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So, you’re planning a Vineyard vacation. Congratulations! In this section of our site, we’ve worked to compile the basic information you should know if you’re considering coming to Martha’s Vineyard and would like to rent a furnished home to live in during your stay.

Every summer, tens of thousands of people come to the Vineyard to enjoy our beautiful beaches and the quaint country charm typified by flower and produce stands that operate on the honor system. Many visitors feel that coming to the Vineyard is like stepping back in time, to when things moved more slowly, people trusted each other, and the simple things in life — a walk through the woods, eating watermelon on a porch, stargazing, or a leisurely bike ride with family and friends — was what mattered most. Sure, we’ve got great restaurants, shops, and lots of activities for young and old alike, but getting away from the hustle and bustle is what most Vineyard visitors crave.

The following links will guide you through the information in this area of our site. As always, if you need assistance, please do not hesitate to contact us.
What to expect when you’re renting

Information on how to use our rental property database, save search results, and e-mail them to friends

Booking your vacation rental

Information for first-time visitors

Information for off-season rentals

Year-round rentals


See Our Featured Properties for Rent



What to expect when you’re renting


Rental properties on Martha’s Vineyard vary from the most simple summer cottage to beautiful secluded mansions many can only dream of renting. As a rule, most properties are available on a weekly or bi-weekly basis, with most of the “nicer” properties requiring a two-week or longer stay. Prices range from roughly $1,000 per week to well over $25,000 per week in season. High season is generally July and August. Shoulder-season bookings in April, May, June, September, and October are also available, generally at reduced prices. Some properties are also available during the holidays and off-season.

Aquinnah, Chilmark, and West Tisbury are more secluded and tend to be the more expensive towns. Oak Bluffs has the most mid- to low-end listings and is best suited for those looking for a busy, younger environment. Edgartown and Vineyard Haven both offer a good selection of mid- and high-end properties, some waterfront or water views, with easy access to town amenities.

Booking early is highly advisable. Many of the island’s summer visitors return every year, so properties begin to book as early as a full year in advance. By Christmas, July and August inventories begin to thin, and by March or April, you may need to be flexible in both the location of your booking and the weeks of your visit. But don’t despair if you can’t find what you want! Our rental agents will work with you to help you find a great Martha’s Vineyard vacation rental.

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How to use our rental property database, save search results, and e-mail them to friends


To find an available rental property that suits your needs, you can either use the Search Properties function in the left-hand column for a Quick Search or click here for a Detailed Search. Be sure to click on the For Rent button to see rentals. You can select one or more towns by pressing and holding the Ctrl key (Command key on a Mac) and clicking on the towns you want to select. Or choose All to find a property that meets your search criteria in any town. You can also browse the entire database and sort by price, location, and number of bedrooms to get a better understanding of what’s available in different areas and price ranges.

It’s a good idea to rank your needs and preferences before you conduct your search and to remember that some items will work against each other. For example, if you’re looking for a low price, you probably won’t be finding waterfront properties! Talk over priorities with others who may be sharing the house with you, and get a consensus on what is most important for the group as you begin to search. Try to prioritize the items on the following list to help clarify your group’s wants vs. needs.

• Weekly price

• Time of visit (weeks available)

• Location: secluded, in-town, waterfront, beach access, etc.

• Number of bedrooms/other sleeping arrangements

• Property type: single family, guest house, multi-family, etc

• Town preference (Chilmark, Edgartown, Oak Bluffs, etc.)

• Special requirements: pets allowed, smoking permitted, washer/dryer, linens provided, etc.

Once you have an idea of where you’re willing to compromise, begin the search process. In the detailed search area, you can specify all required items and look through the results. You can also save your search criteria and save and e-mail search results to others by becoming a registered user. Once you have saved your search criteria and results, you can modify the information, add new properties to the results, and work with a Coldwell Banker Landmarks rental agent to find more properties.

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Booking your vacation rental

If you’ve successfully found a property you are interested in renting, and it looks to be available when you want, you’re ready to book! To confirm your rental, you need to work with a Coldwell Banker Landmarks rental agent, who will generate a lease for you, collect the necessary deposits, and review the rental terms and conditions with you.

You can either call us at (508) 693-6866 Monday-Saturday from 9:00 am to 5:30 pm eastern time, or click here to send an e-mail, and we will contact you. Please include your name, e-mail, and registered Coldwell Banker Landmarks username so that we can access your search results and confirm availability of the property you’re interested in.

Please note, most rental properties on the island are listed by multiple agencies, and unless the property owners keep their availability records up to date, the availability information shown in our database may not be 100% accurate.

If the property you are interested in is not available on the dates you have selected, be assured that your Coldwell Banker Landmarks rental agent will work diligently to find you a comparable property in a timely fashion.

If you have not been able to find a property to meet your criteria, or you prefer to have a Coldwell Banker Landmarks rental agent conduct a rental search for you, please do not hesitate to contact us! We’re happy to help.

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Information for first-time visitors

If you’re coming to the Vineyard for the first time, be sure to read through the information entitled The Island. If you’re planning to bring a car, you should contact the Steamship Authority advanced auto reservations bureau (508) 477-8600 as soon as possible to coordinate arrival and departure dates. Visit www.steamshipauthority.com for more information on bringing a car to the Vineyard.

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Information for off-season rentals


Many rental properties are available during the off-season, the time of year most locals prefer! The holiday season is active in most areas of the island, and many seasonal homeowners enjoy lovely holiday breaks with their families and friends here. If you are interested in an off-season rental, please contact a Coldwell Banker Landmarks rental agent, and we will help you with the special requirements of off-season rentals.

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Year-round rentals

Due to the abundant seasonal rental market on Martha’s Vineyard, year-round rentals tend to be difficult to find. However, given our many local resources and contacts with landlords, we may be able to assist you locating a suitable year-round rental property. Please contact a Coldwell Banker Landmarks rental agent, and we will work to assist you.

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Marthas Vineyard Rentals, Martha's Vineyard Rental, Martha's Vineyard, Martha's Vineyard rentals, Marthas Vineyard, Martha's Vineyard luxury rentals, Marthas Vineyard summer rental, Coldwell Banker Rentals, Coldwell Banker Landmarks Rentals Vineyard Haven Single family home Waterfront
Wonderful, sprawling summer house overlooking Vineyard Haven Sound. The spacious and comfortable interior and lovely gardens and lawn sweeping down to a private ocean beach are reminiscent of a bygone era. Wonderful glassed-in veranda and complete privacy.
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Marthas Vineyard Rentals, Martha's Vineyard Rental, Martha's Vineyard, Martha's Vineyard rentals, Marthas Vineyard, Martha's Vineyard luxury rentals, Marthas Vineyard summer rental, Coldwell Banker Rentals, Coldwell Banker Landmarks Rentals Oak Bluffs Single family home Waterfront
Waterfront vineyard-style cottage with exposed beams. Very charming, with fantastic views of the Vineyard Sound and Lagoon. Stairs in front of home lead directly to a nice, sandy beach. On the Lagoon with easy access to swimming, boating and kayaking. Close to downtown Oak Bluffs and Vineyard Haven. A tranquil retreat yet convenient to downtown activities.
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Marthas Vineyard Rentals, Martha's Vineyard Rental, Martha's Vineyard, Martha's Vineyard rentals, Marthas Vineyard, Martha's Vineyard luxury rentals, Marthas Vineyard summer rental, Coldwell Banker Rentals, Coldwell Banker Landmarks Rentals West Tisbury Single family home Waterfront
Highly sought after Lambert's Cove Road waterfront location with a fabulous, private North Shore beach. Bright and airy interior with incredible views toward Woods Hole. Equipped with beach chairs and umbrellas for the beach.
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Marthas Vineyard Rentals, Martha's Vineyard Rental, Martha's Vineyard, Martha's Vineyard rentals, Marthas Vineyard, Martha's Vineyard luxury rentals, Marthas Vineyard summer rental, Coldwell Banker Rentals, Coldwell Banker Landmarks Rentals Oak Bluffs Single family home Waterfront
This is life at the water's edge. This is life in a classic old-fashioned Vineyard summer cottage, spacious and simple. Nothing fancy, yet everything comfortable. If you want to wake up every morning of your vacation faced with the awe-inspiring beauty of a fascinating waterfront location, then this is it. Go to sleep hearing the waves, watch the ferries during the day, savor sunsets every night over the water. Swim whenever you like. Life moves easily from indoors to outdoors. Enjoy all your meals outside on the terrace. It's a summer's enchantment.
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Marthas Vineyard Rentals, Martha's Vineyard Rental, Martha's Vineyard, Martha's Vineyard rentals, Marthas Vineyard, Martha's Vineyard luxury rentals, Marthas Vineyard summer rental, Coldwell Banker Rentals, Coldwell Banker Landmarks Rentals Vineyard Haven Single family home Water view
Traditional style Vineyard home, wonderfully renovated for contemporary living. Offers nice waterview of Vineyard Haven harbor. Great location to town, ferry and shops. Wide-screen plasma TV on third floor family room.
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Marthas Vineyard Rentals, Martha's Vineyard Rental, Martha's Vineyard, Martha's Vineyard rentals, Marthas Vineyard, Martha's Vineyard luxury rentals, Marthas Vineyard summer rental, Coldwell Banker Rentals, Coldwell Banker Landmarks Rentals Vineyard Haven Single family home Waterfront
Classic beach house with large wraparound deck, spacious interior, elegantly casual. Detached one bedroom, one bath bunk house. Long stretch of sandy beach.
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Coldwell Banker Landmarks Real Estate
Vineyard Haven Office
15 Church Street
P.O. Box 817
Vineyard Haven, MA 02568
(508) 693-6866

Oak Bluffs Office
90 Dukes County Avenue
Oak Bluffs, MA 02557
(508) 696-8266

Landmarks@mvLandmarks.com

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