Home Vacation Rentals By Owner In Edgartown, MA

Showing 320 Of 327 Vacation Rentals
Slider Thumb
Exceptional(13)

$1372.6

/ Nightly
Private Vacation Home

Ferry tix avail, large yard, walk to town&Morning Glory, on path, bike to beach.

Edgartown, Massachusetts, United States

**FERRY TICKETS AVAILABLE ( 7/4 -7/11, 7/11-7/18, 7/18-7/25, 7/25-8/1, 8/29-9/5)**brRecently renovated and stocked with everything you need for a fun and relaxing island getaway, this 4BR, 3.5Bth is located just a 1/2 mile from downtown Edgartown's shops and restaurants and a short walk to the renowned Morning Glory Farm. Playgrounds, tennis/basketball courts, outdoor gym, walking trails, and the public library are all within half a mile. Bike or drive 3.5 miles to South Beach, 2.5 miles to State Beach, or 1 mile to Fuller Street Beach.brbr-Large open kitchen with center island (seats 4) & pantry br-Dining area (seats 10)br-Living room with wood-burning fireplace overlooks protected farm landbr-Family room with 55 TVbrbrBedrooms/bathrooms:br-Spacious master (king bed) and ensuite updated bathroom br-Queen bedroombr-Bedroom with two twinsbr-Jack and jill bathroombr-Powder/laundry roombrbrAdditional living space - which is attached to the house but has a separate entrance - comes complete with a living room, dining area, kitchenette, and small full bathroom with stand-up shower. The bedroom has one bunk bed and one twin bed and there are three day beds in the living room. This is a great set up as it provides a set of guests with some additional privacy and space from the main house.brbrEnjoy all summer has to offer on the outdoor patio (expanded with new furniture in 2024), outdoor shower/changing room, hammock, lawn games, and gas and charcoal grills.brbrAmenities include wifi, air conditioning, bluetooth speaker, and a storage room full of beach chairs, umbrellas, and boogie boards. This home has been in our family for three decades and we rent it out selectively. It's a perfect rental for a larger family, or for two families who want to vacation together, which is how we have used it over the years ourselves. brbrMassachusetts now charges 9.7% state and local tax on short term rentals. We typically rent Saturday to Saturday.
Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps

Slider Thumb
Exceptional(27)

$2375.34

/ Nightly
Private Vacation Home

Ideal for extended Families, with Pool, Tennis/Pickleball Court, and Guest House

Edgartown, Massachusetts, United States

Charming Vineyard home with guest house easily accommodates large families vacationing together, with many spacious bedrooms and open common areas. AC is available in all bedrooms and living areas. The private in-ground heated pool (20x40 ft.) and tennis/pickleball court offer opportunities to engage and connect through outdoor activities. Enjoy games or relax in the hammock in the back yard. Share a meal on the long back deck (56ft) equipped with two Weber grills. Indoor features include gorgeous, exposed wood with abundant sunlight, generous living areas, and spacious bedrooms to relax and refresh. The first floor offers plenty of shared space for meals, games, and movies, with an inviting sunroom as well as a den, living room, dining room and state of the art kitchen in an open floor plan. brbrSpacious bedrooms, most with multiple beds, provide flexible housing arrangements. The first-floor bedroom (one king bed) adjoins one of two full baths on that floor. The second floor has four bedrooms and two full baths, one en-suite with the master bedroom (king bed). Two second floor bedrooms have two beds in each (queen, twin); the other bedroom has a queen bed. The third floor has a full bath and two spacious bedrooms with 3 beds in each (queen & 2 twins). The attached two-car garage has two bedrooms and a full bath on the second floor, making it the perfect location for a family to have their own space. One bedroom is very spacious with one queen bed and a crib, and the second bedroom has two twin beds. brbrThe guest house to one side of the back yard offers further opportunity for privacy with a comfortable living room, full size kitchen, full bath and laundry, and two bedrooms (queen and twin in each, plus a crib in one) in an open floor plan. brbrIdeally located halfway between Edgartown center and South Beach, this wooded lot strikes a balance between privacy and convenience. Take the bike path running alongside Katama Rd 1 ½ miles down to glorious South Beach to play in the waves and just relax on the beach. Go 1 ½ miles in the other direction to Edgartown center for plentiful shopping and breathtaking views of the harbor. Or just stay at the property and enjoy the many fun and relaxing opportunities offered. Fantastic vacation home for everyone in the family to enjoy!
Bed 11

Bed

Bath 7

Bath

Sleep 20

Sleeps

Slider Thumb
Exceptional(39)

$455.26

/ Nightly
Private Vacation Home

Great Ranch Style Home In Edgartown W/ Gas Grill & Dog Friendly

Edgartown, Massachusetts, United States

Old OrchardbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrGet away to the summer colony of Martha’s Vineyard and change your pace to island time! This island is known for its beauty and grace, drawing visitors from the White House and Hollywood alike. This little gem is the perfect spot for any visitor to call home for the duration of their stay on this wonderful island. Built on an old Apple Orchard that was developed into a small dirt-road neighborhood with a colonial and cozy feel, it makes you imagine you have traveled back in time. Walking up to the home you are greeted by a classic rocker porch where you can spend your mornings. Step inside and you are welcomed to an open concept kitchen-dining-living space that allows you to easily entertain friends and family alike. And should a rainy day try to spoil your stay, you’ll find games, puzzles, books, and movies galore for all ages. You’ll want to come back again to your home away from home!brbrWhat's Nearby:brbrThis home is a 1/4 mile from Cannonball Park, a village green that is routinely decorated by the town for holidays. Across from the park is the library and school playground. Edgartown Golf Club is less than 1/4 mile away, a great place for morning walks. Three-quarters of a mile east you find Edgartown’s Main Street and downtown, including the wharf, harbor, shopping, restaurants, and the Chappaquiddick Ferry. Oak Bluffs downtown and ferry dock are only 6.5 miles away. Take the scenic Beach Road and go over the famous Jaws Bridge only 3 miles away! Vineyard Haven is just over 7.5 miles via the inland route. Be sure to stop at Island Alpaca a half mile past the rotary – a fun place for everyone!brbrThings to Know:brFree WifibrGas GrillbrFull KitchenbrWindow Unit AC'sbrbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 1 vehicle.brThis rental is located on floor 1.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(11)

$635.55

/ Nightly
Private Vacation Home

Charming island cottage near town & beaches

Edgartown, Massachusetts, United States

Edgartown Cozy CornerbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrIf you're seeking a comfortable escape on Martha's Vineyard, look no further than this quaint and spacious cottage in Edgartown, featuring bright and comfortable living areas and a private in-law apartment that can be rented separately. Watch a favorite show or movie on the flatscreen TV, enjoy one of the provided books in the bay window bench, or venture out to the back deck for a little nighttime stargazing.brbrWhat's nearby:brLess than a half-mile away, visit the town of Edgartown, where you'll find art galleries, museums, shops, and local restaurants. Visit Lighthouse Beach, just over a mile from the home, and Edgartown Harbor Light for a day of fun on the sand and nautical sightseeing. Or take the Chappy Ferry across the bay to Chappaquiddick Island for more beaches and daytime adventures.brbrThings to know:brThe main house (Cozy Corner) and the in-law apartment (Little Cozy Corner) can be rented separately as wellbrTwo full kitchens (one with a dishwasher)brOutdoor shower availablebrWood burning fireplace is not for guest use and for aestheticsbrbrParking notes: There is free parking available for 1 vehicle.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(12)

$1064.3

/ Nightly
Private Vacation Home

Inviting home near town and the beach with fast WiFi and private W/D

Edgartown, Massachusetts, United States

Island OasisbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrFind yourself living the island lifestyle in no time when you book a stay at this fantastic Edgartown oasis! Sitting within walking/biking distance from the beach and heart of town, you'll have no trouble getting your fill of sandy toes and local attractions. When you need a bit of groceries, don't hesitate to check out Morning Glory Farm right down the road offering fresh produce and food to whip up at home. Not to mention, the basketball hoop in the driveway, outdoor shower, and plenty of outdoor seating will make any downtime at home base a blast as well!brbrInside, the whole gang can spread out or gather together with ease. The living area will be the hub for entertainment, as a smart TV and plenty of books in the library will keep everyone busy. When everyone builds an appetite, the culinary-inclined guests can get creative in the full kitchen offering plenty of prep space, modern appliances, and ample cookware. Everyone can pack light as well with the washer and dryer available for guest use!brbrIsland Oasis won't last long, so book your next memorable vacation today!brbrTHINGS TO KNOWbrStreaming is available with guests' own accounts.brWood burning fireplace is decorative and not for guest usebrbrParking notes: There is free parking available for 2 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb

$5874.71

/ Nightly
Private Vacation Home

Amazing North Water Edgartown Compound With Pool

Edgartown, Massachusetts, United States

Luxurious Captain's House Compound: A Summer RetreatbrThe Connaught House is nestled in the heart of Edgartown Village on the Captain's Row section of North Water Street, this exquisite Captain's House Compound, complete with a Carriage House and pool, offers an unparalleled luxury experience. It is like your very own private resort. The beautifully renovated home spans three floors, seamlessly blending indoor and outdoor living spaces, allowing each person in your party to have their own favorite place for relaxation, poolside fun, or even (gasp) work.brbrFirst Floor ElegancebrThe first floor showcases three separate gathering areas. A North sitting room, a South sitting room and a large informal family living room with cozy seating and a charming fireplace and TV right off of the large gourmet kitchen. The gourmet kitchen and living area are framed by two walls of glass windows and French doors. The chef's kitchen is a culinary dream, equipped with commercial stainless appliances, a breakfast bar, stone countertops, and a farmer's sink. French doors open from the dining area to a back bluestone patio, perfect for alfresco dining and lounging, with the inviting pool just beyond. The sunlit private dining area is the perfect location for the evening meal.brbrFamily Comfort and EntertainmentbrThe large living room features a comfortable sectional sofa and a large screen TV, surrounded by glass windows and French doors, providing easy access to the patio and pool area.brbrSecond Floor SanctuarybrUpstairs, the deluxe primary bedroom offers an en suite bath and a nearby office area that opens onto a private deck overlooking the pool. Three additional bedrooms are also on this floor, with two sharing a full bath and the fourth boasting its own en suite bath. The third floor presents a spacious bunk room with six twin beds, built-in sofa seating, and a full bath, alongside a game area and French doors leading to a large sun deck with views over the backyard, firepit, and pool area.brbrCarriage House / Pool House / Guest HousebrThe 2024 Carriage House suite is located by the pool and includes a wonderful private bedroom with an en suite bath, as well as a ground-floor game room.brbrOutdoor OasisbrThe large 42 by 18-foot heated pool is surrounded by a bluestone patio, offering ample space for sun loungers. Positioned prominently on historic North Water Street, the compound is just a short stroll from downtown Edgartown's vibrant restaurants, shops, harbor, and lighthouse. The waterfront and harbor are just across the street and are accessible by either Morse St to the North Wharf or Dagget Street to the Memorial Wharf.brbrPool Information: The pool is heated to 82 degrees in July and August, with heating costs included in the rent. For June and September, an additional heating surcharge of $350 per week applies, and $450 per week for May and October if the pool is open. Please inquire for further details.brbrA few words about this listing.brI took all of the photographs with my iPhone 15 ProMax this fall. The light was not great, and the pools (if the property has one) were covered. I tried to get a professional photographer to take them but it was hard to do and coordinate a time when these properties were empty as they are quite busy. brSome of the beds are not even set up yet. This is indicative of how much this owner cares for these properties (we represent five on them) that he is always fixing them up, adding heavy furniture, and making everything super nice. brWhile we have attempted to confirm every detail, there is the possibility that we might have missed something. These are new listings and we are only too human.brIf you have any questions at all about the booking please feel free to ask me about them. I have personally visited each one, and they are all amazing. br brThe Security Deposit is $5,000 or 10% of the rental rate, whichever is higher brThis property is now allowing well-behaved petsbrThe pet fee is $2,500 with an additional $2,500 security depositbrThe cleaning fee to maintain this large compound is based on an estimate of at least $1,250 per stay. This includes all linens with each bed made and the home presented as immaculate. brA full interim cleaning fee of $1,250 is required for multi-week bookings.
Bed 6

Bed

Bath 5

Bath

Sleep 12

Sleeps

Slider Thumb
Exceptional(21)

$1002.1

/ Nightly
Private Vacation Home

Charming home set on private lot with WiFi, sunroom, W/D, & great location

Edgartown, Massachusetts, United States

Pretty on PradabrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrCharming and quaint, this four-bedroom cedar shake home set on a private, wooded lot is your perfect home base for a Martha’s Vineyard vacation. Tucked onto a quiet street between historic downtown Edgartown and Katama (South) Beach, you’ll have easy access to both – and beyond – via nearby bike paths. Both the Nantucket and Cape Cod ferries are an easy drive away as well. In season, start the day by biking a little under a mile over to the Katama Kitchen for a unique breakfast right next to the Katama Airfield, where you can watch small aircraft and biplanes take off and land on a grassy airstrip while you eat. brbrInside, you’ll find a homey living space, outfitted with everything you need for a comfortable stay. The chef will appreciate the full kitchen, and the adjacent dining area can feed the whole crew. The exposed brick, knotty pine ceilings, and wood floors in the main living area create a charming spot to relax while you stream your favorite shows or upload the day’s pics to social media with the in-home Wifi. Keep dinner simple with the gas grill on the deck, or step out to one of Edgartown’s many restaurants. At the end of the day, four bedrooms with a variety of sleeping configurations mean there is room for everyone. brbrTHINGS TO KNOWbrStreaming is available with guest accounts.brbrParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 4

Bed

Bath 1

Bath

Sleep 10

Sleeps

Slider Thumb
Exceptional(28)

$349.16

/ Nightly
Apartment

Cozy in-law suite near Edgartown & the beach with patio, outdoor shower, & AC

Edgartown, Massachusetts, United States

Little Cozy CornerbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis adorable one-bedroom cottage in Edgartown awaits your next Martha's Vineyard getaway! Watch your favorite movie on the flatscreen TV, or venture out to the back deck with a cup of coffee to enjoy the pristine, landscaped yard.brbrWhat's nearby:brLess than a half-mile away, Edgartown boasts art galleries, museums, shops, and local restaurants. Visit Lighthouse Beach, just over a mile from the home, and Edgartown Harbor Light for a day of fun on the sand and nautical sightseeing. Or take the Chappy Ferry across the bay to Chappaquiddick Island for more beaches and daytime adventures.brbrThings to know:brThis listing is for the in-law suite only. The main house can be rented as well, as Cozy Corner; the entire property can be rented as Edgartown Cozy Corner.brCompact full kitchenbrOutdoor showerbrbrParking notes: There is free parking available for 1 vehicle.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(37)

$478.4

/ Nightly
Private Vacation Home

Welcoming island cottage with patio & enclosed yard - close to town & beaches

Edgartown, Massachusetts, United States

Cozy CornerbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEscape to Martha's Vineyard and book your next stay at this adorable cottage in Edgartown, featuring bright and cheerful living spaces. Watch your favorite movie on the flatscreen TV, enjoy one of the provided books in the sunlit bay window bench, or venture out to the back deck to enjoy the pristine, landscaped yard.brbrLess than a half-mile away, visit Edgartown, where you'll find art galleries, museums, shops, and local restaurants. Just a little over a mile from this rental, check out Lighthouse Beach and the Edgartown Harbor Light for a day of fun on the sand and nautical sightseeing. Or take the Chappy Ferry across the bay to Chappaquiddick Island for more beaches and daytime adventures.brbrThings to know:brbrParking notes: There is free parking available for 1 vehicle.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Home Most popular vacation rentals in Edgartown