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Rental Documents

Check In & Check Out

Your home will be clean and ready by 4 p.m. In the event that it is ready early, we will text you on the day of your arrival. If you are arriving early to the Island we can arrange for you to drop your luggage off at our office located at 2 Wing Road, Oak Bluffs, MA 02557.

Upon check-in if there are any cleaning or damage issues at the house, please inform us within 2 hours of your arrival.

Repairs & Maintenance

Please contact the caretaker or Grace Hagerty Real Estate if an appliance, plumbing, heating or cooling system fails to function properly. We will make every effort to have them responded to as soon as possible.


If you would like additional cleaning during your stay, please let us know.

Trash Removal

Trash is picked up on certain days. All garbage must be bagged for pick up. Please inquire with your rental agent for details.

Checking Out

By 10 a.m. on the day of your departure, your vacation home needs to be empty of all of your belongings. All trash must be bagged and placed in the trash bins. Please dispose of all food and drinks. Only unopened beverages may be left behind.

Rental Terms and Policies

Renting a Vacation Home

After reviewing the rental listings, please contact us to discuss and book the home that best suits your needs. The agent will confirm the price and availability. A lease will be prepared and sent by email or mail for signatures.

Vacation Rental Taxes

As of January 1, 2019, short-term rental stays of 31 consecutive days or less are now subject to a state room occupancy tax. The tax rates are as follows:


Town 4% + State 5.7% = 9.7%


Town 4% + State 5.7% = 9.7%


Town 4% + State 5.7% = 9.7%

Oak Bluffs

Town 6% + State 5.7% = 11.7%


Town 6% + State 5.7% = 11.7%

West Tisbury

Town 6% + State 5.7% = 11.7%

These taxes are paid by the renter at the time of booking.

There are only two exemptions to this tax:

- If the lease period is for over 31 consecutive days.

- If the property is rented for only 14 days a year or less; Owner must file a declaration.


The Contract

We will send you a copy of the lease, which is due back with your signature and a 50% deposit of the total rental amount within seven days. If we do not receive the leases and payment, the homeowner has the right to rent to another tenant. The final payment and security deposit will be due 30 days before your arrival date. 

Security Deposit

The typical security deposit is 10% of the total rental amount. This amount could be more at certain properties. The deposit is held by us and returned to you within 60 days from your departure date. Deductions from your security deposit include the post-departure cleaning fee, cost to repair any damages, and any long distance phone calls or pay per view cable TV purchases.

Canceling Your Lease

If it becomes necessary to cancel your rental, it is required that you notify us as soon as possible. We will do our best to re-rent the property. If we are able to re-rent it, we will return your money, less a 15% cancellation fee. Otherwise, you are responsible for the payment in full as stated in the lease.


Check in time is 4 p.m. and check out time is 10 a.m. Our homes are non-smoking. Pets are sometimes allowed. They must be pre-approved and a pet deposit will be required. All of our vacation homes are offered furnished with all bed/bath linens, cooking, and dining utensils.

Getting to Martha's Vineyard

Martha’s Vineyard really is an Island — there are no tunnels or bridges connecting the Vineyard to the mainland, so there are two ways to travel to the island: take a ferry or fly!


Taking the Ferry to Martha’s Vineyard  

There are lots of ferry options between May - October. The only ferry service that can carry cars, motorcycles, and trucks is the Steamship Authority.

Steamship Authority: Woods Hole to Martha’s Vineyard

If you plan on bringing your vehicle to the Island, you MUST make a reservation in advance. Please visit their website or call their reservation & information number at (508) 477-8600 to view the schedule, make a reservation for your vehicle, or ask any questions. The Steamship Authority is open year-round!

Hy-Line Cruises: Hyannis/Nantucket to Martha’s Vineyard

Hyannis Ferry 2021 Opening Day: May 1st

Nantucket Ferry 2021 Opening Day: May 28th

Seastreak: New Bedford/New Jersey/New York City to Martha’s Vineyard

New Bedford Ferry 2021 Opening Day: May 5th

New Jersey / New York Ferry 2021 Opening Day: June 28th

Island Queen: Falmouth to Martha’s Vineyard

2021 Opening Day: May 28th

Vineyard Fast Ferry: Rhode Island to Martha’s Vineyard

2021 Opening Day: May 28th


Flying to Martha’s Vineyard

If you do not need to bring your own vehicle to the island, flying is a great option

Cape Air

Offers daily, year-round flights from Boston. They also have additional seasonal service from New Bedford, Hyannis, and Nantucket in Massachusetts, and Penn Station and Westchester in New York.


Provides seasonal flights from Boston’s Logan Airport and New York’s JFK Airport direct to Martha’s Vineyard.