Featured Fall Rentals on Nantucket
There’s something special about Nantucket in the fall. As the pace of summer begins to slow, the island settles into a quieter season filled with crisp mornings, uncrowded beaches, beautiful light, and plenty of time to enjoy everything Nantucket has to offer.
September and October are ideal months for an island getaway. Spend the morning walking the beach, explore Nantucket’s miles of bike paths and conservation trails, wander through Town or ’Sconset, and end the day with a sunset along the west end. With fewer crowds and cooler temperatures, fall offers a chance to experience a different side of the island.
The Rental Agents at Fisher Real Estate have curated a selection of homes still available for fall stays, whether you’re planning a long weekend, a week away, or a spontaneous escape to Nantucket.
Explore our featured fall rentals below and find the perfect place to settle in for the season.
Ready to plan your fall getaway? Contact the Fisher Real Estate rental team for availability and personalized assistance finding the right Nantucket home.
70 Vestal St
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Fisher Agent: J. Brent Tartamella
Weekly Rental Rate: $25,000
Dates: 8/28-9/04/2026
Tucked away on a quiet street and surrounded by lush landscape, this spacious five-bedroom home offers privacy and space to spread out, yet is only a mile from Main Street. Enjoy both indoor and outdoor living spaces including a pool, beautiful patio area, and multiple decks.
One Ocean Avenue
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Fisher Agent: Jen Shalley Allen
Weekly Rental Rate: $35,000
Dates: 8/15-9/30/2026
Completely refurnished in 2026, this iconic home is located in the heart of Sconset and is convenient to the village as well as the beach. It features a main house and a very cool recreation bar for movie watching and game playing. There are also two additional guest structures.
23A Union Street
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Fisher Agent: Lara Hanson
Weekly Rental Rate: $15,500 – $20,000
Dates: 8/23-8/29/2026 After 9/20/2026
23A Union Street is a spacious five bedroom, five- and one-half bath home that has been renovated with the highest attention to detail. Offering three floors of living space, the property boasts beautiful antique wide pine floors, central air, high end kitchen appliances and many custom built-ins. Just moments from Main Street, heading into the heart of town to enjoy shopping, dining, and historic sites is a breeze. There is also a driveway with one parking space which is a bonus for an in-town property.
8 Heath Lane
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Fisher Agent: Liza Hatton
Weekly Rental Rate: $10,000
Dates: September 16th onward
8 Heath Lane is a private vacation home, which sleeps up to 12, and is located at the end of a quiet lane in Tom Nevers East, under two miles from Sconset Village and just one and a half miles to Tom Nevers beach access. A new 15 by 32 foot heated salt water pool with stone deck surround and teak chaise lounges add to existing outdoor living spaces, including two decks, a stone patio with fire pit and lighted pergola perfect for al fresco dining. It abuts 28 acres of Land Bank property and has second-floor views all the way out to Sankaty Lighthouse. In addition, the home is part of the Tom Nevers East HOA and you have access to the nearby community tennis courts. The interior in newly refinished, including fresh paint and new furnishings. Pets are welcome here. The yard is fenced in, and there are food/water dishes, a jar of treats, and an extra-large dog crate for use if needed. The driveway is large with ample parking.
49 Warrens Landing Road
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Fisher Agent: Gina O’Callaghan
Weekly Rental Rate: $6,800
Dates: After 9/12/2026 (3 or 4 night minimums through end of October)
This beach chic cottage offers privacy and simplicity to ensure an incredible summer vacation. Upon approach, down a long private drive, you find this one story cottage with a large expansive lawn for summer games and at the back of the home, the harbor facing deck invites you to relax and take in the gorgeous views.
5 Village Way
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Fisher Agent: Jen Shalley Allen
Weekly Rental Rate: $35,000
Dates: 9/7-10/31/2026
Come for the views, stay for the scallops! This is the perfect fall retreat in which to enjoy front row views and direct access to the harbor. Recreational scalloping begins October 1st.
1 Jonathan Way
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Fisher Agent: J. Brent Tartamella
Weekly Rental Rate: $10,500
Dates: 9/05-9/12/2026
A quick and discounted escape to the island at one of the most loveliest times of year. A retreat to unwind and relax during one of the best weeks of the year. Unwind poolside, head down to the beach or drive in to town as the kids are all back to school.
7 Comeau Lane
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Fisher Agent: Liza Hatton
Weekly Rental Rate: $9,000 – $12,500
Dates: 8/30/2026 onward
Situated on a quiet ‘Sconset lane, this home is immaculately designed and decorated. Every detail of this four-bedroom home is thoughtfully executed. The home seamlessly flows from interior to exterior with impressive great rooms and intimate spaces. The outdoor area has a patio with outdoor furniture, a garden, an outdoor shower and beautiful landscaping. It is 2/3 of a mile to ‘Sconset Village, where you will find restaurants, a café, market, liquor store and beach access.
63 Monomoy Road
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Fisher Agent: J. Brent Tartamella
Weekly Rental Rate: $10,500
Dates: 9/15-10/17/2026
Tucked at the end of prestigious Monomoy Road on a private drive, this four-bedroom retreat opens to sweeping views across the moors and island sunsets over Nantucket Harbor. Wrap-around mahogany and cedar decks, cathedral ceilings, and an unusually large, screened yard make it as easy to host a crowd as it is to disappear with a book for the afternoon. Monomoy’s calm harbor beach is a couple hundred yards from the door and town is minutes away – private, but never remote.
15 Sconset Avenue
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Fisher Agent: Liza Hatton
Weekly Rental Rate: $6,000
Dates: September 7th onward
This charming Sconset home is situated on a quiet road with a well-manicured yard on a corner lot. There is a wrap-around porch and brick patio to enjoy the beautiful summer days as well as an outdoor shower for rinsing off after the beach. The house is situated about ¾ mi to Sconset Village, where you can find restaurants, a market, a liquor store, post office, a playground and beach access. Bike paths are close by and the NRTA bus leaves Sconset twice an hour all summer long.
9 Bluebird Lane
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Fisher Agent: Gina O’Callaghan
Weekly Rental Rate: $9,100
Dates: After 9/06/ – 10/02/2026 (4 night minimums – price shown is for a 7 night stay)
Fresh and airy, this pet friendly large rental home is located in the Naushop neighborhood, offering a pool and tennis courts, minutes to south shore beaches, 2 miles to town and easy access to the bike paths around the island along with the Wave transit system. If Naushop is on your radar, this new-to-the-rental-market home should not be overlooked, especially considering dogs are allowed! Sleeping capacity up to 12 on three floors of living.
74 Main Street
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Fisher Agent: Liza Hatton
Weekly Rental Rate: $18,000
Dates: 08/29 – 09/06, after 09/25/2026
Located at the top of Main Street Nantucket, in the charming historic district, this historic five bedroom home not only offers a convenient and wonderful location to access Town but boasts wonderful and private outdoor areas. The spacious back deck has dining for ten guests, a gas BBQ, sun loungers and an outdoor shower. This house is impeccably maintained and has two off street parking spots for tenants.
31 Flintlock Road
Link to Rental
Fisher Agent: Liza Hatton
Weekly Rental Rate: $15,000
Dates: After 09/05/2026
Thoughtfully reimagined, Longtail Cottage is a private retreat with sweeping views toward the Atlantic Ocean and Sankaty Lighthouse. The classic upside-down layout maximizes light and scenery. The home offers exceptional privacy, beautifully appointed interiors, and tranquil spaces that seamlessly blend indoor and outdoor living. The outdoor space is designed as an extension of the home’s interiors. It invites guests to embrace Nantucket’s coastal lifestyle. Three distinct spaces offer secluded settings for dining, lounging, and entertaining. The pool terrace serves as a private resort-style retreat, featuring four cushioned chaise lounges, an outdoor living room, and a fire pit framed by a generous sectional. The primary suite’s secluded balcony provides an intimate escape overlooking the heated pool, while the upper dining terrace captures expansive views across the Atlantic Ocean and Sankaty Lighthouse. Furnished with seating for six and a premium gas grill, it offers an unforgettable setting for leisurely meals, sunset cocktails, and evenings spent outdoors, where the boundaries between the home’s interior and the natural beauty beyond quietly disappear.
