Dukes Area, Massachusetts Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Dukes Area, Massachusetts on RentalSaver.com!

Dukes Area Rentals

From $1255 per night (USD)
VRBO
Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs!
Bedrooms:
2
Bathrooms:
7
Sleeps:
16
Fantastic home available from May to October. Seven Bedrooms, one den with pull out couch, two bathrooms and a dreamy o ...
From $1255 per night (USD)
VRBO
From $838 per night (USD)
VRBO
Edgartown Cottage By The Pond
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Be the first to stay in this recently renovated cottage which is centrally located to everything the island has to offer ...
From $838 per night (USD)
VRBO
From $658 per night (USD)
VRBO
Perfect location! Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This lovely, in-town, first-floor apartment is in a renovated 1800's historic Oak Bluffs cottage with a fenced in landsc ...
From $658 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Fully Renovated & Spacious home within walking distance of Oak Bluffs / Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly renovated three-level home with three bedrooms and two bathrooms within walking distance to the heart of Downtown ...
From $428 per night (USD)
VRBO
From $1117 per night (USD)
VRBO
Ocean sounds at this Oyster Pond retreat pastoral view and short walk to pond
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
"The Gathering Place" is a recently renovated four bedroom two full bathroom home with two living areas, dedicated offic ...
From $1117 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Cozy New TimberFrame Vineyard Haven!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Modern meets Vintage in Vineyard Haven! Brand New Timberframe Custom Designed by Local Boat Builder. One of a Kind Gues ...
From $495 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Central 2nd-floor apartment with propane stove, grill, W/D, & great location
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Main Street Upper Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $420 per night (USD)
VRBO
From $4074 per night (USD)
VRBO
CHILMARK WATERFRONT WITH PRIVATE DOCK
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Chilmark waterfront rental home with a dock located on Quitsa Pond with views across Quitsa and Menemsha ponds out to th ...
From $4074 per night (USD)
VRBO
From $4771 per night (USD)
VRBO
Stunning private family home - spectacular sunsets
Bedrooms:
6
Bathrooms:
8
Sleeps:
16
Our family home is a 4-acre waterfront paradise with wonderful sunsets. The private location sits between a large wooded ...
From $4771 per night (USD)
VRBO
From $211 per night (USD)
VRBO
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
July and August: Turnover day is generally Friday. This lovely, in-town, impeccably renovated 1800's historic Oak Bluff ...
From $211 per night (USD)
VRBO
From $681 per night (USD)
VRBO
Labor Day September escape with Car Ferry tickets Aug 30th to Sept 6th!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled in woods adjacent to conservation trails, and Coveted Lambert's cove beach is just 7min drive away. Cozy home wi ...
From $681 per night (USD)
VRBO
From $403 per night (USD)
VRBO
In-Town Classic Cape
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
POINT B EXCLUSIVE - This In-Town Classic Cape has just been renovated and reimagined throughout with new Kitchen and Bat ...
From $403 per night (USD)
VRBO
From $834 per night (USD)
VRBO
Classic Saltbox Cape In The Heart Of Katama
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
POINT B EXCLUSIVE - This Classic Saltbox Cape sits back in a quiet neighborhood in the heart of Katama. The first floor ...
From $834 per night (USD)
VRBO
From $374 per night (USD)
Expedia
Perfectly located duplex with comfy layout & beach gear - steps from Main Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Island Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $374 per night (USD)
Expedia
From $1593 per night (USD)
VRBO
Morse Ferry House - Deluxe Waterfront home on Edgartown Harbor w lighthouse view
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
You are right on the water in this exquisite waterfront property. Watch the action from your own private deck. Featured ...
From $1593 per night (USD)
VRBO
From $1597 per night (USD)
VRBO
Morse Lighthouse-Waterfront home in Edgartown
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
You are right on the water in this exquisite waterfront property. Watch the action from your own private deck. Featured ...
From $1597 per night (USD)
VRBO
Click For Pricing
VRBO
Beautiful Chilmark - Blueberry Ridge - August!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This property is available August 5-19, 2023. Located just off North Road in Chilmark, this Blueberry Ridge guest house ...
Click For Pricing
VRBO
From $449 per night (USD)
VRBO
Vineyard Haven Guest Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Classic Vineyard Haven cottage, in the heart of the village, just a few blocks from the ferry. We love this cottage for ...
From $449 per night (USD)
VRBO
From $3686 per night (USD)
VRBO
Harbor Front in Vineyard Haven! Brand New Construction - seconds from Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover a newly constructed 3-bed, 2.5-bath rental with captivating views of Vineyard Haven Harbor. Adjacent to the Ste ...
From $3686 per night (USD)
VRBO
From $782 per night (USD)
Expedia
Fernbank Hideaway | House in West Tisbury near up-island beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Fernbank Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $782 per night (USD)
Expedia
From $1136 per night (USD)
VRBO
Spacious and gracious architect designed home on 3 acres off Middle Road.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Our home is off Middle Road in Chilmark. It features a chef's kitchen with convectionoven, screen porch, roof deck, out ...
From $1136 per night (USD)
VRBO
From $667 per night (USD)
Expedia
Vineyard Haven Oasis!-Get 1 Free Boat Reservation for Car!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Vineyard Haven Oasis is fully equipped. It’s Centrally Located to Downtown Vineyard Haven, Island attractions, res ...
From $667 per night (USD)
Expedia
From $1180 per night (USD)
VRBO
Brand New!!!!!Guest House in Edgartown, MA
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy a stylish experience at this centrally-located place. All Renovated 2 bedrooms/1 bathrooms house with a lovely kit ...
From $1180 per night (USD)
VRBO
$Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs\n$
From $1234 per night (USD)
Expedia
Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs\n
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Retreat to Martha's Vineyard in a modern ranch style vacation home with a heated pool tucked on 1.5 acres of landscaped ...
From $1234 per night (USD)
Expedia
From $194 per night (USD)
VRBO
Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Nana's Backyard Treehouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $194 per night (USD)
VRBO
From $503 per night (USD)
VRBO
Quiet Edgartown vacation home - 10 minutes from door to beach chair!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This home is equipped with everything you need for a day on South Beach, State Beach or nearby Long Point. Perfect for a ...
From $503 per night (USD)
VRBO
Click For Pricing
VRBO
Martha's Vineyard Home w/ Deck < 1 Mi to Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the beauty of Martha’s Vineyard when you stay at this charming 3-bedroom, 2.5-bathroom vacation rental! Situate ...
Click For Pricing
VRBO
$Edgartown Village Home w/ Pool. \n4bdrm / 3.5bth$
From $1254 per night (USD)
Expedia
Edgartown Village Home w/ Pool. \n4bdrm / 3.5bth
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Fully renovated in 2020, this 4 bedroom / 3.5 bath cottage is the perfect spot for fun and relaxation. 0.4 miles to Main ...
From $1254 per night (USD)
Expedia
From $2402 per night (USD)
VRBO
Beautiful Newly Constructed Home Walking Distance from Downtown Vineyard Haven
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Welcome to this beautiful newly constructed home, conveniently located within walking distance from the Steamship Author ...
From $2402 per night (USD)
VRBO
From $740 per night (USD)
VRBO
Renovated colonial in private community
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
**Ferry tickets available 7/13-7/20; 7/20-7/27** Spacious Colonial in private Edgartown community. Ideal for 1-2 famil ...
From $740 per night (USD)
VRBO
From $638 per night (USD)
VRBO
Bright Modern House AC 3full baths, 3+ bedrooms, 2 balconies, deck & parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Bright air conditioned house has common space living TV room, dining and kitchen together. 1st floor has 1 bedroom with ...
From $638 per night (USD)
VRBO
From $379 per night (USD)
Expedia
Charming 2-story house near the beach with inviting deck, large yard & canoe
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Nana’s Treehouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $379 per night (USD)
Expedia
From $491 per night (USD)
VRBO
Nana’s Treehouse | House with spacious deck, grills, outdoor shower & W/D
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Nana’s Big Treehouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $491 per night (USD)
VRBO
From $782 per night (USD)
VRBO
Pet-Friendly Historic Chilmark House
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Renovated historic house (1870). Large living room/dining area. 4 bedrooms sleep 8 plus sofa sleepers. 3 full bathrooms. ...
From $782 per night (USD)
VRBO
From $464 per night (USD)
VRBO
3-BR Oak Bluffs Escape - Quick Trip to Towns & Beaches!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape and exhale in this bright, airy 3-bedroom, 2.5-bathroom retreat that sleeps up to 7. Centrally located between Oa ...
From $464 per night (USD)
VRBO
Click For Pricing
Expedia
House in the woods in Chiomark
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
3 bedroom, 3 bath house on 11 acres in Chilmark outdoor grill, dining. large open space large living room, dining room.s ...
Click For Pricing
Expedia
From $1728 per night (USD)
VRBO
Tranquil 5 BR House, Heated Saltwater Pool Near Downtown Edgartown
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
If you are looking for the quintessential Martha’s Vineyard beach house -look no further. This 5 bedroom+ house is locat ...
From $1728 per night (USD)
VRBO
From $1672 per night (USD)
VRBO
Daniels House is your next vacation home in Oak Bluffs.
Bedrooms:
6
Bathrooms:
9
Sleeps:
18
Breath taking views from this newly restored quintessential 1899 Oak Bluffs Cottage style home. It is equipped with 9 la ...
From $1672 per night (USD)
VRBO
From $1058 per night (USD)
VRBO
Brand New 4 Bedroom Home in Katama
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Welcome to Your Perfect Katama Coastal Retreat. This newly fully renovated Classic Cape Cod-style gem in Edgartown is yo ...
From $1058 per night (USD)
VRBO
From $628 per night (USD)
Expedia
Hideaway At Meadow View Farm/Private Tennis Courts with Spacious Bedrooms
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This Martha’s Vineyard Hideaway is nestled in the desirable Meadow View Farms area of Oak Bluffs, and includes access to ...
From $628 per night (USD)
Expedia
From $1094 per night (USD)
VRBO
Cozy Family Home Centrally Located in West Tisbury
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Escape to your perfect Martha's Vineyard getaway at this beautifully renovated family home in West Tisbury. With four be ...
From $1094 per night (USD)
VRBO
From $243 per night (USD)
VRBO
Martha’s Vineyard studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Studio apartment on highly sought resort island of Martha’s Vineyard. 500 square feet with private entrance, bathroom, ...
From $243 per night (USD)
VRBO
From $732 per night (USD)
VRBO
Charming Oak Bluffs Retreat – Walk to Town, Harbor & More
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Just outside downtown Oak Bluffs, this 3-bedroom, 2.5-bath home features Central AC and an open layout ideal for gatheri ...
From $732 per night (USD)
VRBO
From $1099 per night (USD)
VRBO
Brand New Home in Vineyard Haven - Perfect Family Home Centrally Located on MV!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This BRAND NEW, recently built 4-bedroom, 3-bathroom home offers the perfect blend of comfort and convenience, situated ...
From $1099 per night (USD)
VRBO
From $582 per night (USD)
VRBO
Historical house with wraparound porch, modern updates, enclosed yard, & W/D
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Victorian by the Sea Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $582 per night (USD)
VRBO
From $742 per night (USD)
VRBO
Centrally located Oak Bluffs property next to Bike Path
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to our vacation rental in Oak Bluffs, Martha's Vineyard! Lovely home in the sought after Meadow View Farms commu ...
From $742 per night (USD)
VRBO
From $1243 per night (USD)
VRBO
Charming home with private hot tub, firepit, deck, grill, outdoor shower, AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Tiffany's Treasure Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1243 per night (USD)
VRBO
From $936 per night (USD)
VRBO
Oceanview East Chop Beach House - 4 Bed/2 Bath - 5 min walk to beach
Bedrooms:
1
Bathrooms:
4
Sleeps:
9
The perfect vacation awaits you at Frog Prince Cottage in beautiful East Chop, the finest neighborhood in Oak Bluffs. Ou ...
From $936 per night (USD)
VRBO
From $447 per night (USD)
VRBO
Spacious 4 BR Home, Steps to Lagoon, Minutes to Downtown Oak Bluffs and Beaches!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Spacious two-level four-bedroom house within steps to lagoon located in Oak Bluffs and within minutes (2 Miles) to Downt ...
From $447 per night (USD)
VRBO
From $708 per night (USD)
VRBO
Modern Farmhouse With Stylish Design In Edgartown
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
POINT B EXCLUSIVE - This newly built Modern Farmhouse has a fresh and stylish design throughout. The first-floor featur ...
From $708 per night (USD)
VRBO
From $480 per night (USD)
VRBO
Charming Martha's Vineyard retreat close to beaches & downtown - large yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Set Sail Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $480 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Gingerbread Dream Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $461 per night (USD)
Expedia
From $1165 per night (USD)
VRBO
Elegant In-Town Federal Home Newly Decorated
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This gorgeous single family 4 bedroom, 2 bath historical home was newly purchased and decorated in Spring 2011 and renov ...
From $1165 per night (USD)
VRBO
From $438 per night (USD)
VRBO
Heart of the village of Woods Hole!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
A historic home built in 1850 provides a true Cape Cod experience. The home is located in the heart of downtown Woods H ...
From $438 per night (USD)
VRBO
Click For Pricing
VRBO
Harbor View Suite at Harborside Inn in Edgartown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Harborside Inn is perfectly situated in Martha’s Vineyard with plenty of things to do within close walking distance ...
Click For Pricing
VRBO
$\nMV Vacation Rental$
From $686 per night (USD)
Expedia
\nMV Vacation Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to MV Vacation Rental! Our charming rental property features a loft upstairs with a comfortable queen bedroom, c ...
From $686 per night (USD)
Expedia
From $907 per night (USD)
VRBO
Spacious, Air-Conditioned Home Close to Beaches
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This beautiful three-story house is recently available for rentals again. With room to spread out for up to 10 guests, t ...
From $907 per night (USD)
VRBO
From $5215 per night (USD)
VRBO
Main house and a separate apartment with saltwater pool, spa, outdoor cooking!
Bedrooms:
6
Bathrooms:
7
Sleeps:
12
Forget your worries in this spacious and serene space. Tucked away, the brand new compound offers all amenities. Heated, ...
From $5215 per night (USD)
VRBO
From $884 per night (USD)
VRBO
Location , Location , Location ! Walking distance to the beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Bellavista at the Seaview. This oceanfront condo is a coveted two bedroom , two bathroom home that was comple ...
From $884 per night (USD)
VRBO
Click For Pricing
Expedia
Spacious home near the ferry & downtown with enclosed yard, games, & W/D
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The Ferry Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
Click For Pricing
Expedia
From $300 per night (USD)
VRBO
Cozy studio with AC,WiFi, full kitchen, private entry great for couples vacation
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Your Tisbury adventure begins at this tranquil studio. Nestled in a pleasant neighborhood, this welcoming retreat offers ...
From $300 per night (USD)
VRBO
From $726 per night (USD)
VRBO
Centrally located home in private neighborhood of Oak Bluffs.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax and unwind in this comfortable spacious 3 bedroom 2 bath open concept home in a quiet neighborhood. Enjoy your di ...
From $726 per night (USD)
VRBO
From $752 per night (USD)
VRBO
Katama Cape 5 minutes to South Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Close proximity to both South Beach and downtown Edgartown. Stroll to the Katama Airfield for a meal or a scenic plane r ...
From $752 per night (USD)
VRBO
From $1124 per night (USD)
VRBO
Spacious 5-bedroom house with AC and WiFi in brilliant Oak Bluffs
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Perched on a grassy hill, this majestic home has sweeping views of Oak Bluffs Harbor and is just minutes from East Chop ...
From $1124 per night (USD)
VRBO
Click For Pricing
VRBO
Amazing sunsets. Beautiful 3 bedroom home on 4 acres near Lamberts Cove Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy stunning sunsets from this beautiful home set on 4 quiet acres near Lambert's Cove Beach. Relax and unwind in this ...
Click For Pricing
VRBO
From $550 per night (USD)
VRBO
September 2025 Available! 6 Beds! Near Ocean Park, Inkwell, Ferry, Flying Horses
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
6 Bedrooms with incredible location will comfortably allow your family to vacation in the best part of Oak Bluffs. The l ...
From $550 per night (USD)
VRBO
From $572 per night (USD)
VRBO
Modern Family Home Walkable to Town
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to our Modern Private Vineyard retreat! Nestled in a tranquil neighborhood, this spacious two-story house offers ...
From $572 per night (USD)
VRBO
From $713 per night (USD)
Expedia
Family Getaway Walkable to Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our newly renovated cottage nestled in the peaceful town of Vineyard Haven. This delightful retreat features ...
From $713 per night (USD)
Expedia
From $1902 per night (USD)
VRBO
Private 14 Acre Waterfront Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfor ...
From $1902 per night (USD)
VRBO
From $503 per night (USD)
VRBO
Four bedroom 3 bathroom ranch located in Edgartown.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
*****Those summer vacation memories are waiting to be made here. Four bedroom 3 bathroom ranch located in Edgartown. M ...
From $503 per night (USD)
VRBO
From $2376 per night (USD)
VRBO
Gorgeous 7BR/6BA Ocean views Walk to Beach & Town - 10% off two week stay!
Bedrooms:
6
Bathrooms:
7
Sleeps:
10
Large Private Home formerly known as the SeaSpray Inn and featured on the reality television show "The Vineyard", this l ...
From $2376 per night (USD)
VRBO
From $1161 per night (USD)
Expedia
Katama Retreat W Pickle ball Court
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
NEWLY LISTED/ NEW REBUILD Located in Katama near Morning Glory Farm, South Beach and town, this 3 BD home w/private ass ...
From $1161 per night (USD)
Expedia
From $337 per night (USD)
VRBO
Contemporary cottage with outdoor shower infrared sauna 6 Min drive to the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
!3 bedroom 2 bathroom home in heart of chappaquidick island . Off the main road close to Mytoi garden , waque and dike ...
From $337 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Chilmark Guest House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $326 per night (USD)
Expedia
From $1174 per night (USD)
VRBO
Oak Bluff's Victorian Walk to Town & Beaches
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
About this space First floor has AC and hosts windowed living, dining, work space, kitchen and garden bedroom that sleep ...
From $1174 per night (USD)
VRBO
From $460 per night (USD)
Expedia
New 2 min from Circuit ave
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
* new for 2025: Gameroom with pool table and ping pong table. * Welcome to this beautifully renovated home, located wit ...
From $460 per night (USD)
Expedia
From $697 per night (USD)
VRBO
Country life in peaceful West Tisbury with pond near Lambert's Cove beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
OWNER WILL BE FLEXIBLE ON ENTRY AND DEPARTURE DATES IN ORDER TO INCREASE CHANCE OF GETTING FERRY TICKETS. MANY WEEKS AR ...
From $697 per night (USD)
VRBO
Click For Pricing
Expedia
5 Min Drive to Beach/Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy seclusion surrounded by woods on this private 16-acre location. This heavily landscaped house offers a furnished p ...
Click For Pricing
Expedia
From $816 per night (USD)
VRBO
Beautiful home, walk to beach, has AC. Long-term winter rental considered.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This spacious home is located in a private woodland, just a short walk to Lobsterville beach. The house is welcoming, we ...
From $816 per night (USD)
VRBO
From $740 per night (USD)
VRBO
Chappy Cottage designed for the vacationer. Patio, outdoor shower, grill
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
This charming Chappy Cottage was designed with the vacationer in mind. The home features two furnished decks to enjoy th ...
From $740 per night (USD)
VRBO
Click For Pricing
VRBO
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Charming Edgartown Retreat - Walk to Village and Beaches Nestled on a winding street, our three-bedroom top-floor unit ...
Click For Pricing
VRBO
Click For Pricing
Expedia
5 Minute Walk to Vineyard Haven Yacht Club and Town Beach at Owen Little Way!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover this spacious and conveniently located property which is just a 5 Minute Walk to Vineyard Haven Yacht Club an ...
Click For Pricing
Expedia
From $511 per night (USD)
VRBO
Charming cottage near the beach with a furnished deck, yard, & washer/dryer
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Birds of Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $511 per night (USD)
VRBO
From $811 per night (USD)
VRBO
Perfect Location for a Martha's Vineyard Vacation or Wedding. Pet Friendly!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Let the vacation or Vineyard wedding visit begin! Centrally located in Edgartown, near Morning Glory Farm and equal dist ...
From $811 per night (USD)
VRBO
From $6054 per night (USD)
VRBO
Casa Katama: Luxury Compound With Guest House And Pool
Bedrooms:
8
Bathrooms:
3
Sleeps:
16
POINT B EXCLUSIVE - This stunning Katama compound features a Main House with three levels of uniquely designed green liv ...
From $6054 per night (USD)
VRBO
From $1781 per night (USD)
VRBO
Waterview Farm Contemporary Island Home Walk to Beach and Farm Neck Golf Club
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Six bedroom, five and a half bath contemporary island home located in Waterview Farm with direct access to the beach on ...
From $1781 per night (USD)
VRBO
Click For Pricing
VRBO
Quaint and pristine home with private suites and baths.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to our home! We are a husband & wife interior decorator/contractor team, who've tastefully renovated our entire ...
Click For Pricing
VRBO
From $1165 per night (USD)
VRBO
Newly Renovated Charming West Tisbury Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Beautiful new renovation! Centrally located near Alley's General Store and the West Tisbury Library, enjoy easy access ...
From $1165 per night (USD)
VRBO
From $689 per night (USD)
VRBO
Secluded Cottage, West Tisbury, Lambert's Cove Beach Access
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Nestled in the woods of West Tisbury, this charming 2-bedroom +, 900 sq. ft. home, with additional sleeping loft, offers ...
From $689 per night (USD)
VRBO
From $1760 per night (USD)
Expedia
Country Farmhouse, Old Vineyard, Central AC, 2 King beds.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
About the house and Property: Old world charm, new world amenities. On the Massachusetts Historical Commission's regis ...
From $1760 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Quaint home across from bike paths with large furnished deck, grill, & W/D
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The C-Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $215 per night (USD)
VRBO
From $1189 per night (USD)
VRBO
Heart of Oak Bluffs - A Newly Renovated Gem, 5 Minute Walk to Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the perfect blend of location and luxury in this beautifully renovated charmer, centrally situated in Oak Bluff ...
From $1189 per night (USD)
VRBO
From $358 per night (USD)
VRBO
Serene Dog Friendly Island Retreat with A/C and Washer/Dryer
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Cormorant - Main House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $358 per night (USD)
VRBO
From $584 per night (USD)
Expedia
Walking to the beach. Bars and Restaurants.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Walking distance to the beach. 5 minutes away from downtown, steamship, ice cream, and restaurants. Lovely backyard with ...
From $584 per night (USD)
Expedia
From $682 per night (USD)
VRBO
Private island house close to trails with kayak, jetted tub, and deck
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Lookout Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $682 per night (USD)
VRBO
$Cozy History Resort\nLocated in the center of the city$
From $397 per night (USD)
Expedia
Cozy History Resort\nLocated in the center of the city
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Friendly and fun Environment. BBQ grills on the patio for those grill masters ready to whip up a mean steak. We have a b ...
From $397 per night (USD)
Expedia
From $397 per night (USD)
VRBO
Harbor Landing Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Are you ready to come and enjoy the fun and beautiful island on a budget, then look no further. Come by our beautiful hi ...
From $397 per night (USD)
VRBO
From $509 per night (USD)
Expedia
Harbor Landing Resort
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Looking to visit the vineyard on a budget, look no further. We provide a friendly, fun, sociable, budget and cost effici ...
From $509 per night (USD)
Expedia
From $869 per night (USD)
VRBO
Charming home near downtown & beach with patio, outdoor shower, grill, & W/D
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Blissful Island Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $869 per night (USD)
VRBO
From $726 per night (USD)
Expedia
Cozy vineyard cottage close to downtown with outdoor living space and amentiies.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
2 Decks, hot tub and close to everything. Has all new stainless appliances, wi-fi, cable, grill, about one mile walk t ...
From $726 per night (USD)
Expedia

Search Your Destination Now!

Dukes Area Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 960 Rentals