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.
alchemymv.com ↗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.
detentemv.com ↗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.
letoile.net ↗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.
19raw.com ↗Classic New England seafood and chops with waterfront seating overlooking Edgartown Harbor. Ideal for a long summer dinner watching the boats drift by. Great for families.
atlanticmv.com ↗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.
edgartownbooks.com ↗A Martha's Vineyard institution. Pick up fresh-baked pies, artisan breads, local produce, and farm-raised meats. Breakfast sandwiches in the morning are not to be missed. Open daily in season.
morninggloryfarm.com ↗Oak Bluffs' beloved craft brewery and pub — handcrafted ales, wood-fired pizza, and a classic island pub vibe. A short hop on the bus. Family-friendly and always lively.
offshoreale.com ↗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.
theporthunter.com ↗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. A quintessential Vineyard night out.
The Seafood Shanty · (508) 627-8622 ↗A legendary cash-only shack in Menemsha — some say the best fried clams on the island. Worth the short drive. Arrive early or expect a line. Eat on the dock as the sun sets. Perfect.
Google Maps: The Bite ↗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. The perfect bookend to any Vineyard trip.
lookoutmv.com ↗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. · Lifeguards in season.
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.
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.
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.
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.
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.
🚲 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.
Over 40 miles of dedicated paved bike paths connect the island's six towns and major beaches. Pick up bikes steps from the house.
Edgartown Bicycles ↗Sail out of Edgartown Harbor on a sunset cruise or full-day charter. Private and shared trips available — from classic schooners to luxury yachts.
Martha's Vineyard Times — Charter Listings ↗World-class striper, bluefish, and tuna fishing off Martha's Vineyard. Half-day and full-day charters depart from Edgartown Harbor throughout the season.
Visit Edgartown — Charter Guide ↗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.
Martha's Vineyard Museum ↗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.
Cape Pogue Wildlife Refuge ↗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.
Edgartown Shopping Guide ↗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.
MV Preservation Trust ↗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.
Sheriff's Meadow Foundation ↗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."
Martha's Vineyard Insider ↗A 20-minute bike ride or bus trip brings you to Oak Bluffs and the magical Victorian Campground — a National Historic Landmark of ornately painted gingerbread cottages. Worth an evening stroll.
Martha's Vineyard Campmeeting ↗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.
MV Online Activities Directory ↗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.
mvy.com — Aquinnah Guide ↗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.
Native Earth Teaching Farm ↗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.
Orange Peel Bakery ↗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.
The island has two standout courses. Farm Neck Golf Club in Oak Bluffs is a semi-private gem with sweeping views of Sengekontacket Pond — a Presidential favorite. Mink Meadows in Vineyard Haven offers a more relaxed round with lovely wooded fairways.
Farm Neck Golf Club ↗A beloved summer institution — the Vineyard Artisan Festivals bring together the island's finest makers every Thursday at the Grange Hall in West Tisbury. Browse handcrafted jewelry, ceramics, textiles, fine art, and local food products directly from the artisans who made them. It's a wonderful way to meet island creatives and bring something genuinely unique home.
Holiday editions in the fall are equally special — some guests plan their trip around them. Check the schedule online for dates and featured makers throughout the season.
Vineyard Artisan Festivals ↗The West Tisbury Farmers Market at the Grange Hall is the island's best — held Wednesday afternoons and Saturday mornings throughout the season. Expect extraordinary local produce, fresh flowers, artisan cheese, baked goods, and prepared foods from some of the island's finest growers.
Don't miss Morning Glory Farm in Edgartown — a true island institution with legendary corn, tomatoes, and baked goods just minutes from the house. Ghost Island Farm and Slip Away Farm also sell at market and direct from the farm. Stock the kitchen well — cooking here with local ingredients is half the joy.
West Tisbury Farmers Market ↗Martha's Vineyard's most celebrated ritual. The tiny fishing village of Menemsha faces due west — and every clear evening, locals and visitors gather on the beach with wine, lobster rolls, and lawn chairs to watch the sun sink into the Sound. Arrive an hour early to claim your spot.
While you're there: grab fresh-off-the-boat lobster and steamers from Larsen's Fish Market on the dock, or sit down at Home Port Restaurant for a classic island seafood dinner. Stroll Dutcher Dock to watch the draggers come in and pick up smoked bluefish to bring home. The Chilmark General Store nearby is worth a stop for a sandwich and local provisions on your way in.
Chilmark / Menemsha ↗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.
Island Alpaca Company ↗
🚌 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.