Dukes Area Rentals
From $1857 per night (USD)VRBO
Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Sunrises, sunsets and all-day sunlight grace this welcoming, elegant and beautifully-kept hilltop home. Its glorious wr ...
From $1857 per night (USD)VRBO
From $516 per night (USD)VRBO
Beautiful Contemporary Farmhouse close to Oak Bluffs
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautifully maintained contemporary farmhouse features an open floor plan. The first floor has an open kitchen, dining, ...
From $516 per night (USD)VRBO
From $1039 per night (USD)VRBO
Big Beach House - Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Original 1900 Victorian home, updated in 2006, located in the historic Copeland District just one block from the beach. ...
From $1039 per night (USD)VRBO
From $301 per night (USD)Expedia
Chappaquiddick, Cozy 2 Bedroom, October Dates Available!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
CHAPPY BUTTERFLY COTTAGE is a cozy non-posh two bedroom guesthouse with an additional sleeper sofa on the private Meadow ...
From $301 per night (USD)Expedia
From $261 per night (USD)VRBO
Contemporary Pet-friendly Retreat. Just one 2025 summer week left: Aug 30-Sep 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Contemporary with open living/dining area, cathedral ceilings, and air conditioning throughout. Sliding and French door ...
From $261 per night (USD)VRBO
From $658 per night (USD)VRBO
Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Superb fields-to-ocean-to-islands views from this charming guesthouse, on a historic Chilmark property. You'll enjoy a ...
From $658 per night (USD)VRBO
From $424 per night (USD)VRBO
Martha's Vineyard Beachfront Condo in Oak Bluffs
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy all that Martha's Vineyard has to offer in this spacious two bedroom, two full bath beautifully furnished condo ov ...
From $424 per night (USD)VRBO
From $566 per night (USD)VRBO
Classic Downtown Property
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The home has been tailored for modern tastes and conveniences. Ideally located on a private lane, just a short distance ...
From $566 per night (USD)VRBO
From $1285 per night (USD)VRBO
Private home, spacious yard. Easy access to downtown Edgartown and beaches.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Recently renovated and stocked with everything you need for a fun and relaxing island getaway, this 4BR, 3.5Bth is locat ...
From $1285 per night (USD)VRBO
From $659 per night (USD)VRBO
Edgartown Long Point Escape, Very Spacious Quite Private Location, Central A/C
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
House Beautiful. Custom Home. CENTRAL AIR CONDITIONING for your comfort. This spacious, over sized luxury L-shaped Cape ...
From $659 per night (USD)VRBO
From $1077 per night (USD)VRBO
Secluded Escape- Central AC & Wireless Internet Access.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 270 ...
From $1077 per night (USD)VRBO
From $226 per night (USD)VRBO
Sea Captain's Victorian studio bedroom apartment. Pets OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay in an original sea captain Victorian for less than the cost of a hotel. This is a fully furnished studio apartment ...
From $226 per night (USD)VRBO
From $989 per night (USD)VRBO
Lovely waterfront home with private, sandy beach and mooring on Lagoon Pond
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax on the gorgeous wraparound deck, let the sea breeze caress your face, listen to the chirping birds, and drink in t ...
From $989 per night (USD)VRBO
From $637 per night (USD)Expedia
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Prime location close to the center of town in the fabulous SeaView Condo building in the heart of Oak Bluffs. Highly des ...
From $637 per night (USD)Expedia
From $446 per night (USD)VRBO
Martha's Vineyard House - Great Rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our colonial style is located in the desirable Katama area of Edgartown, two miles from the beach and downtown. It offer ...
From $446 per night (USD)VRBO
From $333 per night (USD)Expedia
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a peaceful retreat in this cozy 2-bedroom, 2-bath condo with air conditioning, offering the perfect space to relax ...
From $333 per night (USD)Expedia
From $937 per night (USD)VRBO
Charming1700's Edgartown Village Cottage 5 Minute walk to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Charming & Historical Circa 1700 Edgartown Village Classic with original pumpkin pine floors throughout. Fuller Street b ...
From $937 per night (USD)VRBO
From $489 per night (USD)VRBO
Fabulous Makonikey with multi-levels & multi-decks ~WALK TO PRIVATE BEACH! A/C!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 10
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you w ...
From $489 per night (USD)VRBO
From $730 per night (USD)VRBO
'Seaglass Cottage' in Katama, near Edgartown and South Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
''Unique and charming'' island artist's home with endless amenities and extras. This is not your average rental propert ...
From $730 per night (USD)VRBO
From $1840 per night (USD)VRBO
Glorious Sunsets and Fun on Private Waterfront in Beautiful, Comfortable Home.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Ask about Discounts if 8 or fewer guests. ...
From $1840 per night (USD)VRBO
From $1543 per night (USD)VRBO
7/6-7/13 AVAILABLE DUE TO LAST MINUTE CANCELLATION! Walk to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
LAST MINUTE CANCELLATION FOR JULY 6TH - 13TH, 2025!! This charming Vineyard home just completed a large renovation incl ...
From $1543 per night (USD)VRBO
From $1360 per night (USD)VRBO
Glorious Water View, private beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This spectacular beach house with stunning water views is located 20 feet from the edge of a grassy cliff overlooking Vi ...
From $1360 per night (USD)VRBO
From $614 per night (USD)VRBO
A Charming Vineyard Cottage Just Off the Pond
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Remember when summer vacations meant spending long perfect days near the water? This simple wooden Vineyard cottage wit ...
From $614 per night (USD)VRBO
From $564 per night (USD)VRBO
Open July 20-27th w/RT Ferry! 4 BR Cape in Chilmark - Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A recently renovated country home located in the Vineyard's most idyllic town of Chilmark, close to the West Tisbury lin ...
From $564 per night (USD)VRBO
From $809 per night (USD)VRBO
The quintessential MV home. Now booking for 2026!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Pirate's Cove is a young, Victorian-style home, designer-decorated and nestled on a quiet lane in East Chop, located jus ...
From $809 per night (USD)VRBO
From $335 per night (USD)VRBO
Beautiful Landscaped Grounds and Pond & Kayaks
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to paradise!!! This beautiful property is located in prestigious fresh pond estates. It sits tucked away in the ...
From $335 per night (USD)VRBO
From $222 per night (USD)VRBO
Central location for your vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Centrally located from nearby Vineyard Haven, Oak Bluffs, Edgartown and West Tisbury. Beaches and trails in close proxi ...
From $222 per night (USD)VRBO
From $455 per night (USD)VRBO
WALK TO BEACHES,HARBOR,EVERYTHING!! IN-TOWN OB! A/C,Large Deck,Gazebo,Yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you ...
From $455 per night (USD)VRBO
From $2294 per night (USD)VRBO
Private Katama Beach House. Repeat Guests Love It. Limited Avail Summer/Fall '26
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
See the ocean, hear the ocean, and smell the ocean from our light-filled contemporary home. The design is perfect for a ...
From $2294 per night (USD)VRBO
From $612 per night (USD)VRBO
Hamletts' Haven - Spectacular Summer Getaway! Tues. 8/27 - Sat. 9/7 AVAILABLE!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Hamletts' Haven - The Vacation Get Away! Book for two days or two weeks - the choice is yours. Enjoy!!!! ...
From $612 per night (USD)VRBO
From $796 per night (USD)VRBO
FAMILY VACATION- JULY14-21-SLEEP 10, PVT, LONG POINT BEACH
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Certificate #/ Ma. tax: C0221072960 Wonderful, spacious, light and airy home which sits on a private 2 acre prop ...
From $796 per night (USD)VRBO
From $829 per night (USD)VRBO
FABULOUS Makonikey OCEANFRONT With Private Beach !Wrap Around Deck, Pets Ok, A/C
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you w ...
From $829 per night (USD)VRBO
From $834 per night (USD)VRBO
Great Martha's Vineyard House: Everything You Need - Nothing You Don't!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 9
Property rents Monday to Monday. 3 bedroom/ 2 and 1/2 bathroom Contemporary Vineyard house with wraparound deck, outdoor ...
From $834 per night (USD)VRBO
From $258 per night (USD)VRBO
Carriage House, Swimming, Boating, Kayaking, just steps from your door...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
WELCOME TO PARADISE!!! we sanitize!!!!! We have implemented a system so you are able to check in and out without and per ...
From $258 per night (USD)VRBO
From $838 per night (USD)VRBO
Aquinnah Beachfront, Perfect Sunsets, Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
*NOTE* We Just opened the calendar for the month of August! These weeks will go quickly. This is a very rare opportunity ...
From $838 per night (USD)VRBO
From $809 per night (USD)VRBO
Beautiful Katama House between Edgartown and South Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax and enjoy this beautifully renovated, immaculate Katama home centrally located 1 1/2 miles to South Beach and down ...
From $809 per night (USD)VRBO
From $1165 per night (USD)VRBO
Classic, upscale Chilmark farmhouse and PRIVATE BEACH KEY
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
One of Chilmark's most stately and classic Captains House, THE BLUE BARQUE has been thoughtfully and fashionably edited ...
From $1165 per night (USD)VRBO
From $598 per night (USD)VRBO
Katama Beautifully Landscaped close to Beach/Edgartown - Air conditioned
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
When you check in you will find our home super cleaned by a professional cleaning service. During the summer we normal ...
From $598 per night (USD)VRBO
From $801 per night (USD)VRBO
Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches!
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 10
Victorian Cape Cod Cottage located in the highly desired Oak Bluffs Copeland District in Martha's Vineyard. Large family ...
From $801 per night (USD)VRBO
From $493 per night (USD)Expedia
West Tisbury Country Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Custom home with many amenities. Nicely furnished. Beautiful interiors with natural woodwork, oak floors, deck, big secl ...
From $493 per night (USD)Expedia
From $1469 per night (USD)VRBO
Katama House w/Guest House w/AC South Beach heated pool. \nSummer weeks avail. \n
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Katama Beach House with guest cottage large enough for 2 families. INGROUND HEATED POOL. Terrific Wrap Around Deck and S ...
From $1469 per night (USD)VRBO
From $1559 per night (USD)VRBO
Luxe 4 Bed/4 Ensuite Bath, A/C In-Town Vineyard Haven, Gunite Pool and Spa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Luxury Home in private cul-de-sac in Vineyard Haven. Just a short two block walk to downtown restaurants, shops, harbor, ...
From $1559 per night (USD)VRBO
From $754 per night (USD)VRBO
Ocean & Harbor Views, Chappy Privacy yet Walk to Town or Private Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Contemporary Cape high on Chappy's Manaca Hill with views to Cape Cod (north), Edgartown Harbor (south). Major expansio ...
From $754 per night (USD)VRBO
From $1242 per night (USD)VRBO
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A unique opportunity to spend your vacation in peaceful Abel’s Hill in Chilmark. This lovely cottage is located in the h ...
From $1242 per night (USD)VRBO
From $1483 per night (USD)VRBO
Modern & Spacious Edgartown Home with Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy your vacation in this wonderfully charming three bedroom home with an in-ground heated pool. Head to the beach or ...
From $1483 per night (USD)VRBO
From $758 per night (USD)Expedia
Dog-friendly home with beautiful deck & AC - close to 3 towns & great beaches
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Martha's Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $758 per night (USD)Expedia
From $526 per night (USD)VRBO
Renovated 4 bedroom home in Vineyard Haven
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Renovated contemporary 4-bedroom/3-bath home is tastefully furnished and equipped with new appliances and all the amenit ...
From $526 per night (USD)VRBO
From $1057 per night (USD)VRBO
Luminous rural retreat with spectacular ocean views.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Tucked into the woods, this elegant house offers a panoramic view of the full sweep of the Vineyard Sound from Woods Ho ...
From $1057 per night (USD)VRBO
From $942 per night (USD)VRBO
Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!!\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Think resort-type elegance in a relaxed beach house vibe. 4BR, 3 bath, outdoor shower, 4-ft deep spa pool. Lots of light ...
From $942 per night (USD)VRBO
From $405 per night (USD)VRBO
Charming Oak Bluffs Cottage: Prime Location, Stylish Comfort & Serene Privacy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your Vineyard getaway! Nestled in a peaceful neighborhood in Oak Bluffs, this cozy two-bedroom, one-bath cott ...
From $405 per night (USD)VRBO
From $588 per night (USD)VRBO
Historic Home in East Chop
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Renovated home in East Chop, Oak Bluffs, Martha’s Vineyard. Built in 1872 by my great, great grandfather, the house has ...
From $588 per night (USD)VRBO
From $383 per night (USD)VRBO
Updated Beautiful Cottage in Edgartown w/ Central AC
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
A true island charmer. Light, airy and central-air-conditioned, well-designed home offers all the comforts of modern liv ...
From $383 per night (USD)VRBO
From $1091 per night (USD)VRBO
4Br 3+Baths MV/KatamaEdgartownFamilyDelight & 7 ductless A/C airhandlers
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 13
Recent 2024 updates include replacing all remaining wall-to-wall carpeting with wooden floors in all bedrooms & upstairs ...
From $1091 per night (USD)VRBO
From $442 per night (USD)VRBO
Walk to Edgartown ctr, Bike to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We’ve blocked off October and November to enhance the property and address valuable guest feedback, focusing on comfort ...
From $442 per night (USD)VRBO
From $572 per night (USD)VRBO
Oak Bluffs Retreat - The perfect getaway!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Six minute drive to beach! This two floor beauty with central AC boasts ample yard space and all the amenities you look ...
From $572 per night (USD)VRBO
From $1296 per night (USD)Expedia
MV Beach Escape - Spacious Katama Beach House. \nBooking for 2026
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy the Katama lifestyle and summer breezes in this Wonderful 4 BR/4-BA family home on a quiet side street. Walk to S ...
From $1296 per night (USD)Expedia
From $1266 per night (USD)VRBO
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Pirate's Reef is a NEW and beautifully decorated residence that offers 5 spacious bedrooms (2 master suites!) with 4.5 b ...
From $1266 per night (USD)VRBO
From $447 per night (USD)VRBO
Charming and cozy Chappy cottage -- best of indoor and outdoor beach living!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Chappaquiddick Island -- Martha's Vineyard: Amazing single level cottage, lovingly renovated and tastefully decorated t ...
From $447 per night (USD)VRBO
From $1873 per night (USD)VRBO
Historic Captains House - Newly Renovated Primary Bathroom and Upgraded Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful restored 130 year old Sea Captain's House on historic Music Street in the heart of West Tisbury. The home was ...
From $1873 per night (USD)VRBO
From $1919 per night (USD)VRBO
Welcome to The “SUMMER WIND” House! 5-Minutes to the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
THE “SUMMER WIND” HOUSE - WALK TO EVERYTHING! We have completely renovated our 5-bedroom, 3-full bathroom home with cent ...
From $1919 per night (USD)VRBO
From $361 per night (USD)VRBO
In-Town-WALK TO EVERYTHING! PETS WELCOME! Screened Porch, A/C, Outdoor Shower
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you w ...
From $361 per night (USD)VRBO
From $590 per night (USD)VRBO
Lovely vacation home within walking distance to Oak Bluffs and the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your summer vacation home! This is a 3 bedroom 2 1/2 bath home located less than a mile from downtown Oak Bl ...
From $590 per night (USD)VRBO
From $431 per night (USD)VRBO
Edgartown House
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This charming Cape house is located at the end of private way in the desirable Katama area. Just two miles from South B ...
From $431 per night (USD)VRBO
From $604 per night (USD)VRBO
Edgartown Cottage, Short walk to town, AC/Heat, Fire Pit, Outdoor shower
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sneak in through the back kitchen door of this, simple yet luxurious, light filled cottage. Soup to nuts, almost everyth ...
From $604 per night (USD)VRBO
From $1118 per night (USD)VRBO
Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Newly renovated luxury home with 2 king sized en suites and heated pool & hot tub is centrally located! 1.5 miles to dow ...
From $1118 per night (USD)VRBO
From $3272 per night (USD)Expedia
WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
One of the best locations in Edgartown! Brand new, walk to village location but private, with mature trees and new prof ...
From $3272 per night (USD)Expedia
From $341 per night (USD)VRBO
West Tisbury Home, Peaceful, Affordable, 3 BR, Near Bike Path
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
We have an updated bathroom, newer flooring, updated bedding, freshly painted, new dining table and chairs, new kitchen ...
From $341 per night (USD)VRBO
From $408 per night (USD)VRBO
Peaceful, rural Martha's Vineyard on the Bike Path
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
If you are a bike or nature enthusiast you will love this rustic cape. It is 10 mins from the Vineyard Haven ferry and n ...
From $408 per night (USD)VRBO
From $2052 per night (USD)VRBO
Edgartown Luxury 6 BR\nHeated Pool Hot Tub!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Relax with family and friends at this fully renovated pristine 1850’s Sea Captain’s home. Situated on a quiet tree lined ...
From $2052 per night (USD)VRBO
From $572 per night (USD)Expedia
Oak Bluffs - Quiet neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Less than a mile from downtown, harbor and beach. Located in a quiet neighborhood, guests are sure to enjoy a memorable ...
From $572 per night (USD)Expedia
From $744 per night (USD)VRBO
Elegant Dream Home w/ Luxurious Living Spaces, Full Kitchen, & Wraparound Porch
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Oak Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $744 per night (USD)VRBO
From $794 per night (USD)VRBO
Spacious, Serene 3-BR, Chef's Kitchen, Meadow Views, Central Location
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
We built our beautiful family summer home in 1984 and did a full renovation in 2007, making it a wonderfully comfortable ...
From $794 per night (USD)VRBO
From $311 per night (USD)VRBO
Woods Hole Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Kitchen, living room, 3/4 bathroom with shower, washer/dryer, and outdoor shower for after the beach. 1 bedroom with que ...
From $311 per night (USD)VRBO
From $775 per night (USD)VRBO
As featured in Vineyard Style
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
As featured in the Summer 2023 issue of Vineyard Style Magazine, this house is ideally located in the highlands area of ...
From $775 per night (USD)VRBO
From $3275 per night (USD)VRBO
Maison Calme/Peaceful Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This luxury enclave, complete with 4 bedrooms and 3.5 bathrooms, is located in a private community that is centrally loc ...
From $3275 per night (USD)VRBO
From $725 per night (USD)VRBO
Private Chappaquiddick Retreat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Contemporary four-bedroom retreat with spacious layout and light-filled open living spaces and direct access to expansiv ...
From $725 per night (USD)VRBO
From $586 per night (USD)VRBO
A BRILLANT WAY\nCentral Location To Beach/Shops/Restaurants/Arcade/Family Bowling
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A Brillant Way is a Brilliant Condo located in the heart of Oak Bluffs. Second level has 2 bedrooms - Queen size bed in ...
From $586 per night (USD)VRBO
From $493 per night (USD)Expedia
Central Woods Hole Village Waterfront: Sep and Oct At 20% Off!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
**Pets and events are prohibited with no exceptions.** Commonwealth of Massachusetts recommended COVID-19 protocols no ...
From $493 per night (USD)Expedia
From $461 per night (USD)VRBO
Oak Bluffs Cutie Near Beach + Town Center! Ferry tix available for some dates!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy both worlds - a peaceful atmosphere with many comfortable places to escape to read, nap or chat, near the heart of ...
From $461 per night (USD)VRBO
From $439 per night (USD)VRBO
Edgartown - Vacation Home In A Great Location!!!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Beautiful 3 BR, 2.5 bath plus outdoor shower home on a private dead-end street in a quiet residential area, sleeps 11. C ...
From $439 per night (USD)VRBO
From $643 per night (USD)VRBO
Oak Bluffs Gingerbread Cottage near Downtown, Beach, Ferry and Ocean Park!
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 8
- Magnificent front porch for rocking and peaceful island observations! - All furniture is whimsical and light to match ...
From $643 per night (USD)VRBO
From $903 per night (USD)Expedia
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This newly renovated 2 bedroom house is a stone's throw from the ferry terminal, main street, restaurants & beaches in V ...
From $903 per night (USD)Expedia
From $1799 per night (USD)VRBO
Mink Meadows Luxury Getaway With Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
POINT B EXCLUSIVE - This luxuriously renovated home is privately set in the Mink Meadows neighborhood with access to a p ...
From $1799 per night (USD)VRBO
From $395 per night (USD)VRBO
Martha’s Vineyard Condo w/ Pool minutes from Ferry
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cozy 1 bedroom, 1 full bath, Condo located minutes from Vineyard Haven Harbor on Martha’s Vineyard. Nice landscaped surr ...
From $395 per night (USD)VRBO
From $745 per night (USD)VRBO
Spacious Beach house.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Windows and French doors abound in this impeccable air-conditioned 4400 plus square foot contemporary. Located 1.2 m ...
From $745 per night (USD)VRBO
From $306 per night (USD)Expedia
Secluded West Tisbury Retreat. Surrounded by Acres of Conservation Trails.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Haven. Escape to a one-of-a-kind cottage in the woodlands of West Tisbury. Romantic. Inspiring. Secluded. Serene. ...
From $306 per night (USD)Expedia
From $653 per night (USD)VRBO
Secluded Waterfront - North Shore - Private Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Charming waterfront cottage on the North Shore of Aquinnah overlooking the Elizabeth Islands with panoramic water views. ...
From $653 per night (USD)VRBO
From $499 per night (USD)VRBO
Perfect Home For A Family Vacation With All The Amenities
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 13
This professionally designed & decorated vacation home is great for a quiet get away for one or two couples/families or ...
From $499 per night (USD)VRBO
From $480 per night (USD)VRBO
Pet-Friendly Historic Chilmark Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Renovated historic barn (1870). Lofts converted to open bedrooms, private main bedroom, roomy living room/dining/kitchen ...
From $480 per night (USD)VRBO
From $346 per night (USD)Expedia
Private & quaint cabin-style home with wraparound porch - small dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sunset on the Vineyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $346 per night (USD)Expedia
From $665 per night (USD)VRBO
Spacious family house, short walk to the Lagoon & close to Oak Bluffs center
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The 'Anchor Inn' on Carole Avenue is the perfect spot for your family to relax and enjoy the Vineyard! The home is a 4 ...
From $665 per night (USD)VRBO
From $296 per night (USD)VRBO
Updated Oak Bluffs home! Close to everything!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This home was updated in 2023! Beautiful detached 2 bedroom within walking distance to the center of Oak Bluffs. The ext ...
From $296 per night (USD)VRBO
From $757 per night (USD)VRBO
Humble Abode /Charming Cottage Near Long point Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedroom, 2 full bath family friendly home down our road from Long Point Beach and pond (great swimming and paddling, c ...
From $757 per night (USD)VRBO
From $745 per night (USD)VRBO
Katama Bay - South Beach home - walk to beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Let your vacation begin! A 3 bedroom, 2 1/2 bath home that could sleep up to 8 comfortably on a quiet cul-de-sac off of ...
From $745 per night (USD)VRBO
From $974 per night (USD)VRBO
Immaculate Katama 4BR house with home theater and large yard
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy this spacious, sunny home on a quiet street just steps from the bike path and about 1 mile from South Beach and Ed ...
From $974 per night (USD)VRBO
From $670 per night (USD)VRBO
OB Watrfront 4+ BR. Quiet/Walk to Town. Beachy, classic, great ocean/pond views.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Best of everything: We are located on the back side of Farm Pond, which overlooks Harthaven, Nantucket Sound, and Chappa ...
From $670 per night (USD)VRBO
From $1882 per night (USD)VRBO
\"The Carousel House\" - Ocean Park - Featured in New York Times
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
This house, built in 1865, was featured in the New York Times article on Oak Bluffs, 'The President Was Here (Grant, Tha ...
From $1882 per night (USD)VRBO
From $622 per night (USD)VRBO
Charming Chilmark beach house with private Abel's Hill beach access
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Lovely house at the top of Abel's Hill with access to private Abels' Hill Beach a half mile away. The house is wonderful ...
From $622 per night (USD)VRBO
From $791 per night (USD)VRBO
Home has undergone a major renovation - Everything new! Short distance to town!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
SPECIAL NOTE: Rental is Tax Exempt with a stay over 32 days! We hope that you would find it most appealing as our prio ...
From $791 per night (USD)VRBO
From $628 per night (USD)Expedia
Newly Renovated Martha's Vineyard Vacation Rental!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hop on the bike path for a short jaunt to popular South Beach or walk to historic Edgartown from this conveniently locat ...
From $628 per night (USD)Expedia