Martha’s Vineyard Accommodations

August is the most popular month for travel to Martha’s Vineyard; the weather is typically superb and the island is bursting with activity and special events!

All this excitement means that finding a place to stay on the island can sometimes pose challenges. Some hotels have already started booking rooms for next August and most will likely be fully booked before the end of the year. To make things slightly more difficult, most of the popular hotels will not allow us to block rooms, which means we cannot guarantee a reserved hotel room for our guests.

The best solution is for everyone to book their accommodations in advance. To help, we’ve taken the time to not only research but we’ve even visited many of the hotels around the island. Listed below you will find links to places we recommend. And, if you book soon, you will also get the best possible deal on a room. We strongly recommend that you book your room as soon as possible.

The good news is that there are tons of options for accommodations across the island, from affordable hotels to high-end inns and B&Bs, plus weekly rental houses, condos, and beachside bungalows. We can’t possibly include them all here but you should consider taking the time to search online for other options. Please feel free to contact us anytime if you have questions.

Lastly, when you do have your accommodations booked, please take the time to shoot us an email, so that we can keep track of who is staying where and who still needs help finding the perfect place to stay. This will also help us arrange welcome gifts for our guests and transportation around the island.

Accommodations in Oak Bluffs  –  within walking distance of the wedding venue
I highly recommend these first 3 locations.  They are affiliated with each other and are some of the most affordable options right in the middle of everything!  Also, the owner is sweet and helpful, which is really valuable!

  • Madison Inn  –  This Inn comes highly recommended by a close family friend. It is located in downtown OB, minutes away from the ferry docks and the wedding venue! We have been in touch with Mary, the owner, and she encourages booking in the next couple of months. Most of her rooms fill up by winter.
  • Nashua House  –  The Nashua House is also owned by Mary and her husband and is a great option if you’d like a lower-priced room.  These rooms have shared bathrooms, so it’s an excellent option for groups who know each other (or want to get to know each other).
  • The Dockside Inn  –  This Inn is also affiliated with the Madison and Nashua House. It’s located right on the Oak Bluffs Harbor, offering great views!
  • The Wesley Hotel  – The Wesley is one of the only large hotels on the island. It faces the Oak Bluffs Harbor, with beautiful ocean views, and it’s in a great location for beach access, restaurants, and more. We’ve been in touch with them and they have limited availability for next August. They do not begin booking rooms until November. If you check out their site and absolutely love it, you could try for a room, but I would recommend one of the other three listed above.
  • Capricorn House  – This is a small rooming house right on the beach. It could be a fun option, if you’d like to spend a lot of time on the beach.

Accommodations in Oak Bluffs  –  not within in walking distance of wedding venue
If you’re interested in staying tucked away from the tourist hustle-and-bustle but close enough to the wedding venues, then there’s one little gem that might be ideal for you.

  • Island Inn  –  The Island Inn is located a short drive / bike ride from downtown Oak Bluffs. There is a bus stop right outside of the hotel, so transportation is easy! It’s right next door to Farm Neck Golf Club, where you might catch a glimpse of President Obama working on his game. It is also home to Lola’s, one of my favorite restaurants in Oak Bluffs, possibly on the entire island! 

Accommodations outside of Oak Bluffs
While Oak Bluffs is the most convenient place to stay for the wedding, it is only one of six towns on Martha’s Vineyard. If you are hoping to turn the wedding weekend into an excuse for an extended vacation (smart move you!), then you may want to consider broadening your search for accommodations. Vineyard Haven is the closest town to Oak Bluffs but Edgartown is an excellent option as well. Public transportation is a very convenient way to get around the island or you could consider renting bikes to get around. Chillmark, Menemsha, and Aquinnah are on the opposite side of the island; they offer some of the best sunsets around but, if you are interest in staying up-island, we’d advise looking into a rental vehicle to get around.

  • Kelley House (Edgartown)  –  located in downtown Edgartown, this is a great option if you don’t mind traveling back-and-forth to wedding events. There are lots of rooms available, plus it’s a great town for shopping, restaurants, etc.
  • Edgartown is also home to a lot of boutique inns and quaint B&Bs. It’s worth poking around online, if you have something specific in mind.
  • Vineyard Harbor Motel (Vineyard Haven)  –  This is an affordable option in Vineyard Haven with views of the Vineyard Haven Harbor. It’s a short drive from Oak Bluffs and all the wedding locations. 

Rental Houses
If you plan on staying longer than the weekend, a vacation rental might be the best for you. Keep in mind that many rental homes are available Saturday – Saturday, so if you’d like to get into town the day before the wedding and stay for an extended vacation, then we can guarantee you some fun. The week following the wedding is Cara’s favorite week on the island  –  Grand Illumination, Fireworks, and the Agricultural Fair are a few of the week’s annual events. These events also happen to coincide with the President’s annual family vacation, plus you may run into a few celebrities along the way. However, since it’s such a busy week on the island, prices tend to bump up. You could consider renting a house with friends or family to make it more cost effective than a hotel. Also, if you are interested in the house idea, please let us know. We might be able to pair you up with other wedding guests interested in sharing a house to further reduce expenses.

Here are some vacation rental websites worth looking into:

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