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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Modern Home With Classic Island Architectural Charm. Pool. Tennis.

Bedrooms 4
Half Baths1
Property type house
Minimum Stay 7 nights


About the property

4+ Bedroom, 4 1/2 Bathroom, Large Back Yard, Private Location, Pool & Tennis

Looking for the perfect vacation retreat with family and friends? Winding Down is the house for you! Located in Nashaquisset (less than a mile from Town and on the bike path to Surfside Beach), Winding Down enjoys a private location off a quiet cul-de-sac. Drive down the shell path and pull up to this beautiful home: four+ bedrooms (occupancy 8-10), open living room/dining room/kitchen, and three floors of living space (in addition to a ping pong table in the large basement) provide plenty of space for all to enjoy. A large deck overlooks the spacious back yard (which abuts conservation land), and a screened in back porch invites you to enjoy a serene breakfast before the day begins ... a leisurely lunch ... or casual supper after a day at the beach.

Amenities include use of Nashaquisset's pool and Har-Tru tennis courts; wifi throughout the house; outdoor hot shower; flat screen televisions in the den, master bedroom, loft; ping pong table in the basement; parking for two cars; bike rack; and more (see details below).


Living Room with fireplace

Dining Area


Half Bath

Den (with pullout couch and flat screen television)

Master Bedroom (with en suite bathroom and flat screen television)


Open loft with game table, flat screen television, comfortable seating

Bedroom 1: Queen bedroom with en suite bathroom

Bedroom 2: Large Twin bedroom (2 twin beds) with attached full bath


Large twin bedroom (2 twin beds), television, attached full bath


Large deck off dining area/kitchen with patio seating and gas grill

Outdoor hot shower

Screened in back porch with table & chairs

Back yard large enough for tossing balls around with the kids

- abuts conservation land.


Nashaquisset features two Har-Tru tennis courts, as well as a swimming pool and sundeck; use of these amenities is included in the listed rent. 'Winding Down' will be professionally cleaned in advance of your check-in; if you are staying multiple weeks, a cleaning will take place each week of your visit; further details are provided in your lease. Check-in time is 4pm; check-out is 10am. (Saturday turnover.) No Pets. No Smoking.

More Details

Property Manager
Suzanne Del Rossi
Member since: 2011
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
February 18, 2018

What makes this house unique

Winding Down was built by Steven Cohen, the developer of Nashaquisset. in the late 1980s/early 1990s. Designed to embody the diverse iconic Nantucket architecture found throughout the island, Winding Down is part of this special community of winding roads, picket fences, brick sidewalks, and privet hedges.


Nantucket Town House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Max. occupancy: 10
  • children welcome
  • pets not allowed
  • non smoking only
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer ...
  • Fireplace
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Telephone
  • Towels Provided ...
  • Washing Machine ...
  • Coffee Maker
  • Dishes & Utensils ...
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • seating for 8 people
  • 4 Bathrooms
  • 1 Half Bath
  • Master Bath - first floor - toilet , combination tub/shower , En suite
    Half bath - first floor - toilet
    Queen Bedroom - Second Floor - toilet , combination tub/shower , En suite
    Second Floor - Twin Room - toilet , combination tub/shower , Attached to bedroom
    Twin Bedroom - Third Floor - toilet , combination tub/shower , Attached to bedroom
    Outdoor Shower - shower , Hot water outdoor shower - off back deck of house
  • 4 1/2 bathrooms: First floor: Master Bathroom en suite to Master Bedroom Half Bathroom Second floor: En suite bathroom to queen bedroom Full bath attached to second (twin) bedroom Third floor: Full bath attached to third (twin) bedroom
  • 4 Bedrooms, Sleeps 10
  • Master Bedroom - First Floor - 1 king , En suite bathroom
    Den - First Floor - 1 sleep sofa /futon , Attached half bath
    Queen Bedroom - Second Floor - 1 queen , En suite bathroom
    Twin Bedroom - Second Floor - 2 twin/ single , Attached full bath
    Twin Bedroom - Third Floor - 2 twin/ single , Attached Full Bath
  • First Floor Master Bedroom: King bed First Floor Den: Pullout Couch, doors that close off room Second Floor: Queen Bedroom, en suite bath Second Floor: Twin Bedroom, attached bath Third Floor: Twin Bedroom, attached bath
  • Ping Pong Table
  • Satellite / Cable
  • Television ...
  • Deck / Patio ...
  • Golf ...
  • Lanai / Gazebo ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Tennis ...
  • wheelchair inaccessible
Pool / Spa:
  • Communal Pool ...
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
  • synagogues
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • kayaking
  • parasailing
  • pier fishing
  • sailing
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • wind-surfing


Exceptional! 5/5 -
(10 traveler reviews)

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Modern Home With Classic Island Architectural Charm. Pool. Tennis.
average rating of 5.0 based on 10 reviews

Wonderful family vacation

  • 5 of 5

This was the perfect place for a family getaway - my brother and his family, my father and our family all went together and had such a fantastic time. The kids (13,12,8,5) had a great time together playing in the house and the backyard, and the house was convenient by bike to several beaches. Very enjoyable family time, great location, and great communication from Suzanne made this a terrific VRBO experience.

  • Submitted: Jul 8, 2017
  • Stayed: June 2017
  • Source: VRBO, from HomeAway
Owner's Response: Mary Pat: We are so glad you enjoyed your stay at Winding Down! We hope you'll visit us again ... you and your family were wonderful rental guests! S.
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Best of the Best!

  • 5 of 5

Winding Down is so wonderful in so many ways. The house is extremely well laid out and afforded our two families plenty of room to spread out. The loft was great for the teenagers and there were 2 masters which were fantastic for the parents. We had great family dinners at the dining table and were able to grill out on the back deck while we watched our younger ones kick the soccer ball around in the private pack yard. The sun-filled front yard was perfect for morning coffee.

What we really loved was the proximity to town and beaches. Some of us frequented town while me and the boys hit Cisco or Nobadeer for surfing.

The house is well appointed, we thoroughly enjoyed preparing our family meals, often packing up coolers for the beach and our trip to Great Point. The house beach chairs were great as we used them quite often.

If you are lucky enough to get this house make sure you make a trip around the corner for fresh made doughnuts at the Downey Flake! If your not toooooo tired in the evening you can catch some great live music at the Chicken Box. (just a hop skip and a jump from the Downy Flake)

We were sad to pack it up at the end of our stay - but are looking forward to a return trip!

An awesome vacation on all accounts, a wonderful home away from home!

  • Submitted: Jul 15, 2016
  • Stayed: July 2016
  • Source: VRBO, from HomeAway
Owner's Response: Yes - one of Winding Down's best features is its location on the island: walk to Town (less than a mile away) ... enjoy a great breakfast at the DownyFlake .. and listen to live music at the Chicken Box ... walking is a great way to get around when you're staying at the house. Glad you had a great vacation; we look forward to seeing you again!
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The best location on the island!

  • 5 of 5

Winding Down is the perfect house for my family - we stayed there one year ago and are getting ready for our next visit in a few weeks.

There is plenty of room for everyone to relax when together. Furnishings are clean and comfortable; everything we needed was at our fingertips. We appreciate the heated pool, and the tennis courts were a great place to introduce our children (7 and 9) to the game.

The location is great: less than a mile from Town … a nice walk to the Juice Bar for an after-supper ice cream cone and to shopping and restaurants.

Suzanne made the whole reservation process easy - and was available before and during our stay for questions and concerns.

Can’t wait to get back to ACK - and to Winding Down!

  • Submitted: Jun 9, 2016
  • Stayed: June 2015
  • Source: VRBO, from HomeAway
Owner's Response: Winding Down IS a great place to vacation - especially because of its location on island. I'm always happy when our guests are happy - we do everything we can to make their stay comfortable and worry-free!
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Ideal Family Vacation

  • 5 of 5

Each person in our entire three generation family had a truly outstanding vacation at Winding Down. Every aspect in the owner's description is accurate, with meticulous and clean condition in every room. There are plenty of bathrooms and family areas for privacy and separate enjoyment . When we had minor issues, a person repaired them the next morning. The community pool was perfect for our grandchildren and our granddaughter (age 7) enjoyed riding her bicycle in the blocks around the house, which is convenient to the Town as well as many beaches and neighborhoods of Nantucket. In order to preserve the clean and well stocked condition of the house, the landlord has many rules for maintaining the property and replacing all supplies, so enjoying the house comes with more responsibilities than some other houses.

  • Submitted: Oct 7, 2015
  • Stayed: September 2015
  • Source: VRBO, from HomeAway
Owner's Response: Winding Down offers many "stretch out and relax" areas for large group gatherings - and the neighborhood is great for kids of all ages! We do ask our guests to replace items they've consumed (e.g., paper towels, dish detergent, etc) before they leave so that those following them will arrive to a well-stocked house ... a courtesy that has always been appreciated by our many renters!
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peabody, MA


  • 5 of 5

This is a large yet cozy home in the village of Nashaquisset....who doesn't want to be near the pool, the beaches, and Town????

  • Submitted: Apr 21, 2015
  • Stayed: September 2014
  • Source: VRBO, from HomeAway
Owner's Response: You're right - Winding Down is in a great location on the island ... especially for those who decide to come without a car. It's easy to hop onto the bike path - you can walk into Town (less than a mile away) - a major grocery store is less than 1/2 mile away ... glad you enjoyed your stay!
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Lexington, MA

Wonderfully comfortable vacation home!

  • 5 of 5

We love Nantucket in September ... and we LOVED staying at Winding Down for a beautiful week on island. The house was immaculately clean, substantially furnished with beach towels, beach chairs, linens, towels, and more - the amenities (including a great location) made renting this house a real value. Hope to be back again soon!

  • Submitted: Apr 20, 2015
  • Stayed: September 2014
  • Source: VRBO, from HomeAway
Owner's Response: We are so glad you enjoyed your visit ... Nantucket is beautiful ANY time of the year, but especially in September! We look forward to seeing you again!
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Nearest Airport
7 Miles
Nantucket Airport
Nearest Barpub
0.5 Miles
Too many to list! :)
Nearest Ferry
2 Miles
Steamship Authority
Nearest Golf
2 Miles
Miacomet Golf Course
Nearest Restaurant
0.5 Miles
Island Kitchen, The Sea Grille, DowneyFlake
Nearest Beach
2 Miles
Surfside Beach
Car: not necessary

Winding Down is located in the Nashaquisset neighborhood - conveniently located less than a mile from Town and on the bike path to Surfside Beach. Large grocery store, restaurants, and shops available half mile away.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $800

Cancellation Policy: Money will be refunded in full (less a $200 cancellation fee) if the week(s) can be re-rented at same amount. Rental guest might want to consider travel insurance if cancellation is a possibility.

Rates are subject to change until reservation confirmed. Personal or bank checks only. Two payments may be made (half of total amount due within one week of receiving lease by email; final payment due by March 1, 2017). After March 1, 2017: payment due in full within one week of receiving lease by email.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.

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