There's really only 3 decent size towns on Matha's Vineyard that have a variety of shops/restaurants and nearby beaches:

Edgartown
Oak Bluffs
Vneyard Haven

We stayed in Edgartown and really liked it - plenty of B&B's and small hotels all within a few blocks of the town.

I've stayed in Oak Bluffs and enjoyed doing so.

If memory serves, there are more ferries that come into Vineyard Haven and Oak Bluffs than Edgartown. Note also that there are more tourist attractions in Edgartown and Oak Bluffs than Vineyard Haven. Note also (if it matters to you) that Oak Bluffs and Edgartown are the only towns that are not "dry" on the island. Shopping options seemed about the same in all three. My impression also was that there are more public beaches near Oak Bluffs than the other two towns.

The ferries only come into Oak Bluffs and Vineyard Haven. And you are more likely to find economical accomodations there...there are some nice b&b's on the water in Oak Bluffs.

But personally, I like Edgartown the best. There are loads of nice b&b's right in town, and you can get the shuttle to South Beach (also called Katama) which is one of the nicest beaches on the island. You can also bike to East Beach, using the On Time Ferry to go across to Chappaquidick.

The other towns, West Tisbury, Aquinnah, Chillmark, Menemsha, are all very nice, but quite expensive, and much more difficult to stay in if you don't have a car. Plus there are fewer inns, and beaches hard to access (they are still public beaches, but the parking is private and there are no shuttles. They make it tough for you to go there).

Do you plan to try to take a car across? It can be extremely difficult to get car reservations on the ferry. I suspect you need to have done it already for a weekend in August

FYI - parking (especially in summer months) is sometimes very difficult in the three main towns. It's often very limited and "metered" so you have to keep putting coins in the meters or risk getting a ticket or your car towed.

If memory serves, there is a seasonal ferry that runs between Edgartown and Falmouth (not Woods Hole, either). But indeed, most of the ferries go to Vineyard Haven or Oak Bluffs.

I like Edgartown the best, much better than Oak Bluffs.

Bachs is correct about the Edgartown ferry from Falmouth--not sure of the particulars, it is a much smaller boat but goes directly there--you could Google.

Thanks so much for the responses. It sounds like Edgartown might be the best choice. Does anyone have any great inn/B&B recommendations?

we stayed at the charlotte inn in Edgartown - veery, very nice B&B but it's a bit more than $300/night for their least expensive room.

You can find a list of just about every B&B in Edgartown (all with plenty of reviews) on TripAdvisor - http://www.tripadvisor.com/Hotels-g41558-Edgartown_Martha_s_Vineyard_Massachusetts-Hotels.html)

Sorry, I can't help with lodging but there's also a seasonal ferry from New Bedford, MA. I've taken it before and it's a nice ferry ride. One hour.

http://www.seastreak.com/default.aspx

I don't know the names of them but Edgartown has some lovely B&Bs on the side streets just outside of downtown. They are throwbacks to another time. Let me see if I can figure out which streets....NOW full disclosure! I have only seen these places from their gardens and lobbies. I have not stayed in them.

OK, this is one of the ones we have been totally charmed by from the outside. On a lovely little street. However you would need to find other info about what it is like to stay in. I did not check the prices....

http://www.charlotteinn.net/brochure.htm

DOH! Just noticed it is the same one that was mentioned above!

As I mentioned, we stayed at the Charlotte Inn - a terrific place but it probably will exceed OP's $300/night budget. They rooms a very well appointed, the gardens are lovely, the staff was very friendly and accommodating and the home itself is impeccably maintained. Best of all you can walk to just about everything in Edgartown.

I was wondering, RA, when we have stayed in B&Bs on the Cape, they have been really noisy, as they generally are just old houses w/o soundproofing of any kind...what did you notice at this place? I know that some are not so sensitive, but it is my main issue with any overnight accommodations.