Vacation Rentals
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Lovely Modern Farmhouse in Lambert's Cove with a Stunning Pool!
House in West Tisbury, MA
- 3 Bedrooms
- 4.5 Bathrooms
- Sleeps 8
- No pets
From $11,000 / week
Historic Victorian Gem in the Heart of Vineyard Haven
House in Vineyard Haven, MA
- 4 Bedrooms
- 3.0 Bathrooms
- Sleeps 8
- No pets
From $4,000 / week
A Light-filled Katama Escape Near Edgartown & the Ocean
House in Edgartown, MA
- 3 Bedrooms
- 4.5 Bathrooms
- Sleeps 10
- No pets
From $5,500 / week
Modern Makonikey Guesthouse – Beach Access, Sunset Roof Deck & Ocean Views
Guesthouse in West Tisbury, MA
- 2 Bedrooms
- 1.0 Bathroom
- Sleeps 4
- No pets
From $4,000 / week
West Tisbury Haven: Central Island Comfort with Vineyard Charm
Cottage in West Tisbury, MA
- 4 Bedrooms
- 2.5 Bathrooms
- Sleeps 8
- No pets
From $7,000 / week
Waterfront Post & Beam Masterpiece on Sengekontacket Pond
House in Oak Bluffs, MA
- 4 Bedrooms
- 4.0 Bathrooms
- Sleeps 10
- No pets
From $10,000 / week
Historic Edgartown Estate with Heated Pool & Spa
House in Edgartown, MA
- 5 Bedrooms
- 7.0 Bathrooms
- Sleeps 10
- No pets
From $14,000 / week
Charming Cottage in the Heart of Vineyard Haven - 1 Block from Harbor & Shops
Guesthouse in Vineyard Haven, MA
- 1 Bedroom
- 1.0 Bathroom
- Sleeps 2
- No pets
From $4,500 / week
Private Vineyard Retreat with Guest Cottage | 4.5 Acres of Island Serenity
House in West Tisbury, MA
- 4 Bedrooms
- 3.5 Bathrooms
- Sleeps 8
- No pets
From $7,500 / week
Private West Tisbury Guest House Retreat | Peaceful Vineyard Getaway
Guesthouse in West Tisbury, MA
- 2 Bedrooms
- 1.0 Bathroom
- Sleeps 4
- No pets
From $4,000 / week
Island Ease on Spring Hill - The Perfect Vineyard Haven Vacation Base
House in Vineyard Haven, MA
- 3 Bedrooms
- 2.5 Bathrooms
- Sleeps 8
- No pets
From $3,700 / week
Midland Haven: Close-to-Town Vineyard Haven Retreat with Studio Suite/Media Loft
House in Vineyard Haven, MA
- 5 Bedrooms
- 4.5 Bathrooms
- Sleeps 10
- No pets
From $5,500 / week
Charming Edgartown Village Cottage Close to Town & Fuller Street Beach
Cottage in Edgartown, MA
- 2 Bedrooms
- 1.0 Bathroom
- Sleeps 4
- No pets
From $4,000 / week
"The Westlake House": Waterfront Bluff-Top Cottage w/ Pvt Beach & Lagoon Views
House in Oak Bluffs, MA
- 3 Bedrooms
- 2.0 Bathrooms
- Sleeps 6
- Pets allowed
From $3,500 / week
Private Lagoon-View Retreat with Hot Tub & Garden Patio, Dogs Welcome
House in Vineyard Haven, MA
- 3 Bedrooms
- 2.5 Bathrooms
- Sleeps 8
- No pets
From $3,500 / week
Modern Katama Bay Retreat with Stunning Water Views & Ultimate Beach Proximity
House in Edgartown, MA
- 3 Bedrooms
- 3.0 Bathrooms
- Sleeps 6
- No pets
From $6,000 / week
A Chappaquiddick Escape: A Modern Coastal Cottage at Katama Bay
House in Edgartown, MA
- 3 Bedrooms
- 1.5 Bathrooms
- Sleeps 8
- No pets
From $3,000 / week
Bright & Breezy Edgartown Cape Near Beaches and Bike Paths. Dogs welcome!
House in Edgartown, MA
- 3 Bedrooms
- 2.0 Bathrooms
- Sleeps 6
- Pets allowed
From $3,500 / week
Private Edgartown Escape with Hot Tub & Screened-In Porch
House in Edgartown, MA
- 3 Bedrooms
- 2.5 Bathrooms
- Sleeps 6
- No pets
From $3,000 / week
Harbor-facing Elegance — 5-Bedroom Waterfront Retreat
House in Vineyard Haven, MA
- 5 Bedrooms
- 3.5 Bathrooms
- Sleeps 12
- No pets
From $4,200 / week
Historic Vineyard Haven Village Retreat | 1 Block to Public Beach & Main Street
House in Vineyard Haven, MA
- 6 Bedrooms
- 2.5 Bathrooms
- Sleeps 11
- No pets
From $4,200 / week
Private Lower Makonikey Retreat | 4BR Estate with Beach Access on 3 Acres
House in Vineyard Haven, MA
- 4 Bedrooms
- 4.0 Bathrooms
- Sleeps 8
- No pets
From $4,000 / week
Edgartown Retreat Nestled Between Felix Neck & Manuel Correllus State Forest
House in Edgartown, MA
- 3 Bedrooms
- 2.0 Bathrooms
- Sleeps 6
- No pets
From $4,000 / week
Contemporary Edgartown Retreat with Vaulted Ceilings & Expansive Deck
House in Edgartown, MA
- 4 Bedrooms
- 3.0 Bathrooms
- Sleeps 8
- No pets
From $4,000 / week
Spacious Katama Farmhouse with Conservation Views & Expansive Grounds
House in Edgartown, MA
- 5 Bedrooms
- 3.0 Bathrooms
- Sleeps 8
- No pets
From $6,000 / week
Charming Katama Guest House with Conservation Views & Western Style
Guesthouse in Edgartown, MA
- 2 Bedrooms
- 1.5 Bathrooms
- Sleeps 5
- No pets
From $2,500 / week
Classic Edgartown Colonial with Screened Porch & Outdoor Shower
House in Edgartown, MA
- 4 Bedrooms
- 2.0 Bathrooms
- Sleeps 8
- No pets
From $5,000 / week
Chilmark Contemporary with Ocean Views, Private Beach Access & Privacy
House in Chilmark, MA
- 5 Bedrooms
- 3.5 Bathrooms
- Sleeps 9
- No pets
From $12,500 / week
Elegant Chilmark Retreat with Expansive Decks, Jacuzzi & Coastal Setting
House in Chilmark, MA
- 5 Bedrooms
- 5.5 Bathrooms
- Sleeps 12
- No pets
From $10,000 / week
Top-Floor Seaview Condo with Sweeping Ocean Views & Private Balcony
Condo in Oak Bluffs, MA
- 2 Bedrooms
- 2.0 Bathrooms
- Sleeps 4
- No pets
From $4,200 / week
Seaview Condo #203 with Ocean Views & Private Balcony in Oak Bluffs
Condo in Oak Bluffs, MA
- 2 Bedrooms
- 2.0 Bathrooms
- Sleeps 4
- No pets
From $4,100 / week
Spacious Edgartown Retreat with Studio & Dual Outdoor Showers
House in Edgartown, MA
- 4 Bedrooms
- 4.0 Bathrooms
- Sleeps 10
- Pets allowed
From $6,500 / week
Luxury Katama Estate with Pool, Swim-Up Bar & Screened Porch Retreat
House in Edgartown, MA
- 5 Bedrooms
- 5.5 Bathrooms
- Sleeps 12
- No pets
From $22,000 / week
Mill Pond–Front West Tisbury Farmhouse with Scenic Water Views
House in West Tisbury, MA
- 4 Bedrooms
- 3.5 Bathrooms
- Sleeps 7
- No pets
From $7,000 / week
Spacious Meadow View Farms Retreat with Tennis, Pickleball & Multiple Decks
House in Oak Bluffs, MA
- 4 Bedrooms
- 3.0 Bathrooms
- Sleeps 10
- No pets
From $9,000 / week
Charming 6 Bdrm 4 Ba East Chop Vacation rental!
House in Oak Bluffs, MA
- 6 Bedrooms
- 4.0 Bathrooms
- Sleeps 12
- No pets
From $7,500 / week
Charming 2 Bedroom Cottage in Vineyard Haven Close to Main Street
House in Vineyard Haven, MA
- 2 Bedrooms
- 2.0 Bathrooms
- Sleeps 6
- No pets
From $3,500 / week
Field House in Katama with Heated Pool
House in Edgartown, MA
- 4 Bedrooms
- 2.5 Bathrooms
- Sleeps 8
- No pets
From $7,400 / week
4 bedroom Ocean Front for rent in Oak Bluffs, Martha's Vineyard
House in Oak Bluffs, MA
- 4 Bedrooms
- 3.0 Bathrooms
- Sleeps 12
- No pets
From $10,000 / week
Edgartown Home for Rent With Indoor Heated Pool | Private Chappaquiddick Retreat
House in Edgartown, MA
- 4 Bedrooms
- 4.0 Bathrooms
- Sleeps 8
- No pets
From $5,000 / week
4 bedroom home with Pool in Vineyard Haven, Martha's Vineyard
House in Vineyard Haven, MA
- 4 Bedrooms
- 2.5 Bathrooms
- Sleeps 7
- No pets
From $16,000 / week
New Oak Bluffs Vacation Home hosts Pool & Grill
House in Oak Bluffs, MA
- 4 Bedrooms
- 2.5 Bathrooms
- Sleeps 8
- No pets
From $31,050 / week
Edgartown Four-Bedroom for rent Close to Town & Beaches
House in Edgartown, MA
- 4 Bedrooms
- 2.0 Bathrooms
- Sleeps 9
- No pets
From $3,339 / week
Family-Friendly Fun & Convenient Location | Oak Bluffs
House in Oak Bluffs, MA
- 3 Bedrooms
- 2.5 Bathrooms
- Sleeps 7
- No pets
From $3,500 / week
Ride the Island with Ease | Newly Built 6BR Compound on Bus Route
House in Oak Bluffs, MA
- 6 Bedrooms
- 3.5 Bathrooms
- Sleeps 13
- No pets
From $38,000 / week
Classic Island Cottage Near Town and Beaches
House in Vineyard Haven, MA
- 5 Bedrooms
- 3.0 Bathrooms
- Sleeps 10
- No pets
From $5,000 / week
Quiet Oak Bluffs apartment w/ grill
Apartment in Oak Bluffs, MA
- 2 Bedrooms
- 1.0 Bathroom
- Sleeps 5
- No pets
From $8,100 / week
2 Bedroom Private Guest Suite in Oak Bluffs
Guesthouse in Oak Bluffs, MA
- 2 Bedrooms
- 1.0 Bathroom
- Sleeps 5
- No pets
From $8,190 / week
2 Bedroom Vineyard Haven House for rent on Martha's Vineyard
House in Vineyard Haven, MA
- 2 Bedrooms
- 1.0 Bathroom
- Sleeps 6
- Pets allowed
From $3,700 / week
Chappy Water Views with Stretching Yard for Your Family of 6
House in Edgartown, MA
- 3 Bedrooms
- 1.5 Bathrooms
- Sleeps 6
- No pets