Windwalker Rentals Blog - Nantucket Lifestyles

Amazing Rental Opportunity in Madaket!! Available for a longer rental of 8 days: July 3rd – July 11th.  Book now and receive 8 nights for the price of 7 and a FREE Vehicle Ferry Ticket to arrive in Nantucket on July 3rd and depart on July 11th. What better way to spend 4th of July than soaking up the sun and celebrating on Nantucket!

Enjoying stunning ocean views from the deck and the best sunsets on Nantucket, this  Nantucket beach house offers 4 bedrooms,  Air conditioning , and recently remodeled kitchen and baths with tumbled marble. Ideally located  approximately 400 yards to Madaket Beach.  Fall asleep to the sound of the Atlantic Ocean.  At your fingertips are beaches, the Madaket bike path and Millie’s Restaurant.

Follow this link for more information and photos.

HURRY -don’t wait too long  to book!









Nantucket is a busy place and if you are planning a summer vacation on our beautiful resort island, you may want to plan your stay around one of our many Nantucket events. The season kicks off with our Annual Daffodil Weekend in late April and closes with Nantucket Stroll weekend in early December. Whether you are looking for a cottage or a luxury home to rent, we’re looking forward to helping you plan an unforgettable vacation! Fulfilling your vacation needs is of the utmost importance to us – that’s why we’re always available to help you plan every detail of your dream getaway!


April 24-26 ~ Daffodil Weekend

May 13-17 ~ Nantucket Wine Festival

May 22-25 ~ Memorial Day Weekend

June 1-7~ Nantucket Restaurant Week

June 19-21 ~ Nantucket Book Festival

June 24-29 ~ Nantucket Film Festival

July 3-5 ~ 4th of July Weekend (4th is on a Saturday)

July 15-18 ~ Nantucket Comedy Festival

July 18-19 ~ Nantucket Triathlon

August TBD ~ Music Festival

August 8 ~ Boston Pops

August 8-16 ~ Nantucket Race Week

September 4-7 ~ Labor Day Weekend

September 24-27 ~ The Nantucket Project

September 28-Oct 4 ~ Nantucket Restaurant Week

October 10 ~ Nantucket Cranberry Festival

November 26 ~ Thanksgiving

December 3-6 ~ Nantucket Stroll Weekend


19 Broadway "Sconset

19 Broadway “Sconset


This charming, newly renovated Nantucket summer cottage in the heart of ‘Sconset village, offers old world ambiance with the convenience of a brand new kitchen and a recent au courant redecoration.  Featuring four bedrooms, 2.5 baths and boasting water views, steps to the beach and the ‘Sconset Market, this historic cottage is located just moments away from world-class dining that includes The Chanticleer, The ‘Sconset Cafe and the Summer House.  Everything that is Sconset awaits you here!

Prime summer weeks are still available -please contact one of our rental specialists for more information.

For more information on other ‘Sconset rentals follow this link

Since 2002, The Nantucket Atheneum has raised funds for their Weezie Library for Children by holding the Cold Turkey Plunge on Thanksgiving morning. Over 800 people will brave the cold waters of Nantucket Sound and take the plunge at

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Children’s  Beach. Prizes are awarded for teams, costumes, and family participation.

The Cold Turkey Plunge is a major source of funds for CD’s , books, and over 500 free programs and workshops for children that are held throughout the year at the Weezie Library.  Windwalker Real Estate is proud to be a 2014 sponsor once again and we urge everyone to join the fun!

If you are on the island for the Thanksgiving holiday, please support the Nantucket Atheneum’s Weezie Library for children by signing up for the plunge. You can pick up your Plunge Pledge Cards at the library, the Community Pool, The Westmoor Club, Espresso To Go, Nantucket New School & Nix’s Brew Pub.

To make a donation or to signup, please visit:

Beautiful evening at Cisco.

Beautiful evening at Cisco.

The fall months are a wonderful time to visit in Nantucket, the leaves are changing and the air is crisp. Columbus Day Weekend is upon us and a great time for a long weekend getaway to the Island. Whether you enjoy fine dining and shopping or an outdoor excursion, Nantucket is the perfect place. Upon your arrival to the Island take a stroll up Main Street and enjoy some of the best shopping offered anywhere; whether you you are looking for a new fall ensemble or the perfect gift for any occasion. Hepburn’s has great women’s clothing whether you are in the market for a cozy cashmere sweater or a great pair of Paige Denim jeans to put together a great weekend look. You can always count on “The Lovely”,  located on Washington Street, for the latest styles to compliment any occasion. Enjoy popping in and out of the shops along the cobblestone streets to discover some great accessories.

Once you finalize your fall wardrobe, take a trip out to Cisco  for an afternoon of Pumple Drumkin (their signature pumpkin beer) and Live Music at Cisco Brewers.  Enjoy the fall air while sipping on a beverage in a laid back atmosphere. This weekend enjoy live Music from “Earth Got The Blues,” a local Jazz and Blues Band. While you are there you can take a tour with the Master Brewer to see how they create their signature libations.

Harbor views from 2 Old North Wharf.

Harbor views from 2 Old North Wharf.

Many of our local restaurants in Town offer a variety of fall menus utilizing the local fare. Check out the menus at American Seasons and The Boarding House for their unique and contemporary dishes. Nantucket offers some of the most unique and creative cuisine employing our local farms and fishermen. Fall on Nantucket is great time of year for Scallops, enjoy a Nantucket Bay signature Nantucket Bay scallop creation with each restaurant having its own twist.

Looking for a place to stay for the long weekend check out some of our cozy in town Rentals available for Columbus Day and through October. 2 Old North is a signature property located in the heart of Town with views of the Harbor.

For additional rental information and other properties please contact us at


Nantucket Dolphins swimmers Gianna and Bella Quin with Olympic swimmer Kate Zeigler

Nantucket Dolphins swimmers Gianna and Bella Quinn with Olympic swimmer Kate Zeigler

Recently the Nantucket Dolphins Swim Team had the incredible opportunity to bring two Olympic swimmers to Nantucket for a clinic. The morning session featured a four hour swim stroke technique clinic in the pool for swimmers from ages 8 to 18.  In the afternoon, swimmers Ian Crocker and Kate Zeigler shared their inspirations followed by in-water instruction on technique and swimming strokes and a chance to challenge the Olympians to a race.  At the end of the clinic the Dolphins had the chance to have photographs taken with Kate and Ian and to get their autographs.

The Mutual of Omaha Breakout Swim Clinic visits over 90 cities each year offering an experience that inspires and motivates young swimmers. Mutual of Omaha is an official sponsor of US Swimming and supports US swimming on all levels.

The Nantucket Dolphins enjoyed the clinic as well as the experience of hosting the swimming champions with host families.

The Dolphins goal is to develop strong, safe, confident and successful swimmers while instilling attributes such as self-esteem, integrity, teamwork, sportsmanship in each swimmer through positive reinforcement and discipline.  It is their hope that the life lessons learned from the sport of swimming will transfer to the swimmer’s life outside of the pool.

The Nantucket Dolphins team began with twenty swimmers in 1990 and had only two swim meets. They  are now entering the beginning of their 24th season with 150 swimmers participating in their program last year.  They compete in the Southeastern Massachusetts Swim League (SEMSL) and are also affiliated with and are registered with United States Swimming.


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.


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