Windwalker Rentals Blog - Nantucket Lifestyles


Nantucket Fall Rental

16 Pleasant St. Nantucket 02554

This  beautifully appointed Nantucket vacation home, located just a block from Main Street shopping and world class restaurants could be yours  for a fantastic fall stay. This property maintains the traditional features of an historic  Nantucket cottage built in 1790 while maintaining  modern amenities. Spacious rooms and comfortable living spaces are complemented by antique wooden floors and fireplaces throughout. A beautifully landscaped garden and patio offer a wonderful spot for dining al fresco or relaxing with a book.

Enjoy all that Nantucket Town has to offer during our best kept secret-Fall on Nantucket.  For more information follow this link 


The Boston Pops comes to Nantucket to perform on Saturday, August 9th.  Enjoy an evening of music and fireworks on the beach under the stars to benefit Nantucket Cottage Hospital hosted by David Gregory. For more information

The gates open on Jetties beach at 4:30. Concert from 7:30 to 9:30 and Fireworks at 9 pm. PopsLogo_graybackground


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Jennifer Shalley & Justin Quinn (missing from photo Leone Collins)

Windwalker Real Estate was well represented this weekend at the 2014 Triathlon on Nantucket.  Participating in the sprint distance Triathlon on Saturday were Justin Quinn, Jennifer Shalley and Leone Collins. In the last three  years, the Nantucket Triathlon has donated $100,000.00 to the Town of Nantucket Scholarship Fund to provide scholarship opportunities for Nantucket students.

Jenny Paradis

Jenny Paradis








Special kudos go to Windwalker’s Jenny Paradis who participated in the Olympic distance Hero Triathlon on Sunday! The primary purpose and drive behind the HERO TRIATHLON SERIES is to help the  people who fight for our freedom and to support and raise funds for the Women’s Veterans Network of Massachusetts.


Avoid the emergency room by taking advantage of the the new walk in care clinic at the Nantucket Cottage Hospital. The clinic is located at the Nantucket Cottage Hospital at 57 Prospect St. in the Anderson building. Please see below for walk-in care dates and times.


With Tropical Storm Arthur poised to potentially bring bad weather to Nantucket on July 4th, the Town has postponed fourth of July activities to July 5th.  Please see the press release below for further information.fourthofjuly2014prstorm

This extraordinary ocean and harbor front Nantucket beach home features panoramic water views from every window. Situated on a pristine beach, steps to sand dunes and water. Enjoy outdoor sunning, stargazing and majestic sunsets from ample deck space. Proximity to Millie’s restaurant and country store. This home sleeps six and has a modern style and is very comfortably furnished. Due to the location of this beach front property a four wheel drive vehicle is needed to access the property.

45 Mass Ave - Vacation Property Nantucket (4)

45 Mass Ave - Vacation Property Nantucket (2)

Enjoy your  Nantucket vacation on this quite lane in Brant Point.   This four bedroom Nantucket vacation summer home  is just minutes to town and the beach. An abundance of natural light, wonderful outdoor living space perfect for outdoor dining or lawn games.  Outdoor shower. Availability for July and August.

Nantucket Summer Rental

54 North Beach - Nanctucket Vacation


Jetties Beach is located in the Brant Point neighborhood near Town and is a great attraction year-round on Nantucket. The beach is most obviously named for the jetties that mark the opening of Nantucket Harbor.  The jetties were constructed in the late 1800′s out of New England Granite.  To see the full history, visit the Nantucket Historical Association.

One of the reasons this Nantucket  beach is so popular, is that it boasts the only public tennis courts on island, as well as a family friendly restaurant, beach store, restrooms, playgrounds, parking and a lifeguarded beach. At Jetties Beach you can watch the ferries round Brant Point and come into Nantucket Harbor, and get in your afternoon tennis game. Jetties is also special because it is one of the more handicap accessible of the beaches as it has a boardwalk leading most of the way down to the water.

Since Jetties is a harbor beach, the water is warmer and calm, with little to no waves – except when the tide changes (a word of caution – when the tides are changing the undertow can be quite forceful).

Jetties Beach can easily be accessed by bike, foot or WAVE shuttle .   If you choose to drive and you arrive early in the day, you should have no trouble parking.

Jetties is located just a short distance from Town, The Cliff and Brant Point, all ideal spots for a summer home.  If you are contemplating a purchase or searching for a summer rental, please contact one of our associates for expert advice.







Madaket Sunset -Photo courtesy of Bill Kantor

Madaket Sunset -Photo courtesy of Bill Kantor

The most notable attraction in Madaket is quite simply the stellar sunsets.   Imagine passing the day at the beach and ending it with evening beach picnic while viewing the sun bidding the East Coast adieu in a kaleidoscope of colors. After spending a day relaxing on the beach, you can always pop into Millie’s Restaurant .  In addition to a full dinner menu, Millie’s offers sunset views and a signature drink, that is not to be missed. (In fact, if you find yourself needing anything at all in Madaket, Millie’s  mini market is the only outpost on the western end of the island).

Madaket is also known for several other outdoor activities.  Many enjoy swimming in the surf, beach combing for treasures, taking in the history of Madaket Millie, fishing from the shore for striped bass and  even birding.  Madaket is extremely special because it has both surf beaches and harbor access for those who enjoy calmer waters.

From Smith’s Point and Hither Creek, you can capture a view of Tuckernuck Island.  Tuckernuck is a tiny island off the Madaket coastline that is home to a handful of simple summer homes designed to be fully functional using generators  for power.

Whatever your style,  you are sure to be enchanted by Madaket. If you decide to reserve your vacation rental in another area, be sure to visit Madaket at least one evening for a unforgettable evening display of vivid color.

Search our entire Madaket rental inventory here.You may also browse properties for sale in Madaket.

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On Friday, April 25th the Oates-Euler collection opens to the public at the Nantucket Historical Association. This major exhibition in collaboration with Artists Association of Nantucket chronicles the creative life of Andy Oates and Bill Euler. Amongst the artists and artisans that came to Nantucket in the sixties, collectors Andrew Oates and William Euler were at the heart of  this transformative time. “Andy and Bill’s vision epitomized  by decades of collecting crafts and fine arts—fueled an island lifestyle based on the beauty and simplicity of cottage-style living.” On Thursday, April 24th,  the AAN curator of the exhibit, Bobby Frazier will give a sneak preview of the exhibit as a part of the NHA’s  Food For Thought Series.



10151878_10152779742824689_4345924186319345816_nNantucket Cottage Style: Drawing Inspiration from  on Friday, April 25, during regular museum hours. But you can get a behind-the-scenes look on Thursday at noon during Food for Thought, when we welcome Bobby Frazier, the curator of the exhibition. Don’t miss this exciting look inside the estate of collectors Andy Oates and Bill Euler!

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