Cheapest option by far: Camp on the Ryerson's lawn! It's plenty big enough for lots of tents and Admiral Benbow's Inn is just steps away! There's an outdoor shower and an indoor bathroom as well if Admiral Benbow is too crude for your tastes. Plus there's always the lake to bathe in:) Max and I will be staying in the boathouse, so we'd love to have you close by (though we may try to put you to work chopping vegetables).
Attleboro House, Oak Bluffs
508-693-4346 (leave a message and they will call you back)
$105
shared bathrooms
The Farmhouse B&B, North Tisbury
www.mvfarmhouse.com
$110-$165
The Red Hat B&B, West Tisbury
www.theredhat.com
$115 with shared bath
Duck Inn, Aquinnah
www.gayheadrealty.com/DuckInnofMarthasVineyard.html
$115-$195
hot tub
Pet Friendly!
The Bayberry Inn, West Tisbury
mvbayberry.vineyard.net
shared bath $125, private bath $190
The Tivoli Inn, Oak Bluffs
www.tivoliinn.com
shared bath $125-$155, private bath $165-$235
Narragansett House, Oak Bluffs
www.narragansetthouse.com
$125-$275
The Nashua House Hotel, Oak Bluffs
www.nashuahouse.com
$119 for a single, $139-$149 for doubles, all shared baths
Menemsha Inn & Cottages, Menemsha
www.menemshainn.com
$145-$190
Clark House Inn, Vineyard Haven
www.clarkhouseinn.com
$150-$235
Arend’s Samoset-on-the-Sound, Oak Bluffs
www.samosetinn.com
$155-$195
some rooms have shared baths
Marni’s House, Vineyard Haven
www.marnishouse.com
$175-$200
one room allows pets
Admiral Benbow Inn, Oak Bluffs
www.admiral-benbow-inn.com
$185-$215
one room sleeps 4 adults
Hanover House Inn, Vineyard Haven
www.hanoverhouseinn.com
$185-$235
Dockside Inn, Oak Bluffs
www.vineyardinns.com/dockside.html
$185-$235
The Beach House on the Ocean, Oak Bluffs
www.beachhousemv.com
$190-$205
rollaway bed to accommodate 3rd person in room for $20 extra
Island Inn, Oak Bluffs
www.islandinn.com
2 adults $200-$235, 4 adults $275-$385
pool, tennis and golf
Pet Friendly!
Lambert’s Cove Inn, West Tisbury
www.lambertscoveinn.com
$220-$350
restaurant, pool, spa and tennis on site
The Inn at Blueberry Hill, Chilmark
www.blueberryinn.com
$262-$318
lap pool, spa and restaurant on site
Beach Plum Inn, Menemsha
www.beachpluminn.com/theinn.htm
$275-$400
Lots more B&Bs are listed on this page:
http://www.sunsol.com/ccvd/lodging/mthvinbb.html
Many of them close down in the winter and won’t take reservations until spring, or at least until January. It's hard to reach anyone in the off-season even to check rates (I tried), but if you leave messages, some of them will call you back. I assume their response times will improve in the spring and summer.