Dukes Area Rentals
From $720 per night (USD)VRBO
3-bedroom house in charming Oak Bluffs with WiFi, AC. Start your vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Make yourself at home in this 3-bedroom Oak Bluffs retreat. This beautiful house features 2 king beds, 1 queen bed, a fu ...
From $720 per night (USD)VRBO
From $580 per night (USD)Expedia
Downtown brand new construction 3 bed & 3 bath
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Brand-new, high-end 3BR/3BA home in the heart of Vineyard Haven—just one block from the ferry terminal. Walk to restaura ...
From $580 per night (USD)Expedia
From $1461 per night (USD)VRBO
Walk to Edgartown! Sun at South Beach! Privacy & relaxation at special home.
- Bedrooms:
- 4
- Bathrooms:
- 1
- Sleeps:
- 10
IMMACULATE, CONVENIENT, CHARMING! Big Families & Groups of Friends LOVE this house! First floor has comfortable open f ...
From $1461 per night (USD)VRBO
From $452 per night (USD)VRBO
Short Walk to Town - Nice Comfortable -Reasonable
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This property is new to VRBO, however it has been hosting guests for several years on another site with 5 star reviews. ...
From $452 per night (USD)VRBO
From $1223 per night (USD)VRBO
Charming 3-bedroom family home with WiFi and AC in Vineyard Haven.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy this family home with 3 bedrooms, a spacious loft with half bath, and comfortable amenities. This property has a l ...
From $1223 per night (USD)VRBO
From $776 per night (USD)VRBO
Completely Renovated Oak Bluffs Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Fully renovated for 2025, this stylish 3-bed, 2.5-bath townhome invites you to unwind with a community pool, tennis cour ...
From $776 per night (USD)VRBO
From $1691 per night (USD)VRBO
6bedroom, 4bath, chefs kitchen, central air, ping pong, walking distance to town
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 13
This NEWLY RENOVATED 6-bedroom house in Vineyard Haven is just a 10 minute walk to public beach, downtown restaurants, b ...
From $1691 per night (USD)VRBO
From $1224 per night (USD)Expedia
Modern 4BR Escape w Jeep Wrangler. Near Town. Patio, Fire Pit & Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your vacation retreat! This recently renovated single-family near downtown Vineyard Haven blends high-end fin ...
From $1224 per night (USD)Expedia
From $906 per night (USD)VRBO
Walk to town & beach A/C, Strong WiFi, family & pet friendly. Outdoor shower
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summertime! And the living is easy in this comfortable, casual home on Martha's Vineyard. The large front deck is great ...
From $906 per night (USD)VRBO
From $591 per night (USD)Expedia
Spacious colonial home close to town with AC, porches, & W/D
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Seabreeze Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $591 per night (USD)Expedia
From $614 per night (USD)VRBO
Spacious 4-bedroom house in charming West Tisbury
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Escape to a wonderful 4-bedroom house in West Tisbury. This serene retreat features a king bed, full bed, queen bed, and ...
From $614 per night (USD)VRBO
From $1452 per night (USD)Expedia
Stunning Tisbury Retreat with Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Escape to this brand-new luxury home in Vineyard Haven, minutes from downtown and the ferry. Designed for comfort and st ...
From $1452 per night (USD)Expedia
From $804 per night (USD)VRBO
Downtown Edgartown, Prime Location, Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to your Martha's Vineyard escape in the heart of downtown. This charming home is just two blocks from the histor ...
From $804 per night (USD)VRBO
From $311 per night (USD)Expedia
Quaint, ranch style home in Oak Bluffs with central air
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
The Rootskeller Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $311 per night (USD)Expedia
From $838 per night (USD)VRBO
Charming 3BR Vineyard Retreat, Lg Deck w/ Kitchen, Near Beach, Town Ctr & Ferry
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to RoBree Farm – Your Martha’s Vineyard Retreat in the Heart of Oak Bluffs Escape to the serenity and magic of ...
From $838 per night (USD)VRBO
From $677 per night (USD)Expedia
Charming home with walkable beach, large yard, deck, fire pit, and A/C
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Beach House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $677 per night (USD)Expedia
From $420 per night (USD)VRBO
Charming 2-bedroom townhouse in Oak Bluffs with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Sengekontacket pond in Oak Bluffs is waiting for you at this quiet 2-bedroom townhouse with a private deck overlooking a ...
From $420 per night (USD)VRBO
From $561 per night (USD)VRBO
Orginal 1710 Farmhouse Seeks Artist, Writer, Composer or Musician
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
1710 Farmhouse In Chilmark Convenient North Road location - close to Menemsha Beach, Chilmark Store and picturesque hiki ...
From $561 per night (USD)VRBO
From $512 per night (USD)VRBO
Aquinnah cottage private,serene, easy beach access ,sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Aquinnah cottage on a private road with a short drive to the amazing beaches Aquinnah is famous for. Updated, bright ,cl ...
From $512 per night (USD)VRBO
From $487 per night (USD)VRBO
Edgartown convenience to beach, restaurants, shopping and public transportation.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in Edgartown, this apartment is a dream. With a daybed with two twin beds and a Queen sleigh bed. Fits 4 very co ...
From $487 per night (USD)VRBO
From $2066 per night (USD)VRBO
Spacious, Family-Friendly Edgartown Home – 3BR, Sleeps 14, Renovated in 2025
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 14
Spacious & Family-Friendly Edgartown Retreat – Fully Renovated in 2025 Welcome to your perfect Martha’s Vineyard getawa ...
From $2066 per night (USD)VRBO
From $4079 per night (USD)VRBO
Chilmark Luxury | Quansoo Beach Access-4BR
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover privacy and coastal charm at this exceptional 7.25-acre rental in Chilmark. Enjoy exclusive access to Quansoo B ...
From $4079 per night (USD)VRBO
From $405 per night (USD)VRBO
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Dogs Welcome w/ Fee | Beach Across Street | Postcard-Worthy Sunsets Easy island living awaits at this 3-bedroom, 1-bath ...
From $405 per night (USD)VRBO
From $239 per night (USD)VRBO
Walk to Beach & Lighthouse: Oak Bluffs Studio!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Pets Welcome w/ Fee | Solo Getaway or Couple's Retreat Island charm meets laid-back comfort at this 1-bathroom studio i ...
From $239 per night (USD)VRBO
From $1078 per night (USD)VRBO
Private house with jetted tub, deck, grill, central AC and large yard
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Family Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1078 per night (USD)VRBO
From $429 per night (USD)Expedia
Private suite with roof deck, near golf, bus stop, shops, and trails
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Garage Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $429 per night (USD)Expedia
From $955 per night (USD)VRBO
Charming, Victorian in East Chop
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relax with the whole family at this peaceful place to stay. Ideally located in East Chop, in walking distance to the B ...
From $955 per night (USD)VRBO
Click For PricingExpedia
Best Waterfront Views on Martha's Vineyard
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
One of a kind. Beachfront & Lakefront. Truly Spectacular! No better views on Martha's Vineyard. Private beach. Perfect f ...
Click For PricingExpedia
From $666 per night (USD)VRBO
Walk to Beach Spacious Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to our vineyard home, a charming haven nestled on 1/3 acre of land within steps to the center of town. This retre ...
From $666 per night (USD)VRBO
From $776 per night (USD)Expedia
Spacious house with private yard, firepit - option to rent car
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
3 Sisters Vineyard Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $776 per night (USD)Expedia
Click For PricingVRBO
3-bedroom townhome in charming Edgartown with WiFi, AC. Start your vacation now
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this 3-bedroom Edgartown retreat. This fabulous townhome boasts 2 queen beds and 1 full bed, pe ...
Click For PricingVRBO
From $1374 per night (USD)VRBO
Chilmark 1-bedroom Bunk house, WiFi, AC. Private Beach, Pets. No kitchen
- Bedrooms:
- 0
- Bathrooms:
- 1
- Sleeps:
- 3
Your cozy retreat in Chilmark with 1 bedroom featuring 3 comfortable twin beds upstairs in the loft. This charming house ...
From $1374 per night (USD)VRBO
From $3463 per night (USD)VRBO
Chilmark 4-bedroom house with WiFi, AC. Private South Shore Beach + Pond, Pets.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Chilmark is waiting for you at this 4-bedroom house. Step into this enchanting retreat with 1 king bed, 2 queen beds, an ...
From $3463 per night (USD)VRBO
From $5969 per night (USD)VRBO
7-Bed Rooms, Modern Main House, 1000 ft private beach, AC, Fast WiFi, Smart TV
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This stylish place to stay is perfect for a family getaway. Ultra modern 2 Bedroom, 2 full baths, 2 half baths, outdoor ...
From $5969 per night (USD)VRBO
From $5891 per night (USD)VRBO
2 BR, Modern Main House, private beach, AC, Wifi, Modern Luxury, Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This stylish place to stay is perfect for a romantic getaway. Ultra modern 2 Bedroom, 2 full baths, 2 half baths, outdoo ...
From $5891 per night (USD)VRBO
From $1132 per night (USD)Expedia
Wishing Well Oak Bluffs: 4-bedroom house with WiFi, AC - Close to Beach and Town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Consider this house your home away from home while you visit Oak Bluffs. With 4 charming bedrooms including a queen bed, ...
From $1132 per night (USD)Expedia
From $1068 per night (USD)VRBO
Serene private home w/ large deck & yard on conservation land
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
The Big Easy Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $1068 per night (USD)VRBO
From $526 per night (USD)Expedia
Oasis in downtown Oak Bluffs: 2 x King BR Condo, AC & Prime Location, sleeps 6\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 'Whale Tail', one of the most iconic and talked-about properties in Oak Bluffs! Located directly above Vineya ...
From $526 per night (USD)Expedia
From $850 per night (USD)VRBO
Classic Cape & Bunk House Nearby Downtown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This house is the perfect home away from home for your Vineyard holiday. The sitting & dining areas with the fully equi ...
From $850 per night (USD)VRBO
From $269 per night (USD)VRBO
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Pet Friendly w/ Fee | BBQ Ready | Outdoor Shower Seeking a relaxing Martha’s Vineyard escape? Look no further than this ...
From $269 per night (USD)VRBO
From $1977 per night (USD)VRBO
Fantastic Waterfront Private Beach & Dock on West Chop
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy everything you love about the Vineyard staying in this updated 4 bedroom house on the outer Vineyard Haven harbor. ...
From $1977 per night (USD)VRBO
From $658 per night (USD)Expedia
Charming 4-bedroom home in marvelous Tisbury walking distance to shops and ferry
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to Lake Street Haven, a beautifully decorated 4 bedroom, 3 bathroom private home located in the heart of Vineyard ...
From $658 per night (USD)Expedia
From $1117 per night (USD)VRBO
Modern Saltbox in Edgartown Village
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Gorgeous, coastal chic decor provide comfort in this modern 4 bedroom home only 5 blocks to Edgartown Village and 2.5 mi ...
From $1117 per night (USD)VRBO
From $475 per night (USD)Expedia
Spacious Woods Hole Beach Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious Woods Hole Beach Retreat Discover a serene blend of wooded tranquility and coastal charm at our spacious retre ...
From $475 per night (USD)Expedia
From $571 per night (USD)VRBO
Peaceful Island Getaway with Pool and Exclusive Beach Pass
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your Island Retreat on Martha's Vineyard! Nestled on a quiet dirt road in West Tisbury on nearly 2 acres, th ...
From $571 per night (USD)VRBO
From $586 per night (USD)VRBO
2-bedroom home with Pool and Tennis/Pickleball Court
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The guest house is part of a larger property (ID# 748468) and is available for exclusive rental (i.e., the main house re ...
From $586 per night (USD)VRBO
From $1994 per night (USD)VRBO
Soothing 4-bedroom house with a built full yard andAC in charming Tisbury
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This 4-bedroom house in Tisbury is perfect for your escape. With 1 king bed, 2 queen beds, 2 twin bed, and 2 futon, ther ...
From $1994 per night (USD)VRBO
From $838 per night (USD)Expedia
Charming Harborside hotel suite in enchanting Edgartown with AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the beauty of Edgartown from this 1-bedroom hotel suite. The room features a welcoming queen bed, perfect for a ...
From $838 per night (USD)Expedia
From $960 per night (USD)VRBO
Updated cozy home, tranquil neighborhood yet close to everything in Edgartown!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Warm and cozy, tastefully decorated, post and beam three bedroom Edgartown home close to Morning Glory Farm, with a shor ...
From $960 per night (USD)VRBO
From $1052 per night (USD)Expedia
Spacious 5-bedroom house with AC - near downtown Tisbury
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Serene & Spacious Retreat in Tisbury – Perfect for Your Getaway! Discover the charm and tranquility of this beautiful 5 ...
From $1052 per night (USD)Expedia
From $5940 per night (USD)VRBO
2 BR, Modern Main House, 1000 feet of private beach, AC, WiFi, Gym
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This stylish place to stay is perfect for a romantic getaway. Ultra modern 2 Bedroom, 2 full baths, 2 half baths, outdoo ...
From $5940 per night (USD)VRBO
From $688 per night (USD)VRBO
Centrally-located 3-bedroom house in Oak Bluffs with Expansive Yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Updated Cape in a quiet neighborhood is steps from the State forest and it's miles of bike paths. Ten minutes to Edgarto ...
From $688 per night (USD)VRBO
From $666 per night (USD)VRBO
4-bedroom house in Tisbury for a relaxing getaway - newly renovated
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Discover the beauty of Tisbury from this 4-bedroom house. Just a 5 minute walk to a small family beach with gorgeous sun ...
From $666 per night (USD)VRBO
From $2427 per night (USD)VRBO
Luxury Property with Sweeping Views & Private Beach in Oak Bluffs
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Set back off a bluff with expansive views of Nantucket Sound and beyond to Chappy is this sophisticated waterfront home ...
From $2427 per night (USD)VRBO
From $4282 per night (USD)VRBO
Luxury Living in Downtown Edgartown w/ Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This 4BR home is located in a quiet area of Downtown Edgartown just one block from Main Street. Enjoy the heate ...
From $4282 per night (USD)VRBO
From $1303 per night (USD)VRBO
Shady Pines - Pet Friendly Rolling Ranch Near Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Ideally located just one mile from downtown Oak Bluffs, this newly updated home is tucked away on a quiet stree ...
From $1303 per night (USD)VRBO
From $780 per night (USD)VRBO
3BR Coastal Retreat in Quiet Edgartown Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: Escape to this 3BR retreat nestled in a quiet Edgartown neighborhood with tennis/pickleball court and a walking ...
From $780 per night (USD)VRBO
From $1896 per night (USD)VRBO
Edgartown Compound with Pool & Guest Cottage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: This Edgartown compound includes a main house, guest house and heated pool, all within blocks of downtown. The ...
From $1896 per night (USD)VRBO
From $558 per night (USD)VRBO
Beautifully appointed Long Point Beach Retreat-West Tisbury-4 bedroom, 2.5 bath.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Less than 1 mile from Long Point Beach in West Tisbury, Summer Dream Cottage is an absolute jewel of a spot for your Mar ...
From $558 per night (USD)VRBO
From $1481 per night (USD)VRBO
Shells + Swells: 3BR South Beach Home in Katama
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to Shells + Swells, a charming three-bedroom South Beach home in Katama. This delightful house offers a ...
From $1481 per night (USD)VRBO