search location
Travel Dates:
Reset Dates
1,000 Rentals In Dukes Area
United States
Massachusetts
Dukes Area
Filters
Guests
Guests
1
2
3
4
5
6
7
8+
Price
Per Night:
Amenities
Pool
Internet
Washer
Fishing
FirePlace
Wheelchair Access
Non Smoking
Yard
TV
Balcony
Patio
Parking
AC
Microwave
No Pets
Jacuzzi
Pet Allowed
Dishwasher
Kitchen
Sauna
Crib
Smoking Allowed
Grill
Chappaquiddick Cozy 2 Bedroom, inquire about Spring 2024
2
1.0
6
Edgartown Massachusetts Cottage
From $247 per night
(USD)
Updated 2 Bed 2 Bath Condo with Tennis Courts
2
2.0
4
Edgartown Massachusetts Private vacation home
From $283 per night
(USD)
Family Home That Is Walking Distance To Town and Ferry
4
2.0
8
Vineyard Haven Massachusetts Private vacation home
From $366 per night
(USD)
A Charming Vineyard Cottage Just Off the Pond
3
3.0
7
Edgartown Massachusetts Cottage
From $500 per night
(USD)
1 WEEK LEFT! Lambert's Cove Beach Pass\/Close to Bike paths & Airport Market!!!
4
3.0
8
West Tisbury Massachusetts Private vacation home
From $571 per night
(USD)
Oceanfront 2-story home with guest house & private beach near downtown Edgartown
5
5.0
10
Edgartown Massachusetts Private vacation home
From $1455 per night
(USD)
FerryAvail-Family Delight MV\/Katama\/Edgartown-7 ductless A\/C airhandlers 2+Baths
4
4.0
11
Edgartown Massachusetts Private vacation home
From $880 per night
(USD)
Welcome to The “SUMMER WIND” House! 5-Minutes to the Beach!
5
3.0
10
Oak Bluffs Massachusetts Private vacation home
From $1000 per night
(USD)
Hidden Katama Gem with a Beautiful Backyard
3
2.0
6
Edgartown Massachusetts Private vacation home
Click For Pricing
Rest, Relax & Renew at this Newly Renovated Villa with New Pool!
4
3.0
8
Oak Bluffs Massachusetts Private vacation home
From $1592 per night
(USD)
WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!
4
4.0
16
Edgartown Massachusetts Private vacation home
From $2655 per night
(USD)
Walk your way into Vineyard Haven from Walker Way!
3
3.0
6
Tisbury Massachusetts Private vacation home
From $338 per night
(USD)
Private Beach Waterfront Oak-Bluffs Family Cottage
4
2.0
7
Oak Bluffs Massachusetts Cottage
From $1040 per night
(USD)
Waterfront condo with scenic views of Vineyard Haven harbor and beyond
1
1.0
4
Tisbury Massachusetts Condo
From $345 per night
(USD)
Secluded West Tisbury Retreat. Surrounded by Acres of Conservation Trails.
2
2.0
6
West Tisbury Massachusetts Private vacation home
From $261 per night
(USD)
Humble Abode \/Charming Cottage Near Long point Beach
3
2.0
6
West Tisbury Massachusetts Private vacation home
From $513 per night
(USD)
Private and quaint cabin-style home w\/ wrap-around porch - small dogs OK
2
1.0
4
Vineyard Haven Massachusetts Private vacation home
Click For Pricing
Swim And Sunsets At The Lagoon! Conveniently Located 2 Miles From Town!
3
3.0
6
Oak Bluffs Massachusetts Private vacation home
Click For Pricing
Waterfront Getaway With Beautiful Views Of Sengekontacket Pond
3
3.0
6
Edgartown Massachusetts Private vacation home
From $893 per night
(USD)
AMENITIES GALORE IN OAK BLUFFS PRIVATE COMMUNITY, DOCK, TENNIS, CENTRAL AC
5
3.0
14
Oak Bluffs Massachusetts Private vacation home
From $783 per night
(USD)
Bike to the Beach, Bike to Town
3
3.0
8
Edgartown Massachusetts Private vacation home
From $450 per night
(USD)
Ferry Tickets Available! Charming/Pet Friendly Cottage in Edgartown
3
2.0
6
Edgartown Massachusetts Cottage
From $550 per night
(USD)
Katama Luxury - 5+ BR home w\/ Heated Pool near The Field Club
5
6.0
14
Edgartown Massachusetts Private vacation home
From $764 per night
(USD)
Family-Friendly Tisbury Escape - Walk to Town
5
2.0
8
Tisbury Massachusetts Private vacation home
From $252 per night
(USD)
Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews
3
3.0
8
Vineyard Haven Massachusetts Private vacation home
From $650 per night
(USD)
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
5
3.0
9
Oak Bluffs Massachusetts Private vacation home
From $650 per night
(USD)
Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.
3
3.0
6
Oak Bluffs Massachusetts Private vacation home
From $742 per night
(USD)
EDGARTOWN PRIVATE HOME CLOSE TO TOWN AND BEACH. NEW KITCHEN FOR 2023-24
3
2.0
10
Edgartown Massachusetts Private vacation home
From $788 per night
(USD)
Airy, Quiet Vacation Rental Home, pool, tennis, FERRY TIX on MV
3
3.0
8
West Tisbury Massachusetts Private vacation home
From $625 per night
(USD)
Dog-Friendly Home w\/Amazing Fenced-In Yards, Private Washer\/Dryer, Free WiFi
3
2.0
6
Oak Bluffs Massachusetts Private vacation home
From $667 per night
(USD)
Walk to Edgartown Wharf - Upgraded Vineyard Home with A\/C and Outdoor Area
4
3.0
8
Edgartown Massachusetts Private vacation home
From $650 per night
(USD)
Historic Oak Bluffs home, short walk to town, beach, and harbor.
3
3.0
6
Oak Bluffs Massachusetts Private vacation home
From $250 per night
(USD)
Private Chappaquiddick Retreat with Large Screened in Porch. Minutes from Beach!
3
3.0
7
Edgartown Massachusetts Private vacation home
From $789 per night
(USD)
West Tisbury Wooded Summer Retreat
3
2.0
6
West Tisbury Massachusetts Private vacation home
From $450 per night
(USD)
Split-Level, Family-Friendly Home w\/ a Rear Deck, Gas Grill, Free WiFi, & W\/D
3
2.0
6
Edgartown Massachusetts Private vacation home
From $343 per night
(USD)
Beautiful Lambert Cove House with panoramic water views
4
4.0
8
West Tisbury Massachusetts Private vacation home
From $592 per night
(USD)
A Vineyard Home Perfect For Family Gatherings
4
2.0
8
Vineyard Haven Massachusetts Private vacation home
From $454 per night
(USD)
Cottage w\/ water views from front yard, central ac & fireplace - dog ok
2
1.0
4
Vineyard Haven Massachusetts Private vacation home
From $795 per night
(USD)
Vineyard Gem: < 2 Mi to Beach & Oak Bluffs!
3
3.0
10
Oak Bluffs Massachusetts Private vacation home
From $428 per night
(USD)
Chappy Summer Cabin!
2
2.0
4
Edgartown Massachusetts Cottage
Click For Pricing
Family & dog friendly; walk to beach, cliff, town, ferries, all bedrooms w\/AC
3
2.0
7
Oak Bluffs Massachusetts Private vacation home
From $490 per night
(USD)
Spacious Home with Beautiful Yard, Deck, Free WiFi, W\/D, & Outdoor Shower
4
3.0
8
West Tisbury Massachusetts Private vacation home
From $119 per night
(USD)
Charming, Dog-Friendly House with Lots of Entertainment & Gourmet Kitchen
3
2.0
6
Oak Bluffs Massachusetts Private vacation home
From $634 per night
(USD)
Historic Home with Gorgeous Antiques & Mondern Conveniences
4
2.0
8
Oak Bluffs Massachusetts Private vacation home
From $537 per night
(USD)
Cozy cottage 3\/4 mile from Oak Bluffs harbor
3
2.0
6
Oak Bluffs Massachusetts Private vacation home
From $270 per night
(USD)
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
2
2.0
4
Oak Bluffs Massachusetts Condo
From $542 per night
(USD)
Uniquely designed island retreat with fast WiFi & private W\/D - dogs welcome
1
1.0
4
West Tisbury Massachusetts Private vacation home
From $463 per night
(USD)
Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches
2
1.0
4
Oak Bluffs Massachusetts Private vacation home
From $260 per night
(USD)
Large Deck & Yard - Steps from Downtown, Walk to Beach
3
3.0
6
Edgartown Massachusetts Private vacation home
From $596 per night
(USD)
New Construction with Patio & Yard - Walk to the Ferry, Downtown & Beaches
4
3.0
10
Oak Bluffs Massachusetts Private vacation home
From $769 per night
(USD)
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
4
2.0
8
Chilmark Massachusetts Private vacation home
From $282 per night
(USD)
Charming home away from home near lagoon pond w\/ boat launch
3
2.0
7
Oak Bluffs Massachusetts Private vacation home
From $179 per night
(USD)
Martha's Vineyard Apt ~ 1 Mile to Inkwell Beach!
2
1.0
6
Vineyard Haven Massachusetts Apartment
From $453 per night
(USD)
Quaint,,,Quiet..up island feel yet a short walk to to , x ,, z wn and harbor
3
3.0
7
Oak Bluffs Massachusetts Private vacation home
From $383 per night
(USD)
Ground-Floor Apartment with Screened Porch, Yard, Grill & WiFi - Dogs Welcome
2
1.0
4
Oak Bluffs Massachusetts Apartment
Click For Pricing
Cozy Martha’s Vineyard Getaway w\/ Waterfront Deck!
2
1.0
6
Vineyard Haven Massachusetts Apartment
Click For Pricing
Beautiful downtown Oak Bluffs!
3
2.0
6
Oak Bluffs Massachusetts Private vacation home
From $700 per night
(USD)
Perfect Family Home- Oak Bluffs, Martha's Vineyard
3
4.0
10
Oak Bluffs Massachusetts Private vacation home
From $542 per night
(USD)
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
1
1.0
4
Oak Bluffs Massachusetts Apartment
From $350 per night
(USD)
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
1
1.0
4
Oak Bluffs Massachusetts Apartment
From $350 per night
(USD)
Peaceful Edgartown Retreat - Clean, Renovated, Central Location
3
3.0
8
Edgartown Massachusetts Private vacation home
From $433 per night
(USD)
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
3
2.0
8
Oak Bluffs Massachusetts Cottage
From $402 per night
(USD)
Peaceful Oak Bluffs home
3
2.0
6
Oak Bluffs Massachusetts Private vacation home
From $357 per night
(USD)
Charming Home with High-Speed WiFi, Washer\/Dryer, Furnished Deck, & Gas Grill
4
3.0
7
Oak Bluffs Massachusetts Private vacation home
From $288 per night
(USD)
Newly Renovated Apartment in the heart of Edgartown on the Bike Path!
1
1.0
4
Edgartown Massachusetts Apartment
From $354 per night
(USD)
Walking-distance to town, shops, restaurants & ferry!
2
1.0
4
Tisbury Massachusetts Apartment
From $799 per night
(USD)
#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home, walk to town, ferry, beach
1
2.0
2
Oak Bluffs Massachusetts Private vacation home
From $541 per night
(USD)
Stunning, Classic Renovated Greek Revival - few mins Walk to Main St & VH Ferry
4
3.0
10
Vineyard Haven Massachusetts Private vacation home
From $899 per night
(USD)
Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel
4
2.0
8
Oak Bluffs Massachusetts Private vacation home
From $641 per night
(USD)
Vintage Victorian with Nantucket Sound Views & AC | Walk 100 Steps to Beach
4
3.0
10
Oak Bluffs Massachusetts Private vacation home
Click For Pricing
New Build | Private Locale on 16 Acres | Central AC & Outdoor Shower
1
1.0
4
Edgartown Massachusetts Private vacation home
From $1016 per night
(USD)
Charming forest retreat by the beach with grill, deck, & sprawling yard
4
3.0
10
West Tisbury Massachusetts Private vacation home
From $352 per night
(USD)
Classic Oak Bluffs Beach House | Excellent Harbor Views | Near Shops & Dining
5
1.0
8
Oak Bluffs Massachusetts Private vacation home
From $744 per night
(USD)
Charming Home with Deck, Screened Porch, Private Balcony, Near Beaches
3
2.0
6
Edgartown Massachusetts Private vacation home
From $779 per night
(USD)
Spacious New-Build w\/ Gourmet Kitchen & Large Yard - Near Beach & Ferry
4
4.0
8
Vineyard Haven Massachusetts Private vacation home
From $386 per night
(USD)
Oak Bluffs Bliss | Beautiful Getaway | Home Theater & Fireplaces
5
4.0
10
Oak Bluffs Massachusetts Private vacation home
From $1154 per night
(USD)
Modern home in a great location with large yard & private patio
3
2.0
6
West Tisbury Massachusetts Private vacation home
From $211 per night
(USD)
Dog-friendly secluded island gem with deck, hot tub, patio, & great views
4
3.0
8
Edgartown Massachusetts Private vacation home
From $1859 per night
(USD)
Coastal condo with pool, tennis courts & home comforts - close to beach
1
2.0
6
Oak Bluffs Massachusetts Condo
From $303 per night
(USD)
Dog-friendly first-floor seaside cottage with pool & tennis courts
1
1.0
4
Oak Bluffs Massachusetts Condo
From $465 per night
(USD)
Cute condo with pool & tennis - close to golf & the beach
2
1.0
4
Oak Bluffs Massachusetts Condo
From $288 per night
(USD)
Charming suite with pool & tennis courts - 1\/2 mile to the beach
1
2.0
6
Oak Bluffs Massachusetts Condo
From $316 per night
(USD)
Dog-friendly townhouse with pool & tennis - easy walk to the beach
2
2.0
6
Oak Bluffs Massachusetts Private vacation home
From $392 per night
(USD)
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
2
2.0
4
Oak Bluffs Massachusetts Private vacation home
From $240 per night
(USD)
Deluxe townhouse with pool & tennis courts - half-mile to the beach
2
2.0
4
Oak Bluffs Massachusetts Private vacation home
From $402 per night
(USD)
Sunny coastal retreat with pool & tennis - 1\/2 mile to beach
2
2.0
4
Oak Bluffs Massachusetts Private vacation home
From $365 per night
(USD)
Cozy seaside escape with on-site tennis, pool & prime location
1
1.0
4
Oak Bluffs Massachusetts Condo
From $402 per night
(USD)
Stylish townhouse 1\/2 mile from the beach with tennis courts & pool
2
2.0
6
Oak Bluffs Massachusetts Private vacation home
From $369 per night
(USD)
Dog-friendly suite with pool & tennis - golf & beach nearby
1
2.0
5
Oak Bluffs Massachusetts Condo
From $306 per night
(USD)
Coastal getaway 1\/2 mile from beach with pool & tennis courts - dog-friendly
1
2.0
6
Oak Bluffs Massachusetts Condo
From $328 per night
(USD)
Lovely retreat 1\/2 mile from the beach with pool & 3 tennis courts
1
2.0
6
Oak Bluffs Massachusetts Condo
From $373 per night
(USD)
Lovely condo suite, close to golfing & the beach with pool & home comforts
1
2.0
4
Oak Bluffs Massachusetts Condo
From $305 per night
(USD)
Sunny, dog-friendly suite with tennis & pool - close to golf & beach
1
2.0
6
Oak Bluffs Massachusetts Condo
From $300 per night
(USD)
Charming condo with pool & resort amenities - close to the beach
1
2.0
6
Oak Bluffs Massachusetts Condo
From $366 per night
(USD)
Dog-friendly condo with pool - explore the parks & hit the beach
1
1.0
4
Oak Bluffs Massachusetts Condo
From $361 per night
(USD)
Corner condo with tennis & swimming pool - close to beaches, golf & town
1
2.0
6
Oak Bluffs Massachusetts Condo
From $366 per night
(USD)
Comfortable, dog-friendly condo with pool & tennis - perfect location
2
1.0
4
Oak Bluffs Massachusetts Condo
From $283 per night
(USD)
Comfortable townhouse close to town & the beach with outdoor pool & tennis
2
2.0
6
Oak Bluffs Massachusetts Private vacation home
From $400 per night
(USD)
Dog-friendly condo with pool & tennis courts - golf & beach nearby
2
2.0
6
Oak Bluffs Massachusetts Private vacation home
From $363 per night
(USD)
Lovely townhouse with deck, pool & tennis - walk to the beach
2
2.0
6
Oak Bluffs Massachusetts Private vacation home
From $423 per night
(USD)
Load More Results