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Home on Hill with Views of 18th-Century Working Windmill and Town

Carolyn Crowley

Member since: 2001
Call Owner
Enter your email address to view the phone number
Speaks: english
Bedrooms 4
Half Baths1
Property type house
Minimum Stay 7 nights

Carolyn Crowley

Member since: 2001
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
May 23, 2015
Call Owner
Enter your email address to view the phone number
Book with confidence
Book with confidence
Guaranteed, secure, with no booking fees
Add vacation protection services to your booking
Three services to protect your trip:
Protect your payments in case you need to cancel.
Guarantee the rental meets your expectations
Ensure you're prepared in case of accidental damage.

Home on Hill with Views of 18th-Century Working Windmill and Town

Bedrooms 4
Half Baths1
Property type house
Minimum Stay 7 nights


Nantucket Town House Rental Photos and Description

4 BR, 2.5 BA, sleeps eight. Six twins, one king four-poster bed.

IMPORTANT NOTICE: Homeowner has boat tickets to and from Nantucket for guests' cars.

Windswept--aptly named--sits atop Mill Hill in Nantucket Town's Residential Old Historic District on one acre facing a quiet, 18th-Century working windmill. Air-conditioned Windswept is a 10-minute delightful walk--only two turns--to shops, restaurants, theaters, beaches and a two-minute walk to the Island-wide shuttle bus stop and bike paths. With Windswept's superb location, no car is necessary but Windswept has two off-street parking spaces.

Windswept is available weekly, bimonthly, and monthly. Families can enjoy Windswept alone or with the nearby air-conditioned, secluded, romantic, and cheery one-bedroom house (see # 105380) for multigenerational reunions. This family compound sleeps 12.

Windswept, at the end of a long, winding driveway with blackberry bushes, has a wraparound porch with teak Adirondack chairs and ottomans, two picnic tables and benches, an eat-in kitchen, separate dining room, gigantic living room, mammoth master bedroom with sitting area, wireless Internet, spacious yards to play games and hold family sports tournaments, charcoal grill, stereo system, fireplace, Oriental rugs, outdoor shower and hardwood floors.

Windswept also has complimentary Internet (Wi-Fi), fresh flowers, an enclosed outdoor hot/cold after-swim shower with a spacious dressing area; beach chairs which can be worn on your back to hold a cooler and your belongings for a day at the beach; beach towels; beach coolers (three sizes); microwave oven; toaster; Cuisinart; blender; Crock-pot; lobster pot; fish poacher; three cable flat-screeen HDTVs; DVD player; VCR; 10-CD changer/tape/radio system; books; croquet, badminton, and volleyball; board games; and five hair dryers.

Caretaker: The caretaker lives nearby and responds quickly to tenants' requests, thereby ensuring guests' comfort and enjoyment. For a small fee, the caretaker will buy groceries and supplies to stock the refrigerator before the tenants arrive. Windswept's owner can recommend a responsible, experienced babysitter.

More Details
  • Long-term Renters Welcome
  • children welcome
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible
Carolyn Crowley (Owner)
Member since: 2001
Call Owner
Enter your email address to view the phone number
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
May 23, 2015

About Carolyn Crowley

I taught English as a Second Language in Japan (1968-1970), volunteered with Peace Corps in Morocco (1972-1974), taught fourth grade on Long Island, taught seventh and eighth grade English in Baltimore, substitute taught in Boston, and my favorite of all my jobs: I wrote newspaper and magazine stories 1980-2011 in Washington, D.C. I moved to Windswept September 2011.

Like my parents and our tenants, I love Windswept. It lacks nothing and is as comfortable as a home should be.

Carolyn Crowley purchased this house in 1965

Why Carolyn Crowley chose Nantucket Town

My mother fell in love with Windswept as soon as she walked through the front door. My father wanted to live on the 'Sconset Bluff. Thankfully Mom won. They both loved Windswept and Nantucket so much that they retired in Windswept when Dad retired at age 70 as a Boston Globe editorial writer.

What makes this house unique

Windswept is close to several beaches and is in Nantucket Town where tenants will want to shop, dine, attend theatrical performances and movies. Because it is on one of Nantucket's highest points, Windswept enjoys refreshing summertime breezes throughout the day and night. In one of Nantucket Town's largest yards--an acre--guests can safely play croquet, badminton, volleyball, soccer and football far from the street.

No house on Nantucket has better views of The Old Mill. Tenants love relaxing on the wraparound porch, reading, eating conversing with each other and gazing at the quiet windmill which grinds corn. The large wraparound porch has Adirondack chairs and ottomans, rocking chairs, picnic tables and teak chairs. Lawn chairs and picnic tables lie throughout the large front and back yards.

Guestbook comments from the owner

I would definitely stay here again. The location is great. We spent several afternoons enjoying champagne on the main house's well-appointed wraparound porch watching the sunset and enjoying the breeze in front of the windmill. Also, it's very easy to get into town (a 3-min. bike ride down the hill or a 10- minute walk), and returning up the hill is enough as to feel like it's a country estate. Both the main house (Windswept) and the nearby smaller house (In the Lee) were charming inside and out and very clean. Further, the houses were more than accommodating to our large group. We were at max occupancy--12--but it didn't feel like it. The houses make for a perfect base of operations for a fun Nantucket vacation with family or friends.

Jun 2010
  • 1 of 2

Why HomeAway

Bedrooms 4
Half Baths1
Property type house
Minimum Stay 7 nights
Book with confidence
Book with confidence
Guaranteed, secure, with no booking fees
Add vacation protection services to your booking
Three services to protect your trip:
Protect your payments in case you need to cancel.
Guarantee the rental meets your expectations
Ensure you're prepared in case of accidental damage.


based on 7 traveler reviews

Write a Review
Home on Hill with Views of 18th-Century Working Windmill and Town
average rating of 4.714286 based on 9 reviews

wonderful 2 weeks stay in Nantucket home

  • 5 of 5

Our family of 5 (19, 18, 16 year olds) had a wonderful 2 week stay at Windswepy this past August. It was everything the online description said and more. The home was very clean and well maintained. We had wonderful sleeps between the comfortable beds and bedding, wind that blows as the home is on a hill. There were plenty of sitting areas inside the home and out to enjoy a good book, play a board game, work on a puzzle as a family, all of which were provided by the owner. Ample beach toys and chairs were easily accessible in the basement which had a door and a few stairs rising up to the side sitting area by the car park - so convenient. The lawns around the house provided outdoor space as well for badminton, soccer and a frisbee game. The location was perfect - walk or ride bikes to town. close car ride or bike ride to all amenities, easy bike ride to surfside beach, and to yoga. The owner was very helpful providing suggestions re restaurants and activities, answering any questions in a timely manner and helping us with logistics (eg. mailing us forgotten item, helping with ferry logistics). We definitely would recommend this to family and friends and would love to return next summer. Almost forgot.. the outdoor shower is amazing!

  • Submitted: Sep 13, 2014
  • Stayed: Aug 2014
  • Source: HomeAway
Owner's Response: We certainly enjoyed having this family stay in our main house. They are talking about returning next year and we welcome them. Carolyn Crowley


  • 3 of 5

On the plus side, the house is true Nantucket in flavor and amenities, tastefully decorated with most needs met - kitchen items, games, etc. Wonderful porches. The BUT relates to the owner who was mostly pleasant and responsive to our needs, including getting a dehumidifier b/c t he basement bedroom was unpleasantly damp. She was on site pretty much daily to remove trash and recyclables and accused us of losing the grill cover which was folded neatly inside the basement, 'tho she later recanted that. She insisted that we vacate the property in advance of the 10 a.m. departure time as stated in the rental agreement. The serious problem was that despite our leaving this house in absolutely impeccable condition - bathrooms and kitchen totally clean, with laundry done and linens folded and put away or in a basket for bed-making, which she insisted she wanted to do. The only exception was that the rugs were not vacuumed due to a disgusting vacuum cleaner that spewed dirt and dust into the room. Then, she deducted most of the deposit which constitutes outright theft in our opinion. There is no way she and her cleaners could have spent the many hours she claimed. She implied she would credit me the amount if I rented from her again in 2014. What? Our family has rented on Nantucket for decades and never encountered a situation like this; rather, have been told by other owners that we have been excellent stewards of their houses. All in all, the house is nice but the ending was very disappointing. Future renters BEWARE.

  • Submitted: Feb 6, 2014
  • Stayed: Aug 2013
  • Source: VRBO, from HomeAway
Owner's Response: This grandmother brought her extended family to our home for one August week last summer. They had a most enjoyable time, which she confirmed to me on several occasions -- both during and after her stay at Windswept. She wrote in an e-mail, ". . .all is well. We very much enjoyed our stay at Windswept and your willingness to accommodate our needs was most appreciated." In another she wrote, ". . .thank you so much for all your efforts to make our stay at Windswept as enjoyable as possible. You met every need and request possible." However, she has complaints which came out of the blue, six months after her departure. Theft from the security deposit is her most outrageous charge. I handled her security deposit no differently from the 21 other tenants who have given me and my two HomeAway and VRBO homes five-star reviews. The tenant reviewers praise our homes' cleanliness, as this grandmother also did when she complimented me in an e-mail on the "organized and lovely way you presented your house to us." Soon after she left Windswept, I returned her security deposit---$760 (which is $240 from $1,000). So, "most of the deposit" was NOT deducted. Moreover, there was no "outright theft," as she claims in her review. She asked that I return "what will total close to the $1,000 you held" because, she wrote, there was "absolutely no need to spend more than two hours" to clean after eight people had stayed in our four-bedroom, 2.5-bathroom, three-story house, with an expansive wraparound porch, its tables and chairs, outdoor furniture and a grill. It takes two hours or longer to clean our much smaller one-bedroom cottage. NEVER in the many years since the 1990's that I've managed this house has the cleaning bill been for only two hours. Impossible. Her cleaning bill was in the $200-$300 range I quoted to her before she signed and sent the lease. My houses are clean for incoming tenants. I clean with the cleaners, pay them what they charge me and ask that tenants pay their cleaning bills. This tenant is the only one to complain that I deducted too much money from her security deposit. I didn't. She got the correct amount returned to her from the security deposit.

Windswept on Nantucket

  • 5 of 5

Windswept is a beautiful home in an excellent location. The home is bright and cheery and has everything you need to enjoy Nantucket. The house is stocked with board games, yard games and beach toys; leaving 4 young children occupied and happy. When the children went to bed, the front and side porch provided a charming and peaceful environment to relax and enjoy the sea breeze.

Windswept is just a short walk to town and a leisurely bike ride to some of the most fun beaches on the island.

The owner gave us many great suggestions about where to eat and points of interest that must not be missed. It was a wonderful trip that left us daydreaming about our return!

  • Submitted: Oct 10, 2013
  • Stayed: Aug 2013
  • Source: HomeAway

Wonderful Week in Windswept

  • 5 of 5

We rented Windswept for a week this past August and had a wonderful time. We have 3 children and the house was perfect for our family. The location is great because you can easily get to town, and at the same time, the yard is so big you have ample space for kids to play. One of our favorite features was the wrap around porch - we had breakfast and dinner here almost everyday. The house is equipped with all the beach necessities you need. In addition, the house was very clean and in great shape. I highly recommend renting Windswept on Nantucket.

  • Submitted: Oct 8, 2013
  • Stayed: Aug 2013
  • Source: HomeAway

Perfect Family Vacation!

  • 5 of 5

We had a wonderful vacation at Windswept. Not only is it a well-decorated, clean and fully stocked home oozing Nantucket charm, but also it is centrally located-- within walking distance to town and an easy bike ride to all parts of the island. We didn't even have a car-- with our two college-aged sons, we biked everywhere. It was a full week, starting with the Boston Pops benefit for Nantucket cottage hospital at Jetty's beach, evening bocce games on the lawn, trips to the local seafood market for fish to grill or lobster to boil, bike rides to a variety of beaches (with beach chairs on our backs from the house!), delicious dinners at the great restaurants in town, evening walks and ice cream at The Juice Bar. The boys met up with college friends at The Chicken Box and we'd sit on the porch admiring the sunset and the gorgeous old windmill in the evening. And we slept so well on the comfortable beds and breezes from the house's hilltop position. Caroline is a wonderful host, sharing her family home and all the island has to offer. It could not have been better!

  • Submitted: Sep 10, 2013
  • Stayed: Aug 2013
  • Source: HomeAway

a piece of heaven

  • 5 of 5

As soon as our family walked into Windswept, we felt at home. THere was nothing that we needed to add to the home. The owner provided everything to make our week stay feel like home. From the beach chairs, to frisbees, down to a full spice rack!!

My husband was able to comfortably work in the dining room and had easy internet accessibility.

Our 3 boys (16, 14, 11) would say, "I loved sitting on the porch each morning and enjoying the view of the windmill". Another son, "loved all the beach games and playing chess each afternoon after a full day of biking or beaching it". Another son loved the "easy bike ride each day into town or our evening stops for ice cream."

We are all waiting impatiently for next summer.

Windswept was truly a piece of heaven.

  • Submitted: Nov 8, 2012
  • Stayed: Aug 2012
  • Source: HomeAway


Galley Beach
Nearest Airport
3 Miles
Nantucket Memorial Airport
Nearest Ferry
1 Miles
Steamship Authority
Nearest Golf
2 Miles
Miacomet Golf Course
Nearest Restaurant
1 Miles
Nearest Beach
1 Miles
Jetties Beach
Car: not necessary

Natural history/museum tours, biking, family/fishing boating, sailing, surfing, tennis, golf, kayaking, snorkeling, bird watching, seal/whale/lobster cruises, crabbing trips, aquarium/observatory viewing, wildflower and ghost walks, laning, kiting, art classes, theater productions, beach combing (for shells, beach glass, and 'mermaid purses, outdoor family concerts (Boston Pops plays every August at Children's Beach), visual arts displays, auctions, tie-dying clinics, soccer/baseball/field hockey/basketball/lacrosse camps, lectures, scalloping and musseling.

Other Activities: auctions, winery tours, sports camps, moor walking, bird watching, star gazing, nature studies, fine dining, crabbing, seal/whale-watching cruises.


Rates & Availability

From $6,500 Per week

Nantucket Town House Rental Rates

Rental Basis:
per property
Rental rates quoted in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Early July
Jun 27 2015 - Jul 3 2015
7 night minimum stay
Jul 4 2015 - Jul 18 2015
7 night minimum stay
Late July
Jul 19 2015 - Jul 31 2015
7 night minimum stay
Peak Summer
Aug 15 2015 - Aug 22 2015
7 night minimum stay
Mid-Aug. to Early Sept.
Aug 23 2015 - Sep 5 2015
7 night minimum stay
Labor Day Week--Reduced
Sep 6 2015 - Sep 12 2015
7 night minimum stay

Additional information about rental rates

Refundable damage deposit $1,000.00
Notes Refundable Security Deposit: $1,000. Saturday to Saturday rentals. Check-in: 3 p.m. Checkout: 10 a.m. No pets, no smokers.
Homeowner has transferable boat tickets to & from Nantucket for guests' autos.
Rent Windswept alone or with nearby one-bedroom, one-bath, air-conditioned, secluded, and cheery house (see property listing #105380). This magnificent family compound in Nantucket Town sleeps 12.

Cancellation Policy

Policy available by contacting owner when booking.
Enter dates to see total


Nantucket Town House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 2500 sq. ft.
Location Type:
  • Monument View ...
  • Near The Ocean
  • Ocean View ...
  • Town
  • Away From It All
  • Family
  • Historic
  • Activities Guide
  • Air Conditioning
  • Alarm Clock
  • Backpack
  • Basic Soaps
  • Ceiling Fans
  • Clothes Dryer ...
  • Fireplace
  • Free Local Calls
  • Free Long Distance
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided ...
  • Living Room ...
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking
  • Parking Off Street ...
  • Telephone ...
  • Thermos Bottle
  • Toilet Paper
  • Towels Provided
  • Washing Machine ...
  • Wireless Internet ...
  • Wood Fireplace ...
  • 4 Ring Stove
  • Blender
  • Catering Available ...
  • Coffee Maker
  • Cooking Utensils ...
  • Dishes & Utensils
  • Dishwasher ...
  • Freezer
  • Grill
  • Kitchen ...
  • Lobster Pot
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Stove
  • Toaster
  • Dining ...
  • Dining Room
  • seating for 8 people
  • 2 Bathrooms
  • 1 Half Bath
  • Bathroom - toilet , combination tub/shower
    Bathroom - toilet , shower
    Bathroom - toilet
    Exterior - outdoor shower , Enclosed, hot/cold water, large dressing area.
  • 4 Bedrooms, Sleeps 8
  • Master Bedroom - 1 king , Views of Old Mill, ocean, harbor
    Yellow Room - 2 twin/ single , Views of ocean, trees, church steeples
    Green Room - 2 twin/ single , Views of trees
    Lower Level - 2 twin/ single , Well-lighted, above ground with own bathroom, entrance/exit
  • Three air-conditioned bedrooms of varying sizes are on the second floor, each with comforting views of nature and each is painted lovely, cheery colors. The fourth bedroom is in the well-lighted and well-ventilated, aboveground lower level, which has wall-to-wall carpeting, its own entrance/exit, a full bathroom, loveseat and large cable flat-screen TV. Bright Nantucket-themed pictures and wooden boat and framed knots cover the walls. Children vie with each other to stay in this cheery room.
  • Audio Tape Player
  • Books
  • Books for Adults
  • Books for Kids
  • CD Player
  • DVD Player
  • Games ...
  • Games for Kids
  • Radio
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Toys ...
  • VCR
  • Video Game Console
  • Video Games
  • Barbecue
  • Beach Chairs
  • Beach Towels
  • Beach Umbrellas
  • Binoculars
  • Large Cooler
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Porch / Veranda ...
  • Screen Porch / Veranda
  • Small Cooler
  • Unscreened Porch / Veranda
  • 8 garden chairs
  • 8 beach chairs
  • Long-term Renters Welcome
  • children welcome
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible
  • bay/sound
  • churches
  • cinemas
  • coin laundry
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • nude beach
  • playground
  • pond
  • restaurants
  • synagogues
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • sledding
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • hiking
  • hunting
  • hunting big game
  • hunting small game
  • ice skating
  • jet skiing
  • kayaking
  • paragliding
  • parasailing
  • pier fishing
  • racquetball
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
Homeowner has return boat tickets from Hyannis for guests' cars for August 2, August 9 and August 16. Superb location to all attractions in town and around the Island; wraparound porch, partially enclosed; four teak Adirondack chairs, three picnic tables and benches. Marvelous views of a quiet, historic working windmill (built in 1746) that grinds corn; off-street parking for two cars; complimentary Internet WiFi service; plump blackberries on long, winding driveway to pick for cooking or eating. Windswept sits on one of Nantucket's highest points with views no other Island home has of the windmill, the harbor, ocean, bay, the town's church steeples and small forests on two sides. Tall windows make Windswept a light-filled, comfortable home. Butterflies and rabbits scamper about in large front and backyards.

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