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

Nantucket Town, Nantucket, MA, USA
  • House
  • Bedrooms4
  • Sleeps10
  • Bathrooms4
  • Half Baths1
  • Minimum Stay7 nights

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.

Property Manager

Suzanne Del Rossi

Member Since 2011
Response rate:
Response time:
within a few hours
Calendar last updated:
Mar 07, 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.


    • Internet
    • Air Conditioning
    • Fireplace
    • Satellite or Cable
    • Kids Welcome
    • Washer & Dryer
    • Parking
    • TV
    • No Smoking


      • 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


      • 4 Bathrooms, 1 Half Bath
      • Master Bath - first floor
        toilet, combination tub/shower, En suite
      • Half bath - first floor
      • 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


        • Away From It All
        • Family
        • Historic
        • Romantic
        • Sports & Activities
        • Tourist Attractions


            • Guests provide their own meals


                • Linens Provided
                  Two sets of sheets per bed provided.
                • Air Conditioning
                  Central air conditioning
                • Fireplace
                • Hair Dryer
                • Internet
                  Wifi throughout the house
                • Iron & Board
                • Clothes Dryer
                  Large new dryer available in basement.
                • Living Room
                  Large open living room with two-story ceiling.
                • Parking
                  Parking for two+ cars in driveway.
                • Telephone
                • Towels Provided
                  Two sets of towels per occupant provided.
                • Washing Machine
                  Large new washing machine available in basement.


                    • Coffee Maker
                    • Dishes & Utensils
                      Dishes, glassware, utensils provided.
                    • Dishwasher
                    • Kitchen
                      Large kitchen with all appliances (large and small) needed for every cooking experience!
                    • Microwave
                    • Oven
                    • Refrigerator
                    • Stove
                    • Toaster


                        • Dining Area
                        • comfy seating for 8 people


                            • Ping Pong Table
                            • Satellite / Cable
                            • Television
                              Flat screen televisions in den, Master Bedroom, loft. Regular television in third floor bedroom.


                                • Deck / Patio
                                  Spacious deck in back yard with patio chairs/chaises.
                                • Golf
                                  The island's golf courses are in close proximity to Winding Down.
                                • Lanai / Gazebo
                                  Screened in porch off kitchen.
                                • Lawn / Garden
                                  Large back yard, perfect for games. Abuts conservation land.
                                • Outdoor Grill
                                  Large gas grill.
                                • Tennis
                                  Nashaquisset features two Har-Tru tennis courts - among the best on the island!


                                    • wheelchair inaccessible

                                      Pool / Spa

                                        • Communal Pool
                                          Beautiful sundeck and changing rooms.


                                            • live theater
                                            • churches
                                            • festivals
                                            • health/beauty spa
                                            • library
                                            • cinemas
                                            • marina
                                            • museums
                                            • playground
                                            • restaurants
                                            • synagogues

                                              Leisure Activities

                                                • shelling
                                                • antiquing
                                                • bird watching
                                                • boating
                                                • photography
                                                • scenic drives
                                                • beachcombing
                                                • shopping
                                                • sight seeing
                                                • walking
                                                • whale watching
                                                • wildlife viewing

                                                  Local Services & Businesses

                                                    • ATM/bank
                                                    • groceries
                                                    • hospital
                                                    • massage therapist
                                                    • medical services

                                                      Sports & Adventure Activities

                                                        • snorkeling
                                                        • cycling
                                                        • fishing
                                                        • golf
                                                        • kayaking
                                                        • parasailing
                                                        • pier fishing
                                                        • sailing
                                                        • deepsea fishing
                                                        • snorkeling/diving
                                                        • sound/bay fishing
                                                        • surf fishing
                                                        • surfing
                                                        • swimming
                                                        • tennis
                                                        • wind-surfing

                                                          10 Reviews


                                                          Latest reviews

                                                          Wonderful family vacation

                                                          Mary L.

                                                          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.

                                                          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.

                                                          Best of the Best!

                                                          Glenn C.

                                                          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!

                                                          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!

                                                          Ideal Family Vacation

                                                          Frederic J.

                                                          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.

                                                          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!

                                                          The best location on the island!

                                                          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!

                                                          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!

                                                          Wonderfully comfortable vacation home!

                                                          SeptemberSunLexington, MA

                                                          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!

                                                          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!


                                                          Vacation Valpeabody, MA

                                                          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????

                                                          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!


                                                          Nantucket Town, Nantucket, MA, USA

                                                          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

                                                          Additional information about rental rates

                                                          Cancellation Policy: Money will be refunded in full (less a $300 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.

                                                          10 Reviews
                                                          Exceptional 5/5
                                                          Enter dates for accurate pricing
                                                          For booking assistance, call 888-640-7927

                                                          Property # 680668