Section I · The Ranked Fourteen
From best to fourteenth.
Sorted by what each villa actually does well at its price point. The number-one villa is the one we would book first given a free pick from all fourteen.
No. I
The Chilmark seven-bedroom waterfront, Stonewall Beach side.
Bedrooms: 7. Sleeps: 14. Town: Chilmark. Peak rate: $37,500 to $65,000 / week. Included: housekeeper, gardener, weekly bed-linen and towel change, heated pool and spa, two beach passes, association beach-key to Lucy Vincent. Not included: chef, daily housekeeping, transfer to and from the Vineyard Haven ferry.
Why it ranks here: the Stonewall Beach side of Chilmark holds the strongest combination of cliff position, walking distance to a private association beach, and shingled-Cape architecture on the island. The 2024 refit brought every bathroom to the same standard and replaced the kitchen island for serious cooking at 14. The owner has run the property under one management since 2017. Pool is heated through October. Acquisition of the Lucy Vincent association key on inquiry is the structural advantage; without it the property is materially less interesting. We have stayed in this villa twice, the most recent visit in August 2025.
What we would change: Wi-Fi at the guest annexe is slow. The owner has been told. The walk from the lower garage to the kitchen is 90 meters; for groups arriving with serious provisioning, ask the manager to use the upper service-vehicle gate instead.
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No. II
The Edgartown in-town six-bedroom, North Water Street.
Bedrooms: 6. Sleeps: 12. Town: Edgartown. Peak rate: $30,000 to $45,000 / week. Included: daily housekeeping, weekly linen and towel change, two cars, harbor-view balcony from three of the bedrooms. Not included: chef, pool (no pool on the property), beach service.
Why it ranks here: the in-town Edgartown six-bedroom is the only property on the editorial list that is walking distance to the Edgartown harbour, the Atlantic and the Chappy Ferry without a car. The 1893 captain’s house on North Water Street was refurbished to a standard the in-town inventory rarely reaches. Six proper en-suite bedrooms, three with harbor views. Walking distance to the Edgartown Yacht Club, Atria, the Newes from America, and the daily Chappy Ferry crossing to Chappaquiddick. No pool is the constraint; a buyer who needs a pool should rank the Chilmark and Katama options higher. We have stayed in this villa once, in July 2024.
What we would change: the second-floor master AC unit runs loud through the night. Replace before peak.
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No. III
The Aquinnah six-bedroom, Lobsterville-side bluff.
Bedrooms: 6. Sleeps: 12. Town: Aquinnah. Peak rate: $28,000 to $44,000 / week. Included: housekeeper, gardener, association beach pass to Lobsterville. Not included: chef, pool maintenance during the off-season, additional cars.
Why it ranks here: the Lobsterville bluff position holds the sunset over Vineyard Sound that the rest of the island does not. Six bedrooms, three of them with the same view, an infinity pool overlooking the bluff, and a kitchen that handles 12 at dinner without crowding the island. The walk to Lobsterville is six minutes downhill on a path the association maintains. The drive to the Aquinnah Cliffs viewing platform is four minutes. The trade-off is the cross-island distance: 28 minutes to Edgartown, 18 minutes to Chilmark Center, 35 minutes to the Vineyard Haven ferry on a Sunday afternoon in August.
What we would change: the lower-terrace shower stall floor drains slowly; address before peak.
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No. IV
The West Tisbury six-bedroom, Lambert’s Cove farm.
Bedrooms: 6. Sleeps: 12. Town: West Tisbury. Peak rate: $26,000 to $40,000 / week. Included: housekeeping twice a week, gardener, Lambert’s Cove beach sticker, vegetable-garden access, working barn. Not included: chef, pool (no pool, beach is the swim), daily housekeeping.
Why it ranks here: the Lambert’s Cove farm property is the only working-farm villa on our editorial list. The 14-acre plot holds two converted barns, the main farmhouse, and a vegetable garden that the housekeeping team picks from for the kitchen. Six bedrooms across the main house with no shared walls between the master and the kid rooms. The Lambert’s Cove beach sticker is the structural advantage; the beach is the calmest north-shore swim on the island and the sticker is restricted to West Tisbury residents and verified renters. No pool is the constraint; this is a beach-swim trip.
What we would change: the upstairs bathroom plumbing is original. Two reader emails on file describing morning hot-water lag.
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No. V
The Katama five-bedroom, South Beach side.
Bedrooms: 5. Sleeps: 10. Town: Edgartown (Katama). Peak rate: $24,000 to $36,000 / week. Included: heated pool, daily housekeeping, two cars, South Beach parking decal. Not included: chef, beach-cabana service.
Why it ranks here: the Katama-South Beach side of Edgartown is the family workhorse pocket on the island. This property holds a 14-meter heated pool, five king bedrooms with full en-suites, a properly equipped kitchen, and the South Beach parking decal that resolves the single biggest operational headache of a Katama week (the Norton Point access on a July weekend). The bike path runs by the front gate. Distance to Edgartown center is six minutes by car, 25 minutes by bike. We have not stayed in this villa; the August 2025 site visit and three repeat-guest interviews carry the assessment.
What we would change: the pool surround is brick laid in the 1990s and is uneven. Watch the children around the deep end.
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No. VI
The Vineyard Haven five-bedroom, West Chop ridge.
Bedrooms: 5. Sleeps: 10. Town: Tisbury (Vineyard Haven, West Chop). Peak rate: $22,000 to $33,000 / week. Included: housekeeping twice a week, West Chop Club guest pass (limited), gardener. Not included: chef, pool, club membership transfer.
Why it ranks here: the West Chop ridge is the closest editorial-list pocket to the Vineyard Haven ferry (six minutes by car) and the lowest-friction pocket for short-week arrivals. The 1922 shingled house was refurbished in 2023 with the original lines kept. Five bedrooms, two with sound views, ferry signal across the dining table at sunset. Walking access to Tashmoo Beach for the kayak program. The West Chop Club guest pass is restricted to two arrivals and not transferable; verify before paying the deposit.
What we would change: the second-floor hallway floor is original pine and squeaks loud enough to wake the master.
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No. VII
The Chilmark six-bedroom, Menemsha Pond.
Bedrooms: 6. Sleeps: 12. Town: Chilmark. Peak rate: $28,000 to $44,000 / week. Included: heated pool, dock with private boat slip for a vessel under 24 feet, housekeeper, kayak inventory. Not included: chef, larger-vessel mooring, daily housekeeping.
Why it ranks here: the Menemsha Pond property is the boating pick on the list. A private slip for a vessel under 24 feet (a typical Boston Whaler or center-console day boat), pond access for kayak and paddleboard, and direct walking distance to the Menemsha working harbor for the fish-buy and the Larsen’s lobster line. Six bedrooms across the main house plus a separate one-bedroom guest cottage that is rentable on inquiry. The pond is brackish and the swim is fine but the trip is more about the boat program than the water itself.
What we would change: the cottage shower has poor water pressure. Two reader emails on file.
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No. VIII
The Edgartown four-bedroom, harbor view.
Bedrooms: 4. Sleeps: 8. Town: Edgartown. Peak rate: $20,000 to $30,000 / week. Included: heated pool, daily housekeeping, one car, harbor-view from the dining room and pool deck. Not included: chef, second car, beach-cabana service.
Why it ranks here: the small-group pick on the list. Four king bedrooms, three of them with harbor views, a 10-meter pool, a dining room that holds eight comfortably, and a 12-minute walk to the Edgartown harbor restaurants. The right property for two couples plus a guest, or a family of eight with three teenagers who do not need separate floors. The location holds at an Edgartown premium without the operational load of a larger estate.
What we would change: the master closet is small. For a peak-week stay with a formalwear element (Yacht Club gala season), borrow the guest closet.
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No. IX
The Oak Bluffs five-bedroom, East Chop bluff.
Bedrooms: 5. Sleeps: 10. Town: Oak Bluffs. Peak rate: $19,500 to $28,000 / week. Included: housekeeping twice a week, garden maintenance, East Chop Beach Club guest pass. Not included: pool, chef, daily housekeeping.
Why it ranks here: the East Chop bluff is the most overlooked editorial pocket on the island, with sound views, walking distance to the Inkwell Beach and the Oak Bluffs Carousel and Campground, and prices materially below Edgartown for comparable architecture. The 1898 Queen Anne refurbished in 2022 holds five bedrooms across two floors. No pool is the constraint and the Inkwell water gets crowded by noon on a July Saturday.
What we would change: the Oak Bluffs Steamship Authority Woods Hole ferry runs into the harbor 600 meters from the property; the morning car returns are audible from the porch.
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No. X
The Chappaquiddick five-bedroom, Wasque side.
Bedrooms: 5. Sleeps: 10. Town: Edgartown (Chappaquiddick). Peak rate: $22,000 to $32,000 / week. Included: over-sand-vehicle permit, four-wheel-drive station wagon on the rate, Wasque beach-stick. Not included: pool, chef, mainland-side daily access.
Why it ranks here: the only Chappaquiddick property on the editorial list. Wasque-side position, walking distance to Cape Poge Bay, and the over-sand-vehicle permit included on the rate (the structural draw of Chappy). Five bedrooms, no pool, the Chappy Ferry to the Edgartown side a constant operational item (the ferry runs every five to seven minutes in season but the queue on a July Sunday afternoon is real). Pick this only if the Chappy isolation is the point. The drive to a restaurant outside the Chappy Beach Club is a 25-minute round trip including the ferry.
What we would change: the upper-deck windbreak is the wrong height; the prevailing south-westerly catches the dining table.
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No. XI
The Aquinnah four-bedroom, Moshup Trail.
Bedrooms: 4. Sleeps: 8. Town: Aquinnah. Peak rate: $18,500 to $26,000 / week. Included: Moshup Beach pass, housekeeping twice a week. Not included: pool, chef, daily housekeeping, additional cars.
Why it ranks here: the value pick on the west end. Moshup Trail position, walking distance to the public Moshup Beach (the longest swimmable beach on the west end), an updated kitchen, and a four-bedroom layout that works for two families sharing. The drive to Chilmark Center is 12 minutes, the drive to the Vineyard Haven ferry is 38 minutes; this pocket is the trip, not the base for it. No pool. Beach is the swim.
What we would change: the second bathroom shower fixture is undersized. Pre-arrival, ask the manager to upgrade the shower head.
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No. XII
The West Tisbury four-bedroom, Tisbury Great Pond.
Bedrooms: 4. Sleeps: 8. Town: West Tisbury. Peak rate: $17,000 to $25,000 / week. Included: pond access for kayak and paddleboard, association beach pass to Long Point, gardener. Not included: pool, chef, additional cars.
Why it ranks here: the Tisbury Great Pond position holds the cut-to-the-sea every two years when the town opens the barrier beach to refresh the salinity. The property holds pond-front access, four bedrooms with an updated kitchen, and the Long Point association beach pass (a north-of-South-Beach answer that runs at a quarter the crowd density). The pond water is brackish and the swim is fine for adults; the family swim is at the Long Point beach.
What we would change: the kitchen sink runs slow on the drain.
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No. XIII
The Katama four-bedroom, second-row.
Bedrooms: 4. Sleeps: 8. Town: Edgartown (Katama). Peak rate: $16,500 to $24,000 / week. Included: heated pool, South Beach parking decal, two bikes. Not included: chef, daily housekeeping, beach-cabana service.
Why it ranks here: the smaller-group Katama answer. Second-row position (two streets back from the dunes) holds the price at materially below the front-row block while keeping the parking decal and the South Beach walking access. Four king bedrooms, 10-meter heated pool, a kitchen that fits a serving group of eight at the island. The bike-path access is 90 seconds. Right for a family of eight that wants the Katama-and-South-Beach trip without the front-row beach-house premium.
What we would change: the pool heater runs slow to bring the water above 78 degrees Fahrenheit; allow 36 hours on arrival before the swim.
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No. XIV
The Edgartown six-bedroom, Sengekontacket Pond.
Bedrooms: 6. Sleeps: 12. Town: Edgartown (Sengekontacket). Peak rate: $24,000 to $36,000 / week. Included: pond-front kayak inventory, Bend in the Road beach pass, daily housekeeping. Not included: pool, chef, second car.
Why it ranks here: the Sengekontacket Pond position is the under-the-radar editorial pick. Walking distance to the Bend in the Road beach (the calm-water alternative to South Beach for families with younger children), pond-front kayak access, six bedrooms across two floors, and a kitchen that holds 12. The State Beach causeway runs in front of the property; the road traffic in July is the constraint. The pool absence and the road noise pull the ranking; the architecture and the staff hold it on the list.
What we would change: the road-side bedrooms should be the kids’ rooms, not the masters. Manager has been told.
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