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Charming, Family Friendly Home Near Surfside Bike Path

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A wooden deck with lounge chairs and benches, surrounded by greenery.
A two-story wooden house with a dark shingled exterior, a front porch, and a small garden with hydrangeas and other plants.
A wooden dining table with chairs, a vase with dried flowers, and kitchen utensils on the counter.
A living room with a sofa, armchairs, a glass coffee table, a dining table with chairs, a lamp, and a mirror.
A bedroom with a bed, two bedside tables, a lamp, a door, and a wall-mounted picture.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Discover nearby landmarks
    Walk to The Old Mill

Popular amenities

  • Patio
  • Swimming pool
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Washing machine

Explore the area

View map
Nantucket, MA
  • Place, The Old Mill
    ‪13 min walk‬
  • Place, Nantucket Historical Association
    ‪16 min walk‬
  • Place, Nantucket Atheneum
    ‪4 min drive‬
  • Airport, Nantucket, MA (ACK-Nantucket Memorial)
    ‪11 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Garden
Dining area

Add dates for prices

Similar properties

Aerial view
TRANQUILITY IN NANTUCKET
Nantucket
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
10.0 out of 10, Exceptional, (29 reviews)
TRANQUILITY IN NANTUCKET

About the area

Nantucket

Located by the sea, this holiday home is in Nantucket Town, a neighbourhood in Nantucket. The area's natural beauty can be seen at Lily Pond Park and Sesachacha Heathlands Wildlife Sanctuary, while Nantucket Historical Association and Fire Hose Cart House are cultural highlights. Loines Observatory and Vestal St Observatory are also worth visiting. Kayaking and waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and hiking/biking trails nearby.
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Map
Nantucket, MA

What's nearby

  • The Old Mill - 13 min walk - 1.1 km
  • Nantucket Historical Association - 16 min walk - 1.4 km
  • Nantucket Atheneum - 4 min drive - 2.1 km
  • Quaker Meeting House - 4 min drive - 2.1 km
  • Children's Beach - 5 min drive - 2.5 km

Getting around

  • Nantucket, MA (ACK-Nantucket Memorial) - 7 min drive

Restaurants

  • ‪Handlebar Cafe - ‬4 min drive
  • ‪The Nantucket Lobster Trap - ‬3 min drive
  • ‪Lemon Press - ‬5 min drive
  • ‪The Club Car - ‬4 min drive
  • ‪45 Surfside - ‬8 min walk

Frequently asked questions

Does Charming, Family Friendly Home Near Surfside Bike Path have a pool?

Yes, this property has a pool.

How much does it cost to stay at Charming, Family Friendly Home Near Surfside Bike Path ?

As of 5 Nov 2026, prices found for a 1-night stay for 2 adults at Charming, Family Friendly Home Near Surfside Bike Path on 9 Nov 2026 start from AU$5,106, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Charming, Family Friendly Home Near Surfside Bike Path pet-friendly?

No, pets are not allowed at this property.

How much is parking at Charming, Family Friendly Home Near Surfside Bike Path ?

On-site parking is available at the property.

What time is check-in at Charming, Family Friendly Home Near Surfside Bike Path ?

Check-in begins at 4:00 PM.

What time is check-out at Charming, Family Friendly Home Near Surfside Bike Path ?

Checkout is at 10:00 AM.

Where is Charming, Family Friendly Home Near Surfside Bike Path located?

Located in Nantucket Town, this holiday home is within 1 mile (2 km) of The Old Mill, "Colored" Cemetery and Nantucket Historical Association. Hadwen House and Historic Mitchell House are also within 1 mile (2 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 8 out of 10 reviews
Rating 8 - Good. 2 out of 10 reviews
Rating 6 - Okay. 0 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Great house with plenty of room and a great backyard. Really enjoyed our stay and highly recommend the house to anyone visiting the island.
Stayed 2 nights in Sep 2023
Response from VrboOwner on 17 Oct 2023
Thank you, Kevin! So glad you enjoyed your stay at "Gail Winds,"and we'd be delighted to welcome you back!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very nice home in very nice neighborhood

Very nice and comfortable house in a great location.
Stayed 7 nights in Aug 2021
Response from VrboOwner on 16 Aug 2021
Thanks so much for your kind words and for taking such good care of "Gail Winds"! We hope to see you again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Getaway

Great location worked out really well!!
Stayed 2 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Charming Retreat

Everything was perfect for our stay, the home is adorable with plenty of space and quaint backyard. It’s a nice walk to town with some local shops nearby. Gail was very easy to work with, thank you!
Stayed 3 nights in Jun 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely neighborhood

Ages 6-71 enjoyed this property. Gail was extremely responsive and the back deck was lovely for dinners. It has a gas grill (most places we've stayed on in ACK have charcoal), so that was a nice plus! Convenient to the grocery store, walking distance to a playground. Don't miss the croissant bacon egg and cheese from Surfside (within walking distance too!)
Stayed 5 nights in Jun 2024
Response from VrboOwner on 8 July 2024
Thank you, Lizzie! We are so glad you enjoyed Gail Winds and especially the back deck. Come bACK soon!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Graduation weekend

We enjoyed our time on Nantucket and this rental was in a great location. The neighborhood is lovely and its proximity to everything is good. We did run into some things we had not expected. The deck was not prepared as shown in the web photos. We would have had to do much sweeping and wiping to use it. The interior had muck more incidental decor than we expected. Once we moved some and stored it the surfaces became more useable. We also paid a substantial cleaning fee for our stay and were greeted with a list of cleaning chores we were expected to perform prior to our 10AM check out.
Stayed 4 nights in Jun 2023
Verified review

8/10 Good

Cute spacious cottage providing all the basic necessities for you vacation

My first comment is that the owner of this house, Gail, is SUPER responsive and helpful. She explained everything and was very quick in replying to e-mails when we had questions. The house is spacious (though I live in a tiny house in the middle of a large city, so maybe its relative to whatever you're used to) and provides all basic necessities for a vacation in Nantucket (beach towels, patio with grill, outdoor shower, washer / dryer, all kitchen items, window air conditioning units etc). The location was great, we only had bicycles and most beaches and restaurants were easy to reach by the bike paths. There is a shuttle stop at the end of the street but we didn't use it. If you have kids this house is very close to the high school and my kids really enjoyed using the baseball diamond and basket ball nets there, very quick bike ride away. If you're looking for a moderately priced house in Nantucket in a great location this is a great option. My only comment on what could have made the week a little better would be if some of those beach chairs with the straps for carrying on your back had been available for use. We enjoyed our time here : )
Stayed 7 nights in Aug 2018
Response from VrboOwner on 20 May 2020
Thank you, Katie! It was a pleasure to have you and your family at "Gail Winds." And thank you for letting me know about the beach chairs. They tend to disappear over a summer, and I'll be sure to add them to the check list for the future.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay in Nantucket!

Gail's Wind was the perfect place to stay for a weekend trip with friends to Nantucket ! Such a cute spot - nice bedrooms and good common area for a group, great location and very easy check in/out process! Gail was able to accommodate our request for early check in. The only complaint was we ran out of toilet paper and paper towels and were unable to find refills in the home. Otherwise, wonderful stay and I would absolutely recommend for anyone visiting Nantucket!
Stayed 2 nights in Sep 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great home and loved the deck!

So helpful and a great stay!
Verified review

10/10 Excellent

Great location! The owner, Gail, was very responsive and easy to reach!

Quiet neighborhood setting, centrally located on the island made this home a great stay! Clean and charming home, with everything we needed for our getaway!
Stayed 7 nights in Jul 2018
Response from VrboOwner on 20 May 2020
Dear Tricia, I’m so glad you enjoyed your stay at our island home! Thank you for choosing to stay. We were so glad to have you and hope to welcome you back to “Gail Winds”!! Best, Gail
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