with four pillows each. Updated modern decorations. iPod/​iPhone dock beside the bed. Lots of charm and warm colors. Virtual and free text concierge. Free wifi. Countless complimentary items available all day. coffee, tea, popcorn, yogurt, fresh fruit, popsicles. I wouldn’t stay anywhere else!

Stayed here a few weeks back for a girls weekend away and overall a great experience.
I found that the staff was very friendly. They also have a room where you can go to get coffee, snacks, etc. which was great because all of the breakfast places around were mobbed. The also have a room where you can grab supplies for the beach which is really nice.
The best part was Loomis — the virtual, text based concierge. Allegedly, he is an island local and you can text him 24X7 (not sure how this is possible) for tips about the island. So, I tried this out stating that me and my girlfriends wanted to find a place for drinks on a Saturday night where we could dance and not feel like cougars. Oak Bulffs seems to be a really young crowd for nightlife. Loomis did not disappoint. He recommended the MV Chowder Company, which I would have never thought of and was just perfect with DJ, good drinks, and laid back atmosphere.
Wish we had more than a weekend there!

This was the perfect place to stay on my recent trip to Martha’s Vineyard.
I was impressed with Dockside Inn from the moment I made my reservation 6+ months ago. When I got the confirmation email there was a note in there that was written by an actual human being. It was so unexpected and awesome.
So, this place is cute as a button. (Did I just type that?) I scored a room overlooking the harbor and it was so freaking nice. I was in love with the porch — I had chairs, a table, and a bench right outside my door. One evening I was super sunburned and didn’t want to go out, so I just sat outside with a book, watched the sunset, and drank wine. Perfection doesn’t even begin to describe it. I mean… seriously. It’s what vacation dreams are made of.
Besides the perfect location, view, and porch action, they also hook you up. There is a little storage room with anything you could possibly need for the beach. Chairs? Check. Towels? Check. Umbrellas? Check. (Clearly I should have actually used an umbrella — see also: super sunburn). They even had things for collecting seashells and other random stuff. And their stuff isn’t crappy, either — my beach chair was actually really nice.
They also have this little room in the courtyard with SNACKS! Bottled water for days, a whole chest of ice cream and popsicles, popcorn, and on and on. It was a fun treat. I also noticed board games in the luggage room, so if you come with kiddos — take note.
The rooms are updated with modern décor, the bed was comfy, and there is a small fridge as well. I wish the bathroom update matched the room update — it wasn’t terrible, but they are about a decade apart décor wise. But hey, it’s a mom and pop place and everything was still fine and in working order — what more do you need? The room also had a binder full of MV tips, suggestions, and other various things. I especially liked suggestion #1. :)
The staff I encountered were all super nice. The location is perfect. I could seriously go on and on, but I was very happy with my decision to stay at the Dockside Inn and I’d stay here again without question if I ever make it back to this neck of the woods.

We came here for our honeymoon, and it will be hard to stay anywhere else after the experience here!
It is conveniently located two blocks from the Steamship Authority Ferry. When we got in, the first thing we were struck by were the signs everywhere about a water ban. It meant we couldn’t/shouldn’t drink the tap water. Apparently it happens sometimes, and affects all businesses at the same time. We didn’t know that! We thought we were staying at some dump!
The girls behind the desk were really helpful. They let us know the ban didn’t affect us anyway, since they have bottled water all the time. With the room, you get full access to their kitchen full of cold water in the fridge, ice cream, chips/​snacks, K-​cup coffee, just about anything you’ll need getting around the island. Also, you got an ice machine, ice chests (we just took one to the room to keep wine and such on ice), the jacuzzi, and outdoor shower. Let’s not forget that the girls put cookies out in the afternoon! Oh man, I know they were just regular old packaged, self-​bake cookies, but they get some good ones. Point is, this place will hook you up while staying there.
As for the room, we got a great one facing the bluff. Also had a few chairs and a coffee table outside, which I put to good use in the mornings just to hang out. Nice and clean, and air conditioned for those sticky, humid days.
Also right across the street from the package store! Made for a really relaxing stay!
We would definitely stay here again.

The Dockside is a little gem of a stay right in the heart of Oak Bluffs. You can walk to everything you could possibly want — shopping, restaurants, the beach, and the attention to detail within the Inn itself makes it absolutely charming. The rooms are clean and spacious, the décor is fun and modern, there is a lovely garden with jacuzzi in the back, and an enclosed coffee/​snack area (with incredibly addicting cookies) that you can help yourself to. Not to mention the staff, who were incredibly friendly. I arrived late in the afternoon by myself and wanted to get a pedicure, which Kathy was so helpful to arrange and even let me borrow her car to drive the 3 miles to. (The closer salons were already booked given the time of day.) After the front desk closes, or any time, they have a virtual concierge, Loomis, which you can text for things like where to find a late night spot to get something to eat. It was a short, but fantastic stay and I’m looking forward to my next visit down — I highly recommend it any time you’re staying on the Vineyard!

Very happy I chose to stay at Dockside Inn during my last visit to Martha’s Vineyard. My room was spotless, the bed was very comfortable with nice linens, the shower had excellent pressure (which is a huge plus in my book), and I appreciated the light blocking blinds on the windows. The staff was very friendly and helpful, and the free coffee bar is a great idea. I will definitely stay at the Dockside Inn again!

We were pretty disappointed by the Dockside after seeing so many positive Unilocal and Tripadvisor reviews. Their website also does a good job deceiving you into thinking this is an upscale place. However, it looks like an old motel that got a fresh coat of paint and some new carpets.
Our room smelled a bit musty, the TV was tiny, and there was no phone in the room. The biggest problem with the room was that our heating/​AC unit smelled like a skunk. When I told the girl at the front desk about this I was told «Well, we do have skunks on the island.» … Great, now what are you going to do about it? It was like pulling teeth to get her to try to resolve the issue. A maintenance person did come out shortly thereafter and mostly solved the issue, but I couldn’t believe the reaction of the girl on duty. To be fair, afterwards, she did leave a nice bottle of wine in our room apologizing.
We were pretty psyched about their hot tub, but found it was pretty small and also the cover smelled very moldy.
Also, their front desk closes at 10pm and the only method of contact after that is a text-​message based concierge system. Ridiculous.
One very important thing to note is that they do not have guaranteed parking, though their website leads you to believe they might. They only 6 or so parking spots for about 30 rooms. We had paid to take our car over on the ferry and when we found this out were pretty upset since if we wanted to keep our parking spot we basically couldn’t take the car around much. There is overnight offstreet parking nearby, but you have to move your car by 8am. Lame.
We’ll be trying somewhere else next time.

Super clean
Convenient location
Unbelievably friendly staff
We loved Loomis, the virtual concierge.
We stayed in room 20 — it had an extra set of windows overlooking the harbor. Even though this is very close to the main strip, the streets were very quiet. It was amazing to be able to sleep with the windows open (a luxury we rarely get, living in NYC)!
Overall, I would definitely recommend this place to others.

If you are not a BALLER and have a house already… this is a great alternative.
I booked because I read reviews on Unilocal,Trip Advisor, etc. I figured out before i got there that they had just renovated the place.
I am pretty sure we were in the first 10 people that have stayed in our room. The rooms are very well decorated, VERY clean, and perfect amount of space. The renovations really make this place TOP NOTCH.
There is FREE WiFi, and they let you borrow towels, umbrellas, and beach chairs. How cool is that???
They do not have a pool — but they have a hot tub. They also have a cool service where you can text a number where someone will answer your questions — it’s a virtual concierge. It’s not a computer, but a real person.
Great location — easy to walk to Oak Bluffs and from the Ferry.

Nice but overpriced. We stayed for 4 days in early August. The price was $ 300/​rm. We stayed here b/​c they allowed dogs. Good location. The rooms were tidy but not worth $ 300. Breakfast was also disappointing (Stale bagels from Costco). They do had a nice hot tub. We did have a problem with the bill which was irritating too.
Overall, not worth the money.
It’s of other nicer hotels in town.

This is THE hotel to stay in when you are itching to get to the Vineyard.
Close to everything. It’s itn the heart of Oak Bluffs. You can walk all over town. Just go!