Vacation Rentals in Vineyard Haven, MA
Find stunning vacation rentals homes in Vineyard Haven on Martha’s Vineyard. Enjoy serene island living in an unforgettable home with Portfolio Properties.
Properties for rent in Vineyard Haven
Historic Victorian Gem in the Heart of Vineyard Haven
- 4 Bedrooms
- 3.0 Bathrooms
- Sleeps 8
- No pets
Charming Cottage in the Heart of Vineyard Haven - 1 Block from Harbor & Shops
- 1 Bedroom
- 1.0 Bathroom
- Sleeps 2
- No pets
Island Ease on Spring Hill - The Perfect Vineyard Haven Vacation Base
- 3 Bedrooms
- 2.5 Bathrooms
- Sleeps 8
- No pets
Midland Haven: Close-to-Town Vineyard Haven Retreat with Studio Suite/Media Loft
- 5 Bedrooms
- 4.5 Bathrooms
- Sleeps 10
- No pets
Private Lagoon-View Retreat with Hot Tub & Garden Patio, Dogs Welcome
- 3 Bedrooms
- 2.5 Bathrooms
- Sleeps 8
- No pets
Harbor-facing Elegance — 5-Bedroom Waterfront Retreat
- 5 Bedrooms
- 3.5 Bathrooms
- Sleeps 12
- No pets
Historic Vineyard Haven Village Retreat | 1 Block to Public Beach & Main Street
- 6 Bedrooms
- 2.5 Bathrooms
- Sleeps 11
- No pets
Private Lower Makonikey Retreat | 4BR Estate with Beach Access on 3 Acres
- 4 Bedrooms
- 4.0 Bathrooms
- Sleeps 8
- No pets
Charming 2 Bedroom Cottage in Vineyard Haven Close to Main Street
- 2 Bedrooms
- 2.0 Bathrooms
- Sleeps 6
- No pets
4 bedroom home with Pool in Vineyard Haven, Martha's Vineyard
- 4 Bedrooms
- 2.5 Bathrooms
- Sleeps 7
- No pets
Classic Island Cottage Near Town and Beaches
- 5 Bedrooms
- 3.0 Bathrooms
- Sleeps 10
- No pets
2 Bedroom Vineyard Haven House for rent on Martha's Vineyard
- 2 Bedrooms
- 1.0 Bathroom
- Sleeps 6
- Pets allowed
Vineyard Haven: The Year-Round Harbor Town
Vineyard Haven is often the first stop for many visitors to Martha’s Vineyard, as it serves as the island’s primary year-round ferry port. But it’s much more than just a gateway, it’s a lively harbor town with a mix of culture, dining, shopping, and history. With its working waterfront, thriving arts community, and convenient location, Vineyard Haven is a place where the island’s everyday life and vacation spirit intersect seamlessly.
What Makes Vineyard Haven Different?
Unlike other Vineyard towns that quiet down in the off-season, Vineyard Haven stays open year-round, making it a hub of island life. Here you’ll find a busy harbor filled with ferries, yachts, and fishing boats, along with shops and restaurants that welcome both summer visitors and local residents. Its combination of practicality and charm sets it apart; this is a town where you can stock up on essentials, enjoy fine dining, and take in a sunset on the harbor all in the same evening.
What Can You Do in Vineyard Haven?
The town is full of cultural and culinary highlights. For upscale dining right on the water, Garde East offers seasonal tasting menus and panoramic harbor views. For something more casual but equally satisfying, Waterside Market serves fresh sandwiches, salads, and baked goods. If you’re in the mood for Italian, Salvatore’s Ristorante has quickly become a favorite for authentic dishes with outdoor seating.
For shopping, Vineyard Haven is home to Bunch of Grapes Bookstore, a beloved independent shop, as well as galleries like Louisa Gould Gallery, which showcases maritime and island-inspired art. Clothing boutiques, jewelry shops, and home goods stores line Main Street, giving visitors plenty to browse.
If you’re looking for entertainment, catch a film or live performance at the historic Martha’s Vineyard Film Center, which regularly screens indie films, documentaries, and hosts festivals.
Where Can You Enjoy the Outdoors?
Vineyard Haven may feel like a bustling harbor town, but it also offers easy access to nature. Just outside the center, you’ll find Owen Park Beach, a small sandy stretch that’s perfect for a quick swim or picnic. For something more expansive, Lake Tashmoo offers opportunities for kayaking, paddleboarding, and scenic walks. Nearby, West Chop Lighthouse is a quiet spot to take in sweeping ocean views.
What Is Vineyard Haven Like at Night?
Evenings in Vineyard Haven are more relaxed than in Oak Bluffs, but the town still has plenty to offer. Dining along the harbor stretches well into the night, and you can often catch live music at local venues. Strolling down Main Street after dinner, ice cream in hand from Bernie’s Homemade Ice Cream, captures the simple pleasure of Vineyard Haven nights.
Why Stay in Vineyard Haven?
Vineyard Haven is the ideal choice if you want convenience paired with character. With its year-round ferries, wide variety of shops and restaurants, and balance between local life and vacation-friendly attractions, it makes a fantastic base for exploring the island. Vacation rentals here range from historic in-town homes to modern harbor front properties, many within walking distance of the ferry, shops, and beaches.
Ready to Experience Vineyard Haven?
Vineyard Haven offers the best of both worlds: an active harbor town full of dining, shopping, and culture, paired with easy access to quiet beaches and outdoor adventures. It’s a place where history and everyday island life blend seamlessly, making it both practical and picturesque.
Book your Vineyard Haven vacation rental today and enjoy a getaway that combines the convenience of a lively harbor with the charm and beauty of Martha’s Vineyard.
Four reasons buyers pick this side of the harbor.
A town that stays open year-round, a working harbor with shops and restaurants for locals and visitors alike, and easy access to nature five minutes from Main Street.
The town that does not close for the off-season.
Unlike other Vineyard towns that quiet down in the off-season, Vineyard Haven stays open year-round, making it a hub of island life. Because the Steamship Authority runs to this terminal every day of the year, the village stays active through the winter. The shops and restaurants here welcome both summer visitors and local residents, and there is a real year-round community to plug into.
- What’s nearby
- Tisbury School (K–8)
- Vineyard Haven Public Library
- MV Playhouse
- Cronig’s Market
A small in-town park, a bandstand, and a beach you can walk to.
Just outside the center, you will find Owen Park Beach, a small sandy stretch that is perfect for a quick swim or picnic. The park itself sits in the middle of the village, with a bandstand for summer concerts and a small green for picnics. The Black Dog schooners tie up next door. On a Tuesday night in July you can walk from a Main Street dinner to a free concert in the park and end up watching the sun fall behind the masts. None of it requires a car.
- What’s nearby
- Owen Park & Bandstand
- Owen Park Beach
- Black Dog Tavern & Wharf
- Steamship Authority Terminal
Bookstore, galleries, coffee, theater. All on one street.
Vineyard Haven is home to Bunch of Grapes Bookstore, a beloved independent shop, along with galleries like Louisa Gould Gallery, which showcases maritime and island-inspired art. Clothing boutiques, jewelry shops, and home goods stores line Main Street. For dining, Garde East offers seasonal tasting menus on the water, Waterside Market handles fresh sandwiches and baked goods, and Salvatore’s Ristorante has quickly become a favorite for authentic Italian. For entertainment, catch a film or live performance at the historic Martha’s Vineyard Film Center.
- What’s nearby
- Bunch of Grapes Bookstore
- Louisa Gould Gallery
- Garde East
- Waterside Market
- MV Film Center
A freshwater pond five minutes from town.
For something more expansive than an in-town swim, Lake Tashmoo offers opportunities for kayaking, paddleboarding, and scenic walks. The lake is a freshwater great pond opening to Vineyard Sound through a narrow inlet, popular with locals for shellfishing and calm swims away from the surf. Nearby, West Chop Lighthouse is a quiet spot to take in sweeping ocean views. The neighborhoods around the lake are residential, treed, and a long way from the summer crowd, while still being five minutes from a coffee on Main Street.
- What’s nearby
- Lake Tashmoo
- West Chop Lighthouse
- Tashmoo Overlook
- Wilfrid’s Pond Preserve
Vineyard Haven rentals at a glance.
Vineyard Haven is the only town with year-round Steamship service, so the rental market here is the most active in shoulder and off-season. Most rentals are walking distance to the ferry, Main Street, and Owen Park beach. Arrive without a car and the week is still walkable.
What you’ll be near
What you’ll be staying in
When to book
Questions renters ask about Vineyard Haven.
Answers our rental team gives most often when guests are planning a Vineyard Haven stay on Martha's Vineyard.
When should I book a Vineyard Haven rental for summer?
Most July and August Vineyard Haven rentals book between January and April. Walking-to-ferry homes and harbor-view properties go fastest. For peak summer, we recommend booking 3-5 months out.
What is the typical minimum stay for a Vineyard Haven rental?
In peak summer, most Vineyard Haven rentals are 7-night Saturday-to-Saturday bookings. In shoulder and off-season, 2-3 night minimums are common, which makes Vineyard Haven one of the most flexible rental towns for short stays.
Are pets allowed in Vineyard Haven vacation rentals?
About 25% of our Vineyard Haven rentals are pet-friendly. Pet policies are set by individual owners. Typical pet fees are $150-$300.
How much are cleaning fees for a Vineyard Haven rental?
Cleaning fees in Vineyard Haven typically range $250 to $475 depending on home size. The cleaning fee is shown on each listing before booking.
Can I walk to the ferry from a Vineyard Haven rental?
Many in-town Vineyard Haven rentals are within a 10-15 minute walk of the Steamship Authority terminal. Walking-to-ferry rentals are some of the most sought-after properties for short stays and ferry-only travelers.
Are Vineyard Haven rentals walkable to Main Street?
Many are. Vineyard Haven's downtown is compact, with rentals near Main Street, the harbor, and Owen Park within easy walking distance of restaurants, shops, the Bunch of Grapes Bookstore, and the Martha's Vineyard Film Center.
What is the off-season for Vineyard Haven rentals?
Off-season runs roughly October through May, but Vineyard Haven stays active year-round thanks to year-round ferry service, restaurants, and businesses. Many rentals are available year-round at 55-65% off peak rates.
Is Vineyard Haven a good rental spot for groups or couples?
Both work well. Vineyard Haven has small in-town cottages perfect for couples and short stays, plus larger harbor-view homes that fit groups. The walkability and ferry access make it especially good for car-free travelers.
What is the cancellation policy for a Vineyard Haven rental?
Cancellation policies vary by property. Most peak-season rentals require a non-refundable deposit and full payment 60-90 days before arrival. Travel insurance is available at booking.
Are Vineyard Haven rentals available year-round?
Many are. Vineyard Haven has the highest concentration of year-round rental availability on the Vineyard, thanks to year-round ferry service and active downtown businesses.
Reading for the Vineyard Haven curious.
Top Neighborhoods to Invest in Vineyard Haven, MA This Year
Where to look in the town of Tisbury right now, neighborhood by neighborhood, with a buyer’s lens on inventory, character, and long-term value.
Read articleThe Mansions of Vineyard Haven on Martha’s Vineyard
A look at the captain’s houses and grand summer estates that line William Street and the West Chop end of town, and the history behind them.
Read articleWaterfront Due Diligence on Martha’s Vineyard
If you are considering a harbor-facing home or a Lake Tashmoo property, read this first. A practical checklist covering FEMA, flood zones, septic, and coastal access rights.
Read articlePlanning a stay in Vineyard Haven?
Portfolio Properties manages one of the most curated selections of Vineyard Haven vacation rentals on Martha's Vineyard. From in-town walkable homes near Main Street to quieter properties along Lake Tashmoo, Vineyard Haven rentals give you ferry-walking convenience and year-round island energy. 25 years working the Vineyard Haven market means we know which homes deliver what they promise.