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

Filter

Popular Areas

Click For Pricing
VRBO
1 Bedroom, Sleeps 4; perfect small family vacation home
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Close to town and beach, but far enough away for peaceful quiet. 1 Bedroom; 3.5 bath; outdoor shower; front and side por ...
Click For Pricing
VRBO
From $521 per night (USD)
Expedia
Guest House In Edgartown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Relax with the whole family at this peaceful place to stay. Experience island living at this one-bedroom, one-bathroom g ...
From $521 per night (USD)
Expedia
From $597 per night (USD)
VRBO
Beautiful Chilmark beach house. Great screen porch. Fun house. Pet friendly.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Wonderful screen porch overlooking gorgeous setting. Right off South Road, a few minutes to fishing village of Menemsha ...
From $597 per night (USD)
VRBO
From $762 per night (USD)
Expedia
The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Welcome to The Field House — a beautifully designed modern home overlooking a serene island pasture, where open-concept ...
From $762 per night (USD)
Expedia
From $1984 per night (USD)
VRBO
Gorgeous South Beach Contemporary 5 min walk to beach with AC, and WiFi
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Quintessential South Beach Vineyard vacation home on 1.5 private acres. This home is a short walk to South Beach, close ...
From $1984 per night (USD)
VRBO
From $617 per night (USD)
Expedia
Edgartown cottage in a garden setting. New and near bike path in Katama
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This Edgartown cottage is close to town and the beach, newly built and furnished for summer of 2024. The cozy atmosphere ...
From $617 per night (USD)
Expedia
$Welcome to \Suzy's Place\ Best Location! Walk Everywhere. Newly built in 2024.$
From $847 per night (USD)
VRBO
Welcome to \"Suzy's Place\" Best Location! Walk Everywhere. Newly built in 2024.
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
"Suzy's Place" is arguably the best location on the island. Your cozy getaway awaits in Oak Bluffs at this beautiful new ...
From $847 per night (USD)
VRBO
From $957 per night (USD)
Expedia
Brand New Guest house
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Located in Oak Bluffs, enjoy what this 2-bedroom apartment has to offer. With a washing machine, WiFi, AC, iron, hair dr ...
From $957 per night (USD)
Expedia
From $792 per night (USD)
VRBO
Charming 2-bedroom house on Chappy with pool, Tennis, pickleball, WiFi and AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Chappaquiddick is a perfect oasis from busyness of Edgartown. The island has nature trails and gorgeous beaches. The hou ...
From $792 per night (USD)
VRBO
From $1364 per night (USD)
Expedia
Vineyard Haven Family Beach, Fire Pit & Garden View
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Summary: Escape to Vineyard Haven House, a stunning holiday home perfect for your next getaway! This beautiful house bo ...
From $1364 per night (USD)
Expedia
From $1484 per night (USD)
VRBO
Great Vineyard getaway!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Your cozy getaway awaits in Edgartown at this beautiful house. With 3 bedrooms, including 2 queen beds, 2 twin beds, and ...
From $1484 per night (USD)
VRBO
From $529 per night (USD)
Expedia
BRAND NEW 1-bedroom Owner's Suite in wonderful Oak Bluffs with Air Conditioning
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Get ready to relax in this 1-bedroom Owner's Suite in Oak Bluffs. This brand new property features a cozy bedroom with a ...
From $529 per night (USD)
Expedia
From $747 per night (USD)
VRBO
Spacious 5-bedroom secluded house in West Tisbury - Lambert Cove's Beach Pass
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Nestled on 1.55 acres off West Tisbury Road, this tranquil, 5-bed, spacious, family-friendly retreat offers established ...
From $747 per night (USD)
VRBO
Click For Pricing
Expedia
Peaceful Scenic Up-Island Retreat With Private Martha's Vineyard Beach
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Simpler, secluded living, just 5 minutes walk through woods to a gorgeous private beach, where stairs lead down from a s ...
Click For Pricing
Expedia
From $556 per night (USD)
VRBO
Spacious Second FL 4-Bedroom Rental – Private Entrance & Newly Renovated Deck!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Spacious 4-Bedroom Rental in Oak Bluffs – Private Entrance & Newly Renovated Deck! Enjoy the best of Oak Bluffs in this ...
From $556 per night (USD)
VRBO
From $894 per night (USD)
Expedia
Steps to Inkwell Beach: Victorian Home!
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
2,150 Sq Ft | Family Friendly | Walk to Shops, Restaurants, Ferry Terminal | Outdoor Shower & Grill It doesn't get any ...
From $894 per night (USD)
Expedia
From $1184 per night (USD)
VRBO
Victorian cottage overlooking downtown Oak Bluffs and the Harbor.
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Come stay at our quaint Victorian cottage overlooking downtown Oak Bluffs and the Harbor, which are just a few blocks aw ...
From $1184 per night (USD)
VRBO
From $6836 per night (USD)
Expedia
Brand New Spacious Luxury Home on Edgartown Great Pond with Pool and Spa
Bedrooms:
8
Bathrooms:
7
Sleeps:
14
STUNNING NEW 7 BEDROOM LUXURY HOME, 7 BATHS, HEATED SALTWATER POOL, MULTIPLE DECKS, SCREENED PORCH, WATERVIEW, ON THE ED ...
From $6836 per night (USD)
Expedia
From $693 per night (USD)
VRBO
4 Mi to Inkwell Beach: Home in Oak Bluffs!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
'Clark's Cove' | Idyllic Tree-Lined Surroundings | Outdoor Shower | 3 Mi to Ferry Terminal Your own slice of paradise a ...
From $693 per night (USD)
VRBO
From $713 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 $713 per night (USD)
Expedia
From $922 per night (USD)
VRBO
Welcome to your perfect island retreat nestled in a private Oak bluffs Enclave
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
This light filled modern, five ensuite bedrooms plus half bath home has everything you need for a perfect getaway. On t ...
From $922 per night (USD)
VRBO
From $891 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 $891 per night (USD)
VRBO
From $1231 per night (USD)
VRBO
Spacious 5BR Vineyard Haven Home - Walk to Town, Bike to Tashmoo - Sleeps 10!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Spacious 5-bedroom Vineyard Haven home designed for multi-family getaways and group vacations. The home is close to ever ...
From $1231 per night (USD)
VRBO
From $1015 per night (USD)
Expedia
Charming 1-bedroom bungalow with AC in Oak Bluffs
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Stay comfortably in Oak Bluffs at this newly built delightful 1-bedroom bungalow. The bedroom features a cozy queen bed, ...
From $1015 per night (USD)
Expedia
From $1658 per night (USD)
VRBO
Davis Upstairs: sunlight and garden views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Tisbury upstairs apartment boasts 3 inviting bedrooms, including a king bed and two queen beds. Guests enjoy two ba ...
From $1658 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Walk to Ferry & Beach from Central Oak Bluffs
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: 3A Circuit Breeze The Space: Welcome to Circuit Breeze, a bright and comfortable first-floor retreat desig ...
From $669 per night (USD)
Expedia
From $1216 per night (USD)
VRBO
Relax & Unwind: Poolside Martha’s Vineyard Stay
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Luxury Vineyard Haven Home w/ Pool & Game Room Vineyard Haven Luxury Retreat with Pool, Foosball & Central Location We ...
From $1216 per night (USD)
VRBO
From $955 per night (USD)
Expedia
Luxury Log Villa with Endless Pool, Hot Tub & Expansive Grounds
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Discover your private retreat on Martha’s Vineyard. Set on ¾ of an acre of beautifully landscaped, ultra-private grounds ...
From $955 per night (USD)
Expedia
From $903 per night (USD)
VRBO
Charming, artistic 3-bedroom farmhouse walk to town and ferry, doggies welcome!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Get ready to relax in this 3-bedroom farmhouse in Tisbury! The first floor master has a luxury Marriott king bed with ma ...
From $903 per night (USD)
VRBO
From $734 per night (USD)
Expedia
New 5BR Luxury Home Near Ferry – Huge Deck, Fire Pit, Sleeps 12
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Legacy House is a beautifully built 2020 colonial that has been completely redesigned for the 2026 season with all new f ...
From $734 per night (USD)
Expedia
From $430 per night (USD)
VRBO
Oak Bluffs home conveniently located.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Plan your escape to Martha's Vineyard! Conveniently located near downtown Oak Bluffs, this 2BD/2BA home provides easy ac ...
From $430 per night (USD)
VRBO
From $5393 per night (USD)
Expedia
The Ultimate Group Escape on Marthas Vineyard
Bedrooms:
3
Bathrooms:
6
Sleeps:
18
Summary: Circuit Breeze, Sand By Me & Whale Tail Retreat The Space: Experience the ultimate Martha’s Vineyard getaw ...
From $5393 per night (USD)
Expedia
From $528 per night (USD)
VRBO
lovely Lambert's Cove home, walking to beach and two swimming ponds.
Bedrooms:
1
Bathrooms:
4
Sleeps:
11
Discover the stunning beauty of Lambert's Cove beach and surround spring-fed ponds in our warm and comfortable home, wit ...
From $528 per night (USD)
VRBO
From $1181 per night (USD)
Expedia
Family Friendly Hidden Oaks Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Located a short stroll away from Oak Bluffs harbor (and a 10-minute drive to the town beach), this serene home is centra ...
From $1181 per night (USD)
Expedia
From $1042 per night (USD)
VRBO
Spacious island home near Farm Neck Golf Course, the beach and town
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Twin Ponds The Space: Nestled just a stone's throw away from the renowned Farm Neck golf course in Oak Blu ...
From $1042 per night (USD)
VRBO
From $1281 per night (USD)
Expedia
Inviting home near town and the beach with fast WiFi and private W/D
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Island Oasis The Space: Find yourself living the island lifestyle in no time when you book a stay at this ...
From $1281 per night (USD)
Expedia
From $502 per night (USD)
VRBO
Quaint, ranch style home in Oak Bluffs with central air
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Summary: The Rootskeller The Space: Nestled at the end of a tranquil cul de sac, this charming cabin-style home in ...
From $502 per night (USD)
VRBO
From $706 per night (USD)
Expedia
Charming home set on private lot with WiFi, sunroom, W/D, & great location
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
Summary: Pretty on Prada The Space: Charming and quaint, this four-bedroom cedar shake home set on a private, woode ...
From $706 per night (USD)
Expedia
From $586 per night (USD)
VRBO
Family friendly, walking distance to town, harbor, shops, restaurants, beaches
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Summary: Canary Cottage The Space: Experience the Martha's Vineyard of yesteryear at this beautifully updated histo ...
From $586 per night (USD)
VRBO
From $731 per night (USD)
Expedia
Nana’s Treehouse | House with spacious deck, grills, outdoor shower & W/D
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Summary: Nana’s Big Treehouse The Space: Escape from the hustle and bustle of daily city life and reconnect with na ...
From $731 per night (USD)
Expedia
From $705 per night (USD)
VRBO
Inviting, two-story home with a large yard, sunroom, balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Gingerbread Dream The Space: Experience the laidback lifestyle of the Vineyard from this classic, two-stor ...
From $705 per night (USD)
VRBO
From $810 per night (USD)
Expedia
Historical house with wraparound porch, modern updates, enclosed yard, & W/D
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Summary: Victorian by the Sea The Space: A unique coastal stay awaits you and yours at this newly renovated, grand ...
From $810 per night (USD)
Expedia
From $1087 per night (USD)
VRBO
Spacious home in central location with beautiful patio, pool table, W/D, & AC
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: Bird Street Breeze The Space: Nestled in a quiet neighborhood next door to the public library (with access ...
From $1087 per night (USD)
VRBO
From $3152 per night (USD)
Expedia
2-story home near Crystal Lake with partial views, deck, grill, outdoor shower
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Summary: Vineyard State of Mind The Space: Centrally located within one and a half miles of downtown Oak Bluffs, th ...
From $3152 per night (USD)
Expedia
From $724 per night (USD)
VRBO
Updated house close to town and beach with patio, AC, and games
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Summary: Sankofa House The Space: Nestled in the historic Vineyard Highlands at the beginning of the African Americ ...
From $724 per night (USD)
VRBO
From $355 per night (USD)
Expedia
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Lemonade Stand The Space: Located just down the street from Long Point Wildlife Refuge, this quaint ho ...
From $355 per night (USD)
Expedia
From $1069 per night (USD)
VRBO
Private island house with close beach access and water view from deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Summary: Soundmeadow House The Space: Located just outside the charming town of Oak Bluffs, MA, this delightful hou ...
From $1069 per night (USD)
VRBO
From $680 per night (USD)
Expedia
Gorgeous home near the ocean w/ a full kitchen, deck, & large, fenced back yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Grimmett Retreat The Space: Come experience paradise at Martha's Vineyard at this spacious, rustic home. Y ...
From $680 per night (USD)
Expedia
From $1027 per night (USD)
VRBO
House with guest studio close to town and beach with grill, games, AC & patio
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: Sankofa Martha's Vineyard The Space: Nestled in the historic Vineyard Highlands at the beginning of the Af ...
From $1027 per night (USD)
VRBO
From $727 per night (USD)
Expedia
Charming Martha's Vineyard retreat close to beaches & downtown - large yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Set Sail The Space: Set, sail, and settle down at this charming Martha's Vineyard hideaway! Showcasing one ...
From $727 per night (USD)
Expedia
From $1340 per night (USD)
VRBO
Charming home with private hot tub, firepit, deck, grill, outdoor shower, AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Tiffany's Treasure The Space: This two-story home will be just the perfect place to bring the whole family ...
From $1340 per night (USD)
VRBO
From $1200 per night (USD)
Expedia
Charming home near downtown & beach with patio, outdoor shower, grill, & W/D
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Blissful Island Haven The Space: Centrally located within a half-mile of Inkwell Beach and a mile of downt ...
From $1200 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Cottage w/ water views from front yard, central ac & fireplace
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Island Home The Space: Steps from the beach and walking distance to town, this adorable cottage cottage is ...
From $570 per night (USD)
VRBO
From $311 per night (USD)
Expedia
Stylish island retreat with sunny interiors, wraparound deck, firepit & AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Fresh Pond Chateau The Space: Welcome to Fresh Pond Chateau, a beautifully renovated cottage nestled on a ...
From $311 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Central 2nd-floor apartment with propane stove, grill, W/D, & great location
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Summary: Main Street Upper The Space: Tisbury Town Beach, Owen Park Beach, and Vineyard Haven shops, restaurants, a ...
From $447 per night (USD)
VRBO
From $838 per night (USD)
Expedia
Spacious colonial home close to town with AC, porches, & W/D
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Seabreeze Retreat The Space: Welcome to your perfect summer retreat in Oak Bluffs, MA! This charming house ...
From $838 per night (USD)
Expedia
From $537 per night (USD)
VRBO
Walk-up apartment with deck & grill - walk to beach & town
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Everyday is Saturday The Space: Find yourself within easy reach of the best Martha's Vineyard offers with ...
From $537 per night (USD)
VRBO
From $1102 per night (USD)
Expedia
Historic, dog-friendly beach view house with fast WiFi, ocean view, & grill
Bedrooms:
4
Bathrooms:
6
Sleeps:
11
Summary: Captain Shaw Norris House The Space: Don't miss your chance to book this incredible historic beach view ho ...
From $1102 per night (USD)
Expedia
From $565 per night (USD)
VRBO
Charming 2-story house near the beach with inviting deck, large yard & canoe
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Summary: Nana’s Treehouse The Space: Take some time to relax and reconnect with nature at this beautifully furnishe ...
From $565 per night (USD)
VRBO
From $1000 per night (USD)
Expedia
Enchanting home with tennis, firepit, golf nearby & washer/dryer
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Summary: Bird's Paradise The Space: Find serenity on the coastal bay of Martha's Vineyard with this fantastic getaw ...
From $1000 per night (USD)
Expedia
From $681 per night (USD)
VRBO
Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Sunset Meadows The Space: The stunning waterways and marshlands of Martha's Vineyard are just outside your ...
From $681 per night (USD)
VRBO
From $700 per night (USD)
Expedia
Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Fallen Oak Retreat The Space: Located in the historic Oak Bluffs neighborhood, this recently remodeled 3BR ...
From $700 per night (USD)
Expedia
From $468 per night (USD)
VRBO
Bright old-world cottage with two porches & large yard - walk to town & beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Oak Bluffs Cottage The Space: Savor the old-world charms of Oak Bluffs Cottage, an ideally situated Martha ...
From $468 per night (USD)
VRBO
From $920 per night (USD)
Expedia
Charming Home with Deck, Screened Porch, Private Balcony, Near Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Katama Woods The Space: This lovely 3BR/2BA home provides abundant opportunities for outdoor enjoyment. Gr ...
From $920 per night (USD)
Expedia
From $783 per night (USD)
VRBO
Cozy island cottage near local attractions with breezy yard & inviting interior
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: TumbleINN The Space: Welcome to your ideal island retreat in Oak Bluffs, where unforgettable family vacati ...
From $783 per night (USD)
VRBO
From $1584 per night (USD)
Expedia
Private house with jetted tub, deck, grill, central AC and large yard
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Family Getaway The Space: Welcome to your perfect getaway in Oak Bluffs, MA! This charming house offers a ...
From $1584 per night (USD)
Expedia
From $1060 per night (USD)
VRBO
Historic cottage with patio, games, walk to beach & dog-friendly fenced yard
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Summary: Pilgrim Cottage The Space: Welcome to Pilgrim Cottage, your cozy home base for an authentic Martha’s Viney ...
From $1060 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: Nana's Backyard Treehouse The Space: Take some time to relax and reconnect with nature at this splendid sm ...
From $336 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Coastal home with outdoor shower, grill, fireplace, central AC, & W/D
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Yellow Brick Road House The Space: Bright and inviting, this home provides an ideal escape for your family ...
From $389 per night (USD)
VRBO
From $827 per night (USD)
Expedia
4 bedroom cottage in Oak Bluffs Martha's Vineyard
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Nestled in Oak Bluffs, this delightful cottage offers 4 bedrooms - 3 with queen beds, one with 2 twin beds, With 2 bathr ...
From $827 per night (USD)
Expedia
From $891 per night (USD)
VRBO
Wayland Victorian in Oak Bluffs
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Wayland Victorian in Oak Bluffs Victorian Charm in Oak Bluffs – Walk to Beaches & Harbor Enjoy one of the best spots o ...
From $891 per night (USD)
VRBO
From $1417 per night (USD)
Expedia
Marvelous 4-bedroom townhome with AC in charming Edgartown
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Consider this townhome your home away from home while you visit Edgartown. This fabulous space features four bedrooms, i ...
From $1417 per night (USD)
Expedia
From $1005 per night (USD)
VRBO
Beach, Shop, Restaurants, Bike Path: 4 Min. to Town! Bikes & Beach Gear Included
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Your Edgartown retreat begins at this beautiful 3-bedroom, 2 full bath house. One of the biggest advantages of this home ...
From $1005 per night (USD)
VRBO
From $1106 per night (USD)
Expedia
A Love Letter to Martha's Vineyard New Build, Luxe Design
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Fleetwood Farm — a modern barn set into ancient farmland, down a quiet lane and surrounded by a permanently p ...
From $1106 per night (USD)
Expedia
From $1450 per night (USD)
VRBO
Sunny & Spacious luxury 4-bedroom Katama beach house. Walk to South Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Coastal Luxury & Vineyard Charm – Walk to the Beach in Edgartown Listen to the sounds of the surf as you relax on one o ...
From $1450 per night (USD)
VRBO
From $597 per night (USD)
Expedia
2 Mi to Main St & Beach! Family Home in Edgartown
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Outdoor Shower | Day Trip to Boston From beach days to unforgettable sunsets, this breezy Edgartown vacation rental off ...
From $597 per night (USD)
Expedia
From $785 per night (USD)
VRBO
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**guests must provide: Bedsheets, pillowcases, bath towels, hand towels and beach towels. Washer and Dryer are located i ...
From $785 per night (USD)
VRBO
From $1340 per night (USD)
Expedia
Historic Oak Bluffs Cottage – Porch with View
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Historic Oak Bluffs Cottage – Porch with View Step into the charm of a bygone era at this classic Oak Bluffs home, fill ...
From $1340 per night (USD)
Expedia
From $657 per night (USD)
VRBO
Edgartown Escape – Walk to Beach & Downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Edgartown Escape – Walk to Beach & Downtown Spacious Edgartown Retreat – Walk to Beach & Downtown Discover the charm o ...
From $657 per night (USD)
VRBO
From $1223 per night (USD)
Expedia
Charming Vineyard Haven Retreat w/ Heated Pool, Walk to Town, & Tashmoo Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to a private Vineyard Haven retreat where sun-soaked pool days meet effortless access to town and beaches. Design ...
From $1223 per night (USD)
Expedia
From $628 per night (USD)
VRBO
Family Home Near Arts District & Inkwell Beach
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Family Home Near Arts District & Inkwell Beach Family-Friendly Home with Backyard – 1 Mile to Beach Bring the whole fa ...
From $628 per night (USD)
VRBO
From $2690 per night (USD)
Expedia
4-bedroom house with AC and heated saltwater pool walking distance to Edgartown
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Relax by the heated 8 x 19’ pool or stroll to the shops and restaurants of Edgartown without the hassle of finding park ...
From $2690 per night (USD)
Expedia
From $1049 per night (USD)
VRBO
Dog-friendly home with beautiful deck & AC - close to 3 towns & great beaches
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Martha's Hideaway The Space: Charming towns, beautiful beaches, and renowned golf courses are yours to exp ...
From $1049 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Chilmark Guest House The Space: Tucked away in a private glen on three secluded acres, this light-filled h ...
From $398 per night (USD)
Expedia
From $478 per night (USD)
VRBO
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Winthrop Cottage The Space: If you are planning a family vacation to Martha's Vineyard, consider this affo ...
From $478 per night (USD)
VRBO
From $1028 per night (USD)
Expedia
Newly remodeled home w/ new furniture, large yard & great porches
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Sunny Side Up The Space: Freshly remodeled with brand new furnishings throughout, this Oak Bluffs home is ...
From $1028 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Quaint home across from bike paths with large furnished deck, grill, & W/D
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: The C-Haven The Space: Escape to the charming town of West Tisbury and stay at the delightful C-Haven hous ...
From $391 per night (USD)
VRBO
From $358 per night (USD)
Expedia
Cozy getaway in a central location w/ a full kitchen & furnished deck
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Sea Glen Cottage The Space: This lovely cottage awaits you for your next Martha's Vineyard getaway with th ...
From $358 per night (USD)
Expedia
From $616 per night (USD)
VRBO
New Construction with Patio & Yard - Downtown & Beaches
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Oak Bluffs Beauty The Space: Immerse yourself in the charms of Oak Bluffs at this Martha's Vineyard home, ...
From $616 per night (USD)
VRBO
From $1070 per night (USD)
Expedia
Elegant Dream Home w/ Luxurious Living Spaces, Full Kitchen, & Wraparound Porch
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Oak Manor The Space: Welcome to your dream getaway in the charming town of Oak Bluffs, MA! This delightful ...
From $1070 per night (USD)
Expedia
From $1880 per night (USD)
VRBO
Charming home with walkable beach, large yard, deck, fire pit, and A/C
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Summary: Beach House The Space: Nestled in a tranquil neighborhood of Oak Bluffs, this charming and spacious home o ...
From $1880 per night (USD)
VRBO
From $661 per night (USD)
Expedia
Welcoming island cottage with patio & enclosed yard - close to town & beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Cozy Corner The Space: Escape to Martha's Vineyard and book your next stay at this adorable cottage in Edg ...
From $661 per night (USD)
Expedia
From $611 per night (USD)
VRBO
Private suite with roof deck, near golf, bus stop, shops, and trails
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Garage Suite The Space: Welcome to our cozy one-bedroom suite, a perfect retreat for couples or solo trave ...
From $611 per night (USD)
VRBO
From $1517 per night (USD)
Expedia
Bright spacious downtown home; walk to beach & lighthouse
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Edgartown Village The Space: Welcome to your idyllic retreat in the heart of Edgartown, MA, where relaxati ...
From $1517 per night (USD)
Expedia
From $1046 per night (USD)
VRBO
Serene private home w/ large deck & yard on conservation land
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Summary: The Big Easy The Space: Welcome to your perfect family getaway in Oak Bluffs, MA! Nestled on a serene cul- ...
From $1046 per night (USD)
VRBO
From $522 per night (USD)
Expedia
Great Ranch Style Home In Edgartown W/ Gas Grill & Dog Friendly
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: Old Orchard The Space: Get away to the summer colony of Martha’s Vineyard and change your pace to island t ...
From $522 per night (USD)
Expedia
From $465 per night (USD)
VRBO
Cozy in-law suite near Edgartown & the beach with patio, outdoor shower, & AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Little Cozy Corner The Space: This adorable one-bedroom cottage in Edgartown awaits your next Martha's Vin ...
From $465 per night (USD)
VRBO
From $620 per night (USD)
Expedia
Beautiful Estate with Large Lawn Made for Socializing and Kids' Playroom
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Summary: The CAVU Mansion on Bellevue The Space: With a spacious interior ranging from formal to casual, a separate ...
From $620 per night (USD)
Expedia
From $1856 per night (USD)
VRBO
Quaint home w/ large backyard, outdoor shower & private grill near Katama Bay
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Need a Bigger Boat The Space: This Edgartown property is a beautiful blend of island living and wooded pri ...
From $1856 per night (USD)
VRBO
From $1268 per night (USD)
Expedia
Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Hillside Oak The Space: Nestled in the serene scrub oak forest of Chilmark, this stunning 4-bedroom home o ...
From $1268 per night (USD)
Expedia

Search Your Destination Now!

Dukes Area Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 861 Rentals