Holiday rentals in Tisbury

One Bedroom Cottage in Vineyard Haven

Small private cottage on a large quiet property nestled among trees with a wrap around deck. Perfect for a couple’s getaway weekend. Walk to Vineyard Haven shops, restaurants and Owen Park beach. It's one mile to town and the ferry (5 min drive/20 min walk with sidewalks). Cottage features vaulted ceilings, sitting room with kitchenette that includes coffee + tea station, mini fridge and microwave. Includes beach towels, toiletries, hairdryer & steam iron. Queen bed, AC, bath with tub & shower.

Walk to Main Street & Beach - No car needed!

New home, spacious 4 bedroom + 4 bath house at the end of a private road. NEWLY finished basement perfect for entertainment and additional guests. 3 to 4 minute walk to Owen Park beach (perfect for small children), the ferry, shops, a gym and pool (via Mansion House Inn), & restaurants. Chef’s kitchen fully stocked, features Viking appliances. Enjoy Wi-Fi, central A/C and heating units and TVs in every room with cable and streaming apps, Sonos speakers, a patio with grill and washer & dryer.

Vineyard Haven Guest House - A/C, Walk to Town

Queen bed up (large carpeted master suite/living room with vaulted ceiling, ceiling fans, and walk out to deck, This End Up Couch Set), bedroom with 2 twins down, full bathroom (renovated 2023) on first floor, AC throughout the house, washer dryer, 42" flat screen TV with Amazon Firestick and internet based Xfinity cable, grill, outdoor shower and hardwood floors downstairs. Short walk to downtown Vineyard Haven and short drive to many popular beaches! Quiet dead end street with own driveway.

Main Street steps from ferry

This freshly renovated 1 bedroom unit is a three minute walk from the Vineyard Haven ferry. Across the street begins Main Street Vineyard Haven with coffee, restaurants, shopping and local buses to everywhere. This one bedroom has a king bed in the bedroom and a comfortable brand new modern king pull out bed in the living room. There is also a twin rollaway bed. Full kitchen, sweet private small deck w seating for two overlooking Memorial Park. Perfect for visiting without a car. Free parking.

Vineyard Haven Walk to Ferry

I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

Family Friendly 5 BR, Walk to Town, Beach & Ferry!

Ideal rental for families and friends! Two fully equipped kitchens, two fully furnished outdoor spaces, oversized deck with grill, washer/dryer, sleeps 10 (2 King, 2 Queen, Full over Full bunk beds) 3 living spaces, 2 pack and plays, 2 full baths, outdoor shower, large yard, and central a/c in every room! No ferry ticket? No car? No problem! This home is located close enough to the Vineyard Haven ferry for a quick bike ride or comfortable walk. Walking distance to trails and beach!

Entire home newly renovated in August 2025

Step into your serene island getaway at 5 Pine Tree Lane, with 4 bedrooms (4 beds) and nestled in the heart of beautiful Martha’s Vineyard. This brand-new home blends modern comfort with Vineyard charm perfect for families, groups of friends, or couples looking for a relaxing escape. Walking distance to a neighborhood beach, year round ferry access (1mi) and shopping. This home was thoughtfully designed and offers everything you need for a peaceful and memorable experience.

Charming In-Town Retreat | Private Outdoor Spaces

This antique home originally built in 1801 is situated in the heart of Vineyard Haven. It was recently restored to include modern amenities while maintaining its historic charm. This quiet residence is just a quick walk from town, restaurants, shopping and the Steamship Authority. The large front lawn with majestic trees leads to a farmer's porch with rocking chairs. The private drive situated behind the house includes a Vermont slate walkway leading to a slate patio.

Carolyn's Vineyard Haven

LOCATION LOCATION LOCATION! Come enjoy this beautifully renovated 2000 + SF home, featuring 6 beds, 2 living rooms, 3 full marble baths, outdoor shower, and laundry. There are 2 decks with seating and grill area with plenty of trees for privacy. It is a 3 minute drive to VH ferry, 5 minute walk to Main Street shops/ restaurants and 5 minute walk to Tashmoo for a nice swim. Very close to Edgartown and Oak Bluffs making this a great location!

Immaculate Coastal Retreat!

Unwind in this stylish, sun-drenched second-floor apartment nestled in a quiet, tree-lined neighborhood. This apartment is just minutes from the heart of Vineyard Haven, numerous beaches and brackish Lake Tashmoo. Perfect for couples or a group of friends seeking a refined getaway, this beautifully designed 2-bedroom, 2-full+ bathroom retreat blends modern comforts with authentic island charm setting you up for an ideal get-away.

Martha's Vineyard Pied-á-terre #2 Vineyard Haven

Martha's Vineyard Pied-á-terre # 2 Vineyard Haven is but a short stroll from the ferry. Found in the heart of Vineyard Haven, this beautiful apartment is in the center of our village and it's mix of restaurants, shops, galleries and theaters. A seamless blend of comfort and convenience! If your dates are not available you can check our neighboring property Martha's Vineyard Pied-á-terre #1 Tisbury

The Pearl: Lovely cottage, close to VH town/ferry

THE PEARL is a lovely retreat for up to two couples. Come relax in this quaint cottage, close to town, beaches and ferry. Located in a quiet, residential neighborhood. Large yard and plenty of off-street parking. Walk to nearby beaches and restaurants. Significant DISCOUNTS for longer stays. Make an INQUIRY! Rent bikes or take island buses or taxis/Ubers. FRIDAY TO FRIDAY rentals in summer.