Charming 2 Bedroom Cottage in Vineyard Haven Close to Main Street

2 Bedrooms2.0 Baths6 GuestsNo PetsHOUSE in Vineyard Haven
Living area with natural light, a beige sofa accented by patterned pillows, and woven rattan chairs around a matching coffee table. - property
Living area with natural light, a beige sofa accented by patterned pillows, and woven rattan chairs around a matching coffee table.
Exterior view of the cottage with weathered wood shingles, a dormer window, and a tall green hedge lining the front path.
Two windows flank a queen bed dressed in white linens and a textured blue throw in the bright bedroom.
Two twin beds with blue throws flank a checkered rug beneath sloped white ceilings and soft wall sconces.
Front porch entrance with weathered cedar shingles, white trim, and surrounding green shrubs under a clear blue sky.Sunlit exterior view of weathered shingle siding, white-trimmed windows, and a grassy yard bordered by tall trees.Two wooden armchairs with white cushions sit on a shaded porch with cedar shingle siding and a gray-trimmed window.Living room featuring a navy sofa with gray and striped pillows, a wooden coffee table, and a patterned armchair.A wooden coffee table holds a black tray with books and a remote in front of the navy sofa.Natural light fills the seating area with two rope-accented armchairs, a woven coffee table, and a glowing table lamp.Light-filled sitting room with beige sofa, woven armchairs, rattan coffee table, and hardwood floors.Kitchen with white cabinetry, stainless steel appliances, dark countertops, and a window over the sink.Dining area with wood table, cross-back chairs, a cushioned bench, white wainscoting, and sliding glass doors to the deck.Dining area with dark wood table, blue upholstered bench and chairs, black metal coat rack, and hardwood floors.Wood deck patio with black woven seating, white cushions, a stainless steel grill, and wooded backyard views.Bedroom with a gray upholstered headboard, white linens, blue textured throw, and matching bedside lamps by a window.Laundry area with stacked washer and dryer, open shelving with towels, and hardwood floors leading to a bathroom.Bathroom with white paneled walls, a window with a roller shade, and a shower curtain beside a toilet and vanity.Narrow hallway with white beadboard walls, a paneled door with glass panes, and built-in storage on one side.Stairwell with white walls, wooden handrails, and a single hanging glass pendant light above.Hallway with hardwood floors, white walls, a glass pendant light, and a curtained doorway next to a stairwell.Compact kitchen with light wood cabinetry, black countertops, stainless steel fridge, and adjacent round dining table.Seating area with navy sofa, patterned pillows, tan leather armchair, wall-mounted flat-screen TV, and natural wood floors.Family room with navy sectional, round wood coffee table, leather armchair, and floor lamp by windows.Hallway with white walls, recessed ceiling light, hardwood floors, and a patterned runner rug leading to a bathroom.Attic bedroom with two twin beds, white linens, blue throws, hardwood floors, and a multi-color checkered rug.Compact bathroom with built-in shelving above the toilet holding folded towels and storage baskets.Outdoor shower with weathered wooden enclosure, gray shingle siding, and a white paneled door nearby.Spacious backyard with green lawn, surrounded by trees, and a gray shingle-sided house with a dark wood deck.Black and white floor plan showing two levels with labeled rooms, dimensions, and outdoor decks.Floor plan showing layout with two bedrooms, kitchen, dining area, sitting room, porch, decks, and bathroom with walk-in closet.Black-and-white floor plan showing layout of first floor with living room, eat-in kitchen, bedroom, bath, and two halls.

Property Details

Freshly Renovated Vineyard Haven Cottage | NEW Vacation Rental Be among the first guests to enjoy this charming Vineyard Haven retreat, offered as a vacation rental for the very first time. Thoughtfully updated while maintaining its classic Martha’s Vineyard character, this inviting two-bedroom, two-bath home offers the perfect setting for families, couples, or friends seeking a relaxing Island getaway. Bright interiors, comfortable furnishings, and peaceful outdoor spaces create an easygoing atmosphere where mornings begin with coffee on the deck and evenings end beneath the Vineyard stars. The main living area is warm and welcoming, with abundant natural light and comfortable seating, including a queen sleeper sofa to accommodate additional guests. Adjacent to the living room, the dining area offers ample space for gathering over meals prepared in the fully equipped kitchen. The home comfortably sleeps up to six guests. Outside, a spacious backyard offers room for lawn games, family fun, or simply enjoying the quiet surroundings. A sunny elevated deck is ideal for outdoor dining, relaxing with a book, or unwinding after a day exploring the Island. Located in a quiet residential neighborhood, the home offers convenient access to everything Vineyard Haven has to offer. Spend your days exploring boutique shops, waterfront restaurants, local galleries, ferry arrivals, Owen Park Beach, Tisbury Town Beach, and nearby Island bike paths. From here, every corner of Martha’s Vineyard is within easy reach. Whether you’re planning beach days, cycling adventures, or simply looking for a peaceful place to reconnect with family and friends, this welcoming Vineyard Haven cottage makes an ideal home base for your Island vacation. ⸻ Highlights * NEW to the vacation rental market * Sleeps up to 6 guests * 2 Bedrooms * 2 Full Bathrooms * Queen sleeper sofa in living room * Bright, newly refreshed interiors * Spacious backyard * Outdoor deck with seating * Quiet residential neighborhood * Minutes from downtown Vineyard Haven * Convenient access to ferry, beaches, restaurants, and shopping * Ideal for families, couples, or small groups ⸻ Sleeping Arrangements Bedroom 1 * Queen Bed Bedroom 2 * 2 Twin Beds Living Room * Queen Sleeper Sofa Maximum Occupancy: 6 Guests ⸻ Why Guests Love This Home Unlike many vacation rentals that have been heavily used over the years, this home is making its debut as a seasonal rental. Guests will enjoy fresh furnishings, comfortable coastal décor, inviting outdoor living spaces, and the opportunity to experience one of Vineyard Haven’s most convenient neighborhoods from a home that feels thoughtfully prepared for visitors.

Sleeping Arrangements

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

Living Room 1

1 Sofa Bed

Amenities

Attractions

  • Museums

Entertainment

  • Television

Features

  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Internet - Wifi
  • Iron and Board
  • Linens Provided
  • Living Room
  • Towels Provided
  • Washing Machine

Kitchen

  • Coffee Maker
  • Cookware
  • Dining Area
  • Dining Table
  • Dishes & Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster

Leisure

  • Antiquing
  • Bird Watching
  • Boating
  • Horseback Riding
  • Shopping
  • Wildlife Viewing

Local

  • Fitness Center
  • Hospital

Location

  • Near Ocean
  • Town

Outdoor

  • Deck/Patio
  • Gas Grill

Safety

  • Carbon Monoxide Detector
  • Emergency Exit Route
  • Fire Emergency Contact
  • Fire Extinguisher
  • First Aid Kit
  • Medical Emergency Contact
  • Smoke Detector

Sports

  • Biking
  • Fishing
  • Fishing Bay
  • Fishing Surf
  • Golf Optional
  • Hiking
  • Mountain Biking
  • Pier Fishing
  • Sailing
  • Swimming
  • Tennis

Themes

  • Family

Availability

2026
October 2026
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Location

101 Midland Avenue
Vineyard Haven, MassachusettsOpen in Maps

Policies

Cancellation Policy

CANCELLATION POLICY: In the event of a cancellation Tenant must notify Portfolio Properties in writing. Portfolio Properties will then make every effort to re-rent this property for the lease rental period. If the property is re-rented for the full rental period at the amount specified in this lease document, a refund will be issued less 15% of the total amount of the lease to be retained by Portfolio Properties. In the event Portfolio Properties is unable to re-rent the property, the tenant agrees to be responsible for the full amount of the rental as outlined in the payment schedule. If Portfolio Properties is able to re-rent the property for less than the full rental amount, the tenant will be responsible for 15% of the original rental amount and any difference between the original rate and the new rental rate.

Deposit Policy

Initial payment (50% of the rental rate as well as associated fees) is due at booking and the remaining amount is due 60 day prior to arrival. This initial payment MUST be received no later than 48 hours from confirming your reservation, otherwise the dates will be released.

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