Nantucket Gem - Private Setting / Edge of Town/1 mile to beach and town
Welcome to the Windham House! This upside down vacation home is casual, comfortable, and is set on a very private, quiet lot with beautiful sunset views. The setting is truly wonderful and idilic, situated off a private dirt road.
The location provides easy access to everything that Nantucket has to offer! Getting around is convenient on foot, bike, car or bus. The home is adjacent to the Madaket Bike path and also close to the local bus (called “The Wave”). It is one mile to the historical downtown area filled with museums, galleries, shops and restaurants. The closest beach is 1.3 miles away (Steps Beach). If you love nature, there are many conservation areas to explore within walking distance. Our favorite for expansive ocean views is Tupancy Links.
The house is a great spot to access Nantucket’s shops and restaurants and is also great for relaxing and taking it slow. A typical day could involve walking to downtown for some shopping, getting sandwiches at Something Natural, choosing a beach for some sun and fun, and then unwinding at home on the upstairs deck to let the fresh ocean air recharge you. Grab a cocktail or a Cisco beer and sit and read your book all day. Bird lovers, keep a lookout for hawks and the many bird species that abound.
The home is an upside down house, which means the main living area is upstairs to take advantage of the setting. The first floor has two bedrooms each with twin beds, a full bathroom, laundry area, and a living room with two futons and a TV. The laundry area has beach towels for 6. Upstairs is the master bedroom with a queen bed, a full bathroom, the kitchen and dining area, living room, and an outdoor deck with seating to enjoy the wonderful scenery. The side deck features a charcoal bbq. The yard is private with plenty of parking and room to have fun and play. Use the outdoor shower and shed with beach chairs and toys. The home is also equipped with a pack-and-play and baby gates for families traveling with children.
We look forward to hosting you at our Nantucket home! Please reach out with any questions.
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Due to the short season, in the summer months weekly rentals only. Saturday to Saturday. June-September
Important information
You need to know
Property Registration Number C0211701970
Property # 1694258vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
About the area
Nantucket
Located near the beach, this holiday home is in Nantucket Town, a neighbourhood in Nantucket. Nantucket Ferry Terminal and Cisco Brewers are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Lily Pond Park and Smith's Point Wildlife Sanctuary. Loines Observatory and Vestal St Observatory are also worth visiting.
Nantucket Historical Association - 16 min walk - 1.4 km
First Congregational Church - 3 min drive - 1.8 km
Nantucket Atheneum - 3 min drive - 1.8 km
Whaling Museum - 3 min drive - 1.8 km
Children's Beach - 4 min drive - 2.2 km
Getting around
Nantucket, MA (ACK-Nantucket Memorial) - 10 min drive
Restaurants
Brotherhood of Thieves - 4 min drive
Stubbys - 4 min drive
Island Coffee - 4 min drive
Lemon Press - 4 min drive
Something Natural - 19 min walk
Frequently asked questions
Is Nantucket Gem - Private Setting / Edge of Town/1 mile to beach and town pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Nantucket Gem - Private Setting / Edge of Town/1 mile to beach and town?
As of 12 May, 2026, prices found for a 1-night stay for 2 adults at Nantucket Gem - Private Setting / Edge of Town/1 mile to beach and town on 3 Oct, 2026 start from S$800, 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.
How much is parking at Nantucket Gem - Private Setting / Edge of Town/1 mile to beach and town?
On-site parking is available at the property.
What time is check-in at Nantucket Gem - Private Setting / Edge of Town/1 mile to beach and town?
Check-in begins at 3:00 PM.
What time is check-out at Nantucket Gem - Private Setting / Edge of Town/1 mile to beach and town?
Checkout is at 10:00 AM.
Where is Nantucket Gem - Private Setting / Edge of Town/1 mile to beach and town located?
Located in Nantucket Town, this holiday home is within 1 mile (2 km) of Lily Pond Park, Jethro Coffin House and Old Gaol. Loines Observatory and Fire Hose Cart House are also within 1 mile (2 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Beautiful place! Very thoughtfully appointed with everything you need. Host was EXCEPTIONALLY prompt in responding to any questions and was perfectly helpful!
We thoroughly enjoyed our recent stay. The home was comfortable and well equipped, and located a short drive from town. It was also nice that it was on a dead end road, and very quiet. We would certainly stay here again!
Jason R.
Stayed 4 nights in Oct 2024
Response from VrboOwner on 19 Oct, 2024
Thank you for the lovely review! We are glad you enjoyed your stay and hope to host you again soon.
We loved our stay in Nantucket! The house was super clean and was a great location close to town and a number of beaches. Kirsten was an amazing host and made it a seamless booking experience and gave great insight about the island. I would recommend this spot to any family.
Kirsten's house was perfect for our long weekend getaway! It's nestled in a beautiful, quiet neighborhood but is only a 20 minute (very enjoyable) walk to town, which we did daily. We rented a car for the stay which was useful for getting to Steps beach, Cisco, etc. The house was clean, spacious and had everything we needed (beach towels, shower towels, beach chairs, etc.). Kirsten was a super responsive, kind host. I will definitely be going back!
Jackie M.
Stayed 3 nights in Sep 2024
Response from VrboOwner on 11 Sept, 2024
Thank you for the very kind review! It was a pleasure hosting your group and we look forward hosting you again the future.
We loved staying at this wonderful property! It was far enough outside of town to provide a sense of peace and quiet, while close enough to easily bike into town for shopping, dining, or ice cream. Surfside, Madaket, Steps, and Cisco beaches are all a relatively easy bike ride away. The layout was great b/c it allowed my teenage daughters to have their own space on the first floor, while the master was on the second floor. And the upside down style of the house allowed so much light in the sitting room, dining area and kitchen - I loved sitting out on the porch watching the bunnies in the yard! We will definitely be back!
Stacy T.
Stayed 7 nights in Jul 2025
Response from VrboOwner on 15 Jul, 2025
Thank you for the wonderful feedback Stacy. We really enjoyed hosting you!!
We really enjoyed our stay at this lovely home. Great space for our family of 4. Location was perfect for us…so close to town yet in private, quiet area. Great walking path right by the house and steps beach is only 5 minutes away. On the interior, the house has a great layout with living space/kitchen/dining on the 2nd floor and pretty view out of the French doors which lead to a deck. Also, I enjoy cooking and found the kitchen to be much better equipped for cooking than many other rentals I have stayed in. Highly recommend!
Melissa G.
Stayed 14 nights in Jun 2022
Response from VrboOwner on 31 Jul, 2022
Hi Melissa- Thank you for the wonderful review! We are so glad you enjoyed your stay. It was great hosting you. Come again soon!!
This home is wonderful! Then location is ideal. With easy access to town (by bike, car or even walking), steps beach, out to madaket, to mid island, etc. the property is well kept making it great for hanging outside on the upstairs deck, front porch or even on the lawn. The home is well stocked with comfortable and stylish furnishing. It feels like a home, not a rental meaning that it’s actually comfortable to hang out in.
We stayed here for a week in late August and it was by far our favorite rental house out of many years of coming to Nantucket! We are a family of five with three school aged children and the house was ideal in every way. The location is close to town and convenient to everything mid-island, but also very quiet and private with a great yard for the kids to enjoy. We enjoyed being right on the madaket bike path, and it was an easy bike ride to many places on the island, even for our youngest child.
The house itself had everything you could need, including great air conditioning, comfortable beds, plenty of towels, and a great washer & dryer. Many homes on the island have a bit of a damp feeling, especially on the ground floor, but this house was dry and clean throughout both floors. We would absolutely stay here again - it was a perfect place for our family!
Sarah B.
Stayed 7 nights in Aug 2024
Response from VrboOwner on 11 Nov, 2024
Wow, what a lovely review. It’s wonderful that you had such a nice trip! Thank you so much for staying with us. We hope to host you again soon.
Just spent the dreamiest week in Nantucket with my husband and parents! We all couldn't get over the house - photos do not do it justice. This is the cleanest, most well-cared for rental I have ever stayed in and the natural light was unbelievable. We enjoyed many coffees and cocktails on the beautiful deck, enjoying gorgeous sunsets and peace + quiet.
The location could not be better! We walked to town at least once per day, and our favorite South Shore beaches were a mere 10 minute drive. We explored the whole island easily from this launch point.
And finally, communication with Kirsten was wonderful. She answered questions quickly and was accomodating on our requests - although there weren't many, as the house is fully stocked with everything you need!
A dream stay and we will return!
Natalie H.
Stayed 7 nights in Jun 2023
Response from VrboOwner on 8 Sept, 2023
Thank you for such a kind review and for being great guests! We hope to host you again!
We have stayed at many homes on the island, but we especially enjoyed our stay here. It is in a very central location and it was easy to get around the entire island. We highly recommend this property.
If you’re looking for a well-maintained home, beautiful grounds, all amenities, plenty of beds, a responsive owner, and proximity to pretty much everywhere on the island, this is your place!
The grounds/landscaping were so beautiful. There is a shed that has beach chairs, umbrellas, and toys so you don’t have to bring your own.
The house was spotlessly clean and well-appointed with plenty of linens, kitchen items, and paper goods.
The only issue we had with cleanliness was that the prior renters must have stored fish in the freezer because it positively reeked when we got there. I contacted the owner and she got back to me right away and sent over the housekeepers, who cleaned the fridge and freezer and this helped with the smell. It was certainly not a deal-breaker (ie we were still able to use the fridge/freezer) and we were happy with the quick response.
My kids loved the “upside down” aspect of the house but were a little scared sleeping on the first floor by themselves. So just keep that in mind if you have young kids—the master is upstairs and there are 4 twins and 2 futons downstairs. They ended up being so exhausted after some fun days on Nantucket that they fell asleep fast and didn’t care where they were. :)
Every time we left the house to go somewhere, the GPS read 7-11 minutes. In other words, this house is in a great location. Right outside town (you could probably walk as it’s only 2 miles, but the sidewalk situation isn’t great), 7 minutes from a grocery store and gas station, and very close to Jetties Beach (again, not easily walkable, but a quick drive).
This was my first VRBO and it went so well. I would definitely rent this house again!
Kathleen M.
Stayed 4 nights in Oct 2021
Response from VrboOwner on 17 Oct, 2021
What a lovely review! Thank you for the kind words and for being wonderful guests. We are so happy you enjoyed your stay with your family. Come back soon!
We enjoyed our stay at this beautiful home. This is a very clean and stylish house, with everything you need. Beautiful and private landscaped property. The host was pleasant and available and very helpful with any questions. Thank you for a wonderful stay.
Robert M.
Stayed 14 nights in Sep 2021
Response from VrboOwner on 17 Oct, 2021
Thank you so much for the kind review. We are so happy to hear that you enjoyed your stay on the island of Nantucket! You are welcome back anytime.
House was perfect for our needs. Close to town and clean. Pictures don’t do it justice. Owner was very easy to communicate with and accommodating. Would rent again!
Susan C.
Stayed 6 nights in Oct 2020
Response from VrboOwner on 12 Oct, 2020
Thank you for the kind words Susan. Itwas a pleasure having you. We hope to host you again soon! Best, Kirsten
Our family has owned this home for over 30 years and have spent many vacations on the beautiful island of Nantucket. We hope that this house will bring you joy and help you create family memories like it has for us. We welcome you to our home.