Section I · The Ranked Twelve
From best to twelfth.
Sorted by what each house actually does well at its price point, on the peak July week.
No. I
3 Fintry Lane, Dionis (Fisher Real Estate).
Bedrooms: 8. Sleeps: 16. Neighborhood: Dionis, north shore. Beach access: 4-minute walk to private beach path. Peak weekly rate: $38,500 / wk peak summer (June 27 to July 4, July 11 to 18, August 22 to 29, 2026), verified on fishernantucket.com (May 2026). Included: heated pool, hot tub, gas grills, beach gear locker, four bicycles, weekly mid-stay housekeeping. Not included: chef, daily housekeeping, beach attendant.
Why it ranks here: Eight king bedrooms with 8.5 bathrooms is the configuration that makes a 16-person Nantucket trip work without bunk rooms. The Dionis side holds the calmest water on the island (the cove is glass when the south side is breaking 3 feet), and the private beach path saves the 20-minute walk that Cisco-side properties demand. The kitchen handles a full-occupancy sit-down for 16. We stayed in this property in July 2024.
What we would change: the north-shore positioning means morning fog is more frequent than south-shore. Build outdoor plans around afternoon, not morning, in the first two weeks of July.
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No. II
Six-bedroom main with two-bedroom cottage, Sconset bluff.
Bedrooms: 8 (6 main, 2 cottage). Sleeps: 16. Neighborhood: Sconset bluff, east end. Beach access: 90-meter walk down the bluff stairs to Sconset Beach. Peak weekly rate: $32,000 to $67,700 / wk (July 25 to August 1, August 8 to 15, 2026), verified through Fisher Real Estate listing inventory (May 2026). Included: heated pool, spa, separate cottage with full kitchen, beach gear, six bicycles. Not included: chef, beach attendant, daily housekeeping. .
Why it ranks here: Sconset is the village that holds the rose-covered cottage register and the only east-facing sunrise beach on the island. The two-bedroom cottage solves the multi-generational separation problem: parents and grandparents in the main, in-law unit independent for the week. The bluff walk is real (44 steps) and not gentle. Confirm anyone in the party can manage it before booking.
What we would change: the bluff erosion conversation matters. Three Sconset bluff houses moved inland in the 2018 to 2024 window. Confirm the property’s elevation and the bluff-foot distance with the manager on inquiry.
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No. III
Eight-bedroom oceanfront, Cisco.
Bedrooms: 8. Sleeps: 16. Neighborhood: Cisco, south shore. Beach access: private path direct to Cisco Beach (30-meter walk). Peak weekly rate: $68,000 to $96,000 / wk peak July, listed across Compass and Great Point Properties as of May 2026. Included: heated pool, hot tub, full beach setup with attendant for the first three days, gas grills, eight bicycles. Not included: chef (mandatory at $1,800 per day for 14+), daily housekeeping. .
Why it ranks here: direct oceanfront on Cisco is the rarest configuration on the south shore. Most “oceanfront” Cisco properties sit across Hummock Pond Road. This one does not. The path to the sand is shorter than the walk from most Sconset bluff properties. Eight kings, a kitchen built for catered service, and the only south-shore property on this list that holds the full 16-person occupancy without compromise.
What we would change: south-shore wave action is real. Cisco breaks 3 to 5 feet most July afternoons. If anyone in the party expects flat-water swimming, base in Dionis or Pocomo instead.
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No. IV
Seven-bedroom main and guest house, Quidnet.
Bedrooms: 7. Sleeps: 14. Neighborhood: Quidnet, mid-island north. Beach access: private dock on Sesachacha Pond, 10-minute drive to Quidnet Beach. Peak weekly rate: $42,000 to $58,000 / wk peak. Included: pool, hot tub, kayaks and paddleboards on the pond, gas grills, six bicycles. Not included: chef, daily housekeeping, beach attendant. .
Why it ranks here: Quidnet is the under-rented pocket. The pond gives a calm-water option for children and a separate sunset frame. Sesachacha Pond is one of the two Nantucket great ponds open to the Atlantic on a controlled cycle (the harbormaster opens the cut in spring and fall). The drive to Town is 12 minutes, to Sconset 6 minutes, to Quidnet Beach 4 minutes. Right for a group that wants the village without paying the Sconset or Cisco bluff premium.
What we would change: mosquito-and-greenhead season runs the last week of June through the third week of July. The screened porch matters here. Ask the manager about exterior pest control in writing on inquiry.
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No. V
Five-bedroom Town historic, Cliff Road.
Bedrooms: 5. Sleeps: 10. Neighborhood: Cliff Road, Town. Beach access: 6-minute walk to Steps Beach. Peak weekly rate: $28,000 to $42,000 / wk peak, with Historic District Commission compliance on the exterior fit-out. Included: small heated plunge pool, garden, gas grill, four bicycles. Not included: chef, daily housekeeping, ocean-frontage. .
Why it ranks here: the in-town value pick. Walking distance to Main Street (8 minutes), the Whaling Museum, and the morning bakery line at Something Natural. The Historic District Commission keeps the streetscape consistent (cedar shake, white trim, three-quarter Cape proportion), which means this register holds its visual identity in a way no new-construction property does. Five proper kings, a kitchen built around a 10-person sit-down, and the Steps Beach access that the Town address gives.
What we would change: the in-town parking is two spaces. For a 10-person group with two or three cars and a kitchen-supply Stop & Shop run, plan to use the curbside permit. Confirm permit issuance on inquiry.
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No. VI
Six-bedroom Pocomo waterfront with dock.
Bedrooms: 6. Sleeps: 12. Neighborhood: Pocomo, mid-island north on the harbor. Beach access: private harbor dock and beach (130-meter frontage). Peak weekly rate: $48,000 to $72,000 / wk peak. Included: heated pool, hot tub, harbor dock with two slips, kayaks and paddleboards, gas grills, six bicycles. Not included: chef, slip electric and water (metered), daily housekeeping. .
Why it ranks here: the dock is the differentiator. Pocomo holds the calmest harbor water (north of Quaise) and a private slip lets the group bring or charter a boat that is at the house, not at the Town wharf. The drive to Town is 14 minutes; the boat ride into the harbor is 22 minutes at displacement speed. Six proper kings, a kitchen that holds a catered service for 12, and the harbor-side sunset that south-shore properties do not have.
What we would change: the dock requires a boat to actually use. If the group is not chartering, this property is paying for an amenity it will not use. Drop one rank in that case.
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No. VII
Seven-bedroom Tom Nevers oceanfront.
Bedrooms: 7. Sleeps: 14. Neighborhood: Tom Nevers, south-east. Beach access: private path to Tom Nevers Beach (40-meter walk). Peak weekly rate: $38,000 to $55,000 / wk peak. Included: pool, hot tub, beach setup, gas grills, six bicycles. Not included: chef, daily housekeeping, beach attendant. .
Why it ranks here: Tom Nevers is the south-east pocket between Sconset and the airport. The beach is empty by Cisco standards (the south-east is not a surf destination), and the drive to Sconset Market is 5 minutes. Seven proper bedrooms, kitchen built for the full occupancy, and the Tom Nevers Field park behind the property for children-friendly outdoor space. Right for a family-led group of 12 to 14 that wants the south shore without the Cisco crowd density.
What we would change: the drive to Town is 18 minutes. For a group that plans frequent in-town dinners (Lola 41, Dune, Cru), the cab math runs $50 to $80 each way. Add a driver-for-the-week line if the group plans more than three in-town dinners.
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No. VIII
Sconset four-bedroom cottage in the rose-covered core.
Bedrooms: 4. Sleeps: 8. Neighborhood: Sconset village core. Beach access: 6-minute walk via the bluff stairs to Sconset Beach. Peak weekly rate: $17,500 to $26,000 / wk peak (Sconset cottage band as listed on Fisher Real Estate, May 2026 verified). Included: small garden, outdoor shower, gas grill, four bicycles. Not included: pool, chef, daily housekeeping. .
Why it ranks here: the small-group entry point on the Sconset side. Walking to Claudette’s for sandwiches, walking to Chanticleer for the rose-arbor lunch (book six weeks ahead), and walking to the post office means the trip runs without a car for two of the seven days. Right for a four-person couple group or a six-person family with two small children.
What we would change: no pool. For July afternoons when the beach gives out, the inland heat without a pool option is the constraint. If anyone in the party tires on beach days, drop to a property with one.
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No. IX
Five-bedroom Madaket sunset-side.
Bedrooms: 5. Sleeps: 10. Neighborhood: Madaket, west end. Beach access: 4-minute walk to Madaket Beach. Peak weekly rate: $22,000 to $32,000 / wk peak. Included: outdoor shower, gas grill, four bicycles, beach setup. Not included: pool, chef, daily housekeeping. .
Why it ranks here: Madaket holds the only west-facing beach on the island, which means the only sunset bonfire spot inside Nantucket town limits. The Westender bar at Millie’s is the social anchor (the second tier to Galley Beach on the Town side). For a group that values the sunset more than the morning swim, Madaket is the right base.
What we would change: Madaket is 11 kilometers from Town and the drive is 22 to 28 minutes in summer traffic. Plan around the distance, not against it. Two in-town dinners a week, not five.
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No. X
Six-bedroom Polpis with harbor view.
Bedrooms: 6. Sleeps: 12. Neighborhood: Polpis, mid-island. Beach access: 8-minute drive to Quidnet or Sconset; harbor view from the upper deck. Peak weekly rate: $26,000 to $38,000 / wk peak. Included: heated pool, hot tub, gas grills, six bicycles. Not included: chef, daily housekeeping, direct beach access. .
Why it ranks here: the harbor view from Polpis without the harbor frontage premium. The drive to Town is 9 minutes via Polpis Road, to Sconset 8 minutes, and the property sits high enough that the upper-deck harbor view holds the visual register of a Pocomo or Wauwinet property at roughly half the rate. Six bedrooms, a kitchen built for the full group, and the price-to-square-footage math.
What we would change: the drive to any beach is the trade. Build the trip around beach-day-into-pool-afternoon rather than beach-walk mornings.
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No. XI
Five-bedroom Wauwinet north-shore.
Bedrooms: 5. Sleeps: 10. Neighborhood: Wauwinet, north-east tip. Beach access: private path to the Wauwinet beach (40-meter walk), with calm-water Bay side and ocean side at 20-meter separation. Peak weekly rate: $32,000 to $46,000 / wk peak. Included: heated pool, hot tub, kayaks, gas grills, four bicycles. Not included: chef, daily housekeeping, access to Wauwinet inn amenities. .
Why it ranks here: Wauwinet is the rare Nantucket pocket where bay-side and ocean-side beach are walkable from the same property (the spit narrows to 60 meters at the tip). For a 10-person group with both swimmers and surfers, the configuration matters. The Wauwinet inn (Topper’s restaurant) is a 6-minute walk for a single dinner reservation, not a base for the trip.
What we would change: the drive to Town is 18 minutes and to Sconset 14 minutes. The Wauwinet positioning is the trade-off here. For groups that want easy in-town nights, drop one rank.
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No. XII
Four-bedroom Surfside walking to the beach.
Bedrooms: 4. Sleeps: 8. Neighborhood: Surfside, south shore. Beach access: 8-minute walk to Surfside Beach. Peak weekly rate: $15,000 to $24,000 / wk peak, the only entry on this list below $25,000. Included: outdoor shower, gas grill, four bicycles, beach gear. Not included: pool, chef, daily housekeeping. .
Why it ranks here: Surfside is the high-traffic south-shore beach with the bike-path connection to Town (5 km on the Surfside Bike Path, 18 minutes by bike). The four-bedroom configuration works for an eight-person young-family or couple-led group on a $15,000 to $24,000 week. The Surfside Beach Shack handles the in-day food problem (sandwiches, lobster rolls, no reservations). Right for the group that wants Nantucket inside the $25,000-per-week ceiling.
What we would change: Surfside crowds in the peak week. The 11 a.m. lot is full by 9:30 most July Saturdays. Plan beach mornings, not afternoons.
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