FAQ rent vacation homes

I’ve never been to the vineyard. Where would you suggest we rent?

Martha’s Vineyard is diverse and consists of six town. Vineyard Haven, Edgartown, and Oak Bluffs are our “down-island” towns and have more shopping, restaurants, and activities. Chilmark, West Tisbury, and Aquinnah are our “up-island” towns and are more rural and laid back.

Depending on the ages in your group and your general lifestyle, you may opt for one town over the other. You can read more details about each town on the Our Island section of this site.

What is the best time to rent on the island, and how soon do I need to book a rental?

Peak season is July and August and is most popular because the weather is the warmest and the island is bustling with numerous things to do. The shoulder season is June and September appeals to those looking for a quieter vacation. The ideal time to book your rental home is from November to March, the sooner, the better.

Can you tell me what the house is like, does it have a yard, are the rooms big, can you show me pictures of the inside and the views out the window of the master bedroom or the living room?

Our rental agents are well-versed in all our rental properties and can describe the floor plan and provide photos as well. In the off chance that we haven’t seen the property, we can certainly preview it for you. Our rental listing are viewable on the Featured Rentals section of this site.

How do we get directions and the key to the house?

The week prior your rental agent will coordinate the details of your arrival with you.

What kind of activities are there for us to do, are there any activities for children, what about for teens?

The island provides many activities for young children, teens, and adults such as watersports, fishing, boating, bicycling, hiking, horseback riding, tennis, and golf. There are also specific activities geared towards children like the Flying Horses Carousel, the Felix Neck Wildlife Sanctuary, Featherstone Center for the Arts, and the YMCA to name a few. You can visit the Calendar of Events section of this site for specific events.

If there is a problem at the house, who do I call?

Your first call should be to the rental agent who booked your rental home. They in turn will contact the homeowner and necessary persons to address the issue.

Do I need a car? If so can I rent one and how far in advance do I have to reserve one?

Most tenants prefer to bring their own vehicle for convenience. If it is not convenient, there are several car rental agencies on the island. You should reserve your vehicle as soon as you book your rental home.

There is also an extensive bus transportation system call the Vineyard Transit Authority (VTA) that can take you to all areas of the island.

I want to bring my car, how and when do I get ferry tickets?

As soon as you have locked in a rental home, you should go to Steamship Authority website  and book your ferry reservation. You can also book your reservation by phone.

Is this summer rental dog friendly?

Some home owners allow pets but most do not. If you want to bring your pet, it is important to provide that information to your rental agent prior to booking a rental home.

Where can I shop for food, wine, etc.?

All alcoholic beverages can be bought at liquors stores located in Edgartown and Oak Bluffs. For food there are five supermarkets and several convenience stores located around the island.

Can I get a cleaner, babysitter, childcare… during my stay?

Your rental can recommend good cleaners, sitters, and other service providers.

Should I bring a crib, bicycle etc or can I rent these locally?

You can bring your own bikes and cribs but it is not necessary as you can readily rent these locally.

Does the house have high-speed internet? Is it wireless?

Most homeowners are up to date with internet technology. However, you should ask your rental agent to confirm these details prior to you booking your rental home.

What will the owner provide for tenants; sheets, towels, beach towels and beach chairs…? Is there a place to keep our bikes?

Some homeowner provide bed and bath linens and some do not. Typically beach towels and beach chairs are not provided. There are options to rent these items locally and your agent can provide you with the contact information. Rule of thumb is to ask your rental agent to confirm these details prior to booking your rental home.

What kinds of entertainment equipment does the house have; TV, DVD or CD player, radio?

These items are listed online in the detail page of the rental listing. Specifics about these items can be confirmed with your listing agent.

What do I need to do when we are leaving the house at the end of our vacation?

Typically tenants should leave the house in the same general tidy condition in which it was found. All food, trash, and recyclables should be removed and put in the provided receptacles. You should always refer to your lease for specific instructions upon your departure.

What do we do with the key when we are leaving? Do we leave the house open or locked?

Upon departure, tenants should lock all windows and doors, and the key left as coordinated with your rental agent.