Renting on Martha's Vineyard

Deciding to rent a home on Martha’s Vineyard is one of the best decisions you can make for creating a memorable family vacation. Not only will it create lasting memories, but you will come away having made friends for life with those you have met during your stay.

However, early planning is key to making the vision come true and avoiding disappointments. Many people, once they have found their ideal rental, make a point of returning every year and thus secure the next year’s rental at the end of their current stay. Thus, it’s never too early to inquire about a property.

Next, reservations for getting to the island, whether by air or ferry, should be made as soon as you know the dates of your stay. Always inquire if ferry reservations come with the rental. Many agencies and homes provide ferry tickets which you will come to appreciate as an important benefit.

Getting To Martha's Vineyard By Ferry

Headstart 2023: January 10 to 16, 2023

The earliest summer reservations may be made through the Headstart program. To become a member of the Headstart program, begin by accessing the 2023 Headstart Reservation Application here.

The 2023 Headstart opening will begin on Tuesday, January 10, 2023 starting at 7:30 a.m. EST.

On Tuesday, January 10, 2023, Headstart customers (who must be in the Excursion and/or Preferred programs to participate) may make reservations for travel from May 18, 2023 through October 23, 2023 online and via U.S. mail.

Qualified island residents who are current participants in either the 2023 Excursion or Preferred program are eligible to participate in the 2023 Headstart Program.

Each pre-qualified island resident will be allowed to make up to five one-way or round-trip reservations between the dates of May 18, 2023 and October 23, 2023. Of those five, three may be made as transferable reservations.

2023 Martha's Vineyard General Public Internet Opening: January 24 to January 30, 2023

For Martha’s Vineyard Travel ONLY

2023 Summer Reservations (May 18, 2023 through October 23, 2023) can be made online starting on January 24, 2023 at 5:00 a.m. EST.  Reservations submitted via postal mail (up to five one-way or round-trip reservations will be accepted per mailing) will be processed as received beginning January 24, 2023.

The Reservation Office will have extended hours to provide additional support to customers January 24 to 30 from 5:00 a.m. to 6:00 p.m. EST.

2023 Summer Reservations - Telephone, Internet and Mail Opening: January 31, 2023

2023 Summer reservations for the time period of May 18, 2023 through October 23, 2023 may be made via online, phone, or postal mail starting January 31, 2023 at 7:30 a.m. EST.

Up to five transactions (one-way or round-trip) will be accepted per telephone call or via postal mail.

Getting Around Martha’s Vineyard

You can get around the island via car, bike, electric bike or bus (Martha’s Vineyard Transportation Authority). If you plan on using the bus, get a pass, which are available for 31 days, 100 days and 365 Days. If you don’t have a bike or car, there are rentals available at locations near the ferry terminals in Vineyard Haven and Oak Bluffs.

Maps of the island are available in free Vineyard guides which you can find on the ferry and in various island stores.

Sometimes people get confused when they read what looks like Upisland. Up-island refers to the three up-island towns, Aquinnah, Chilmark and West Tisbury. Down-island towns are Vineyard Haven, Oak Bluffs and Edgartown.

And, if you are not sure where you are, ask someone. Vineyard people are always glad to help.

Our Sample Rentals

Vineyard Haven, Tashmoo Wood Condo

Enjoy the private community of Tashmoo Wood in this elegant end-unit condo that features views towards the No. 7 hole of the adjacent Mink Meadows golf course. Usually available only in June.

2 bedrooms

3 bathrooms

Sleeps 4-6 Adults

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West Tisbury, Tiasquam Road Home

A rustic retreat in a pristine setting in bucolic West Tisbury. When you get to the end of the dirt road, you won't want to leave... except to go to the beach.

4 bedrooms

5 bathrooms

Sleeps 8 Adults

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Oak Bluffs, Beth Way Retreat

Escape to your own magical hideway in Oak Bluffs, while being close to championship golf at Farm Neck Golf Club, and a quick drive to the down-island towns of Edgartown & Vineyard Haven. Features a swimming pool, fire pit, bluestone terrace and guest house.

4 bedrooms

5 bathrooms

Sleeps 8 Adults

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Martha's Vineyard Real Estate Properties By Town

Martha's Vineyard Real Estate Properties By Type