99 Cooke Street · Downtown Edgartown, MA 02539
Your Guest Guide




Set just one block from Main Street in the heart of Edgartown Village, this beautifully updated four-bedroom cottage is your home base for the perfect Martha's Vineyard escape.
The open-concept first floor flows through French doors onto a private brick terrace and into the backyard — centered on a heated 9' × 21' gunite pool with integrated spa. Upstairs, two generous en suite bedrooms. Below, a finished lower level with a fourth bedroom retreat.
Everything is stocked and ready. All that's left is to arrive.
Take an immersive 360° tour of 99 Cooke Street before you arrive.
A few simple guidelines to keep the house in wonderful shape for everyone. Thank you for helping us maintain this special place.
Edgartown has one of New England's best dining scenes. Reservations are strongly recommended in summer — book ahead, especially for weekends.
Sophisticated contemporary American in the heart of Edgartown. Seasonal menu with locally sourced ingredients — try the lobster mac and grilled octopus. One of the island's most celebrated tables.
Tap for contact ↓A beloved local institution tucked in a twinkle-lit courtyard. Inventive American dishes, outstanding wine program, and one of the most romantic atmospheres on the island. Booking essential.
Tap for contact ↓French-inspired elegance with over 30 years of island history. Classic dishes like escargot and bouillabaisse alongside modern interpretations. Wine list of 800+ bottles. A special-occasion staple.
Tap for contact ↓Arguably the best raw bar on Martha's Vineyard. Just off Main Street — fresh island oysters, lobster roll sliders with caviar, and dry-aged steaks. Casual but exceptional. Arrive early.
Tap for contact ↓Right on Main Street at number 55 — locally owned since 2012 and named after an actual 1918 shipwreck in Vineyard Sound. Fresh local seafood, oysters, fish tacos, and steak, with a lively late-night bar scene. Open May through October.
Tap for contact ↓A beloved Edgartown institution for over 50 years at 31 Dock Street, right on the harbor. Sushi, raw bar, lobster quesadilla, and sustainably caught local seafood — with wraparound deck views and live music.
Tap for contact ↓Hidden behind Edgartown Books — morning buns, cruffins and coffee by day; oysters, lobster linguine and cocktails by night. A local gem worth seeking out. Relaxed and creative.
Tap for contact ↓A charming Edgartown breakfast and lunch spot at 17 Mayhew Lane. Open daily 8AM–2PM with a lovely outdoor patio — ideal for a leisurely morning before the beach. Takeout available.
Tap for contact ↓A chef-owned Edgartown gem at 218 Upper Main Street. Everything homemade — farm-fresh breakfast and lunch Tue–Sun 8AM–2:30PM, dinner Fri–Sat. Local seafood, free-range meats, and great vegetarian options.
Tap for contact ↓Seasonally driven cuisine in the heart of downtown Edgartown. Creative, locally sourced dishes in a warm, welcoming space. Open Wed–Mon, Memorial Day through Columbus Day. Reservations recommended.
Tap for contact ↓An Oak Bluffs favorite for fresh, creative comfort food. Relaxed atmosphere with a seasonal menu focused on locally sourced ingredients. A short drive or bus ride from the house.
Tap for contact ↓One of our personal favorites — a great casual stop whether you're arriving or heading off island. Cold drinks, good food, and a laid-back vibe that immediately puts you in the island mindset.
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Martha's Vineyard is blessed with extraordinary coastline. Here are the best beaches within reach of the house — each with its own character.
Three miles of rolling Atlantic surf and golden dunes — named one of Travel & Leisure's world's best beaches. Perfect for bodysurfing and long walks. A 10-minute bike or drive south. Adjacent Norton Point allows over-sand driving with a permit. · Lifeguards in season.
Tap for directions ↓A calm, gentle stretch between Edgartown and Oak Bluffs — ideal for families with young children. Home to the famous "Jaws Bridge," where locals leap into the water below. Easy 10-minute bike ride from the house.
Tap for directions ↓The most convenient beach to downtown Edgartown — warm, calm harbor water, sandy shores, and a 10-minute walk from the house. A favorite for families with young children. Faces the outer harbor toward Chappaquiddick.
Tap for directions ↓Postcard-perfect. The classic white lighthouse watches over this town beach at the tip of North Water Street — stunning harbor views, easy access, and a beautiful spot for sunrise. A stroll straight from the house.
Tap for directions ↓A quieter, locals-favored stretch on the way to Oak Bluffs. Excellent for kiteboarding, windsurfing, and swimming. Calm enough for paddleboarding on most days. Parking available nearby.
Tap for directions ↓Take the legendary 2-minute Chappy Ferry from Edgartown dock to access wild, uncrowded beaches on "Chappy." East Beach and Cape Pogue are particularly spectacular — bring a picnic and make a day of it. Both are Trustees of Reservations properties; check their site for any closures before you go.
Tap for directions ↓🚲 Bikes from the house reach most Edgartown beaches in under 15 minutes via dedicated island bike paths.
Martha's Vineyard rewards every pace — from leisurely gallery walks to open-water sailing. Here are our favorite ways to spend the days.
Sail out of Edgartown or Vineyard Haven on a sunset cruise, day sail, or private charter. Options range from classic catboats to tall ship schooners and catamarans.
Tap for links ↓World-class striper, bluefish, and tuna fishing off Martha's Vineyard. Half-day and full-day charters depart from Edgartown and Oak Bluffs throughout the season.
Tap for links ↓Kayaking, paddleboarding, surfing lessons at South Beach, and windsurfing at Bend-in-the-Road. Multiple outfitters on the island offer rentals and guided experiences for all levels.
Tap for links ↓Two standout courses — Farm Neck Golf Club in Oak Bluffs with sweeping pond views, and Mink Meadows in Vineyard Haven for a relaxed round through wooded fairways.
Tap for links ↓Over 40 miles of dedicated paved bike paths connect the island's six towns and major beaches. Pick up bikes steps from the house.
Tap for links ↓Cedar Tree Neck Sanctuary in West Tisbury offers serene woodland trails down to a secluded beach. Free year-round. Sheriff's Meadow and Felix Neck Wildlife Sanctuary are also nearby highlights.
Tap for links ↓Hop the 2-minute Chappy Ferry from Edgartown dock to this peaceful island sanctuary. Explore the stunning Mytoi Japanese Gardens, secluded beaches, and nature trails at Trustees of Reservations.
Tap for links ↓A 30-minute drive takes you to the dramatic multicolored clay cliffs at the island's western tip — a National Historic Landmark. Arrive for sunset and explore the beautiful beach below the cliffs.
Tap for links ↓The island's most celebrated ritual. The tiny fishing village faces due west — locals and visitors gather with wine, lobster rolls, and lawn chairs to watch the sun sink into the Sound. Arrive an hour early.
Tap for directions ↓The iconic white lighthouse at the harbor's edge is a 10-minute walk from the house. Visit at sunrise for the best light and fewest crowds. The surrounding beach is lovely for a morning stroll.
Tap for links ↓One of New England's finest examples of Greek Revival architecture, dating to 1843. Now a performing arts center — check the summer schedule for concerts, films, and lectures.
Tap for links ↓A 20-minute bike ride brings you to the magical Victorian Campground — a National Historic Landmark of ornately painted gingerbread cottages. Worth an evening stroll.
Tap for links ↓West Tisbury Farmers Market — Wednesday afternoons and Saturday mornings. Don't miss Morning Glory Farm in Edgartown. Stock the kitchen well — cooking here with local ingredients is half the joy.
Tap for links ↓Every Thursday at the Grange Hall in West Tisbury — handcrafted jewelry, ceramics, textiles, and fine art directly from island makers. Holiday editions in the fall are equally special.
Tap for links ↓Main Street Edgartown is lined with art galleries, boutique shops, and independent booksellers. Don't miss Edgartown Books, Carly Simon's Midnight Farm in Vineyard Haven, and the weekly farmers market.
Tap for links ↓One of the island's most beloved quirky traditions — morning yoga in an open field while friendly goats wander around (and occasionally climb on) you. Book ahead, spots fill fast in season.
Tap for links ↓A delightful stop for all ages in Oak Bluffs — meet and feed a herd of friendly alpacas roaming open pastures. The farm shop sells gorgeous hand-spun alpaca wool goods, a perfect island keepsake.
Tap for links ↓The 1975 Spielberg classic was filmed almost entirely on Martha's Vineyard. The Amity Tour visits iconic locations including the harbor, South Beach dunes, and the legendary "Jaws Bridge."
Tap for links ↓A West Tisbury institution. On select evenings the wood-fired oven turns out incredible pizza — grab a pie, find a spot on the lawn, and settle in. Bring a bottle and enjoy the island pace.
Tap for links ↓The island's most devoted morning queue — and worth every minute. Pro tip: send the kids next door to the arcade while the grown-ups hold the spot in line. Fresh, hot, and gone by midday.
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🚌 VTA bus stops on Main Street — free island-wide service.
🚲 Bike paths connect Edgartown to all major beaches.
Practical info for getting here, getting around, and stocking up.
Everything you need while you're here.
Control spa temperature, pool lights, and heating from your phone.
Requires 99Cooke WiFi · iPad also poolside
Tap to flip backSmart lighting controls coming soon.