When Should You Book Your Vineyard Vacation?

Pool with view of Sengekontacket PondOn Martha’s Vineyard, we begin booking rental homes for the following season before the current one ends!  Many families decide they like coming to the island every year for a least one week.  If they like the rental property they are staying in, and know they will be back, it makes sense for them to commit to the same house while they are here.

Vineyard Haven Beach Frontage

Rental home bookings continue through the fall and right up until the beginning of the season.  Critical things to consider when trying to decide when to book your vacation home:

  • Most owners know whether their repeat tenants are coming back by the end of September.  If you are a new tenant or looking to change houses it may be difficult to get a commitment prior to that.
  • Steamship Authority (vehicle ferry) opens up ticket sales for the summer months around mid January.  Tickets sell out quickly for the weekend turnover days during the season.
  • January is a strong booking month because of the ferry ticket sales and many popular houses will book up quickly.
  • Rental homes are listed through out the season, to a certain degree, making last minutes bookings a strong possibility.

Sunset in Aquinnah

All in all, you should consider booking your Martha’s Vineyard vacation home ahead of time, especially, if you have specific criteria, price and dates in mind.  If you can be somewhat flexible, any time is a good time!  We have a house for you with over 500 listings in our inventory.

Martha’s Vineyard Vacation Rental: North Water Street, Edgartown

North Water Street, one of the most historic,  runs along the north side of Edgartown Harbor.  The street is lined with captain’s houses that date back to the whaling days and ends with The Harborview Hotel.

Being the last house prior to the hotel gives the guest of this house the versitillity of enjoying their own private vacation rental with the ability to utilize the restaurant amenities right next door.

Enjoy summer days on the front porch admiring the view of Edgartown Harbor with the Edgartown Lighthouse and beach just steps away.  Don’t like to lounge out front with an open view from the street?  No problem.  Lovely den on the upper level in the back of the house.  Can be used as office or just a quiet reading nook.

This property brings you back to what old Vineyard summers must have felt like (only with upgraded amenities for today’s comforts).  Perfect house for multi-generational family with separate guest accommodations off the back of the house.

Love this property, let me know what you think!

Welcoming the Holidays Edgartown Style

Edgartown Lighthouse at Christmas, by David Welch

Christmas in Edgartown weekend is my favorite way to get into the holiday spirit.  This is the 26th year we have been celebrating the weekend event.  It will be held on December 11-14, 2008.  There are so many activities for everyone!  The weekend is packed to entertain and enthrall adults and children alike.

My favorite event is the Evening of Enchantment at Donaroma’s Nursery just outside Edgartown center.  It is a stunning display that families big and small can enjoy at no charge.  They also offer boxwood tree and wreath decorating session throughout the weekend with a charge for supplies.

Donaroma's Nursery, Christmas in Edgartown

The streets of town are decorated, the shop owners welcome visitors with holiday cheer and you can even find some unique and special gifts to tick off your holiday shopping lists.

Minnesingers Holiday Concert, by David Welch

The mini singer concert is offered on Friday evening and Sunday afternoon at the Old Whaling Church right downtown.  It will truly warm even the grichiest of hearts.   Visit the Edgartown Board of Trade website to see a full schedule for the weekend.