Windwalker Rentals Blog - Nantucket Lifestyles

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Relax on secluded and oceanfront Sheep Pond Road and take in all that Madaket has to offer!

This quiet, beautiful beach house has multiple ocean views of the Atlantic, a scenic outdoor area and multiple decks to enjoy the waterfront serenity or the picturesque sunsets.  There are three bedrooms and two full bathrooms.

The first floor includes a renovated living room facing the ocean with a wood-burning fireplace; large, renovated eat-in kitchen and dining room with French door opening to the deck; two bedrooms with a shared full bath; plenty of outdoor living space.

Upstairs is a spacious master bedroom suite with beautifully tiled master bath; cathedral ceilings; walk-in closet; fireplace; and French doors to a deck facing the ocean.

26 Sheep Pond still has prime Summer 2016 availability!  Contact your Windwalker William Raveis agent or email to book your Nantucket dream vacation!

Learn more about this rental here:

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The Tidewater Cottages are located in the heart of Nantucket’s historic village, just moments from downtown and Washington Street Beach. It’s a perfect setting for those seeking proximity to downtown restaurants and shopping  along with everything the waterfront has to offer.  For those looking to experience different areas of the island, the property also includes off-street parking.

These charming cottages feature brand new high end amenities and are designed in a contemporary Nantucket style. Both Units A & D are beautifully  furnished with harbor views. The top of the line finishes include walnut trim, quartz counter tops and ship lap paneling throughout. Take in a sunset on your  private deck overlooking the Harbor. These units cater to both couples and families to enjoy Nantucket during any season. These brand new cottages have open availability today for the 2016 Season, book now and enjoy luxurious Nantucket accommodations!

Contact Windwalker William Ravies for More Details.


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Hurry, only 1 week left to rent in this fabulous Cliff Compound! Main house with three levels of living: four generous ensuite bedrooms, gourmet kitchen, beautiful second floor views of the North Shore, fully finished lower level with media room, wrap-around porch, and outdoor shower.  Plus an enchanting Guest cottage with 2 ensuite bedrooms, living room, kitchen, private deck and outdoor shower. Ideally located near walking and biking trails, pristine North Shore beaches, shopping and world-class dining in Nantucket Town.


Recently added, in-ground pool privately surrounded by a stone wall and perennial plantings.

For more information and photos follow this link or contact one of our expert rental agents to book now!


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 best online casino 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 online slots 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 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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