Vineyard Haven Rentals

Find a variety of Martha’s Vineyard vacation rentals in Vineyard Haven. From waterfront homes to historic houses within walking distance of shops and restaurants, you’ll find the perfect vacation rental for you and your family in Vineyard Haven. Scroll down to browse available Vineyard Haven rentals. You may also be interested in viewing all vacation rentals on the Vineyard.

VINEYARD HAVEN (TISBURY) is the unofficial gateway town of the island, with a deep commercial harbor dating back to the sail ships of colonial times. It’s the only town with ferry service to and from the mainland, year-round. That year-round vitality extends to Main Street shopping and the residential neighborhoods beyond. Vineyard Haven attracts many seasonal visitors and residents who enjoy water sports on Lake Tashmoo or Lagoon Pond, the convenience of the Mink Meadows Golf Course, or relaxing evenings of theatre or dining in town. Learn more about Vineyard Haven.

Vineyard Haven Vacation Rentals

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26 Davis Street

Vineyard Haven, MA26 Davis Street

Price$799,000

Est. Mortgage: $/month

MLS ID 37261

  • Residential
  • Square Feet 1100
  • Bedrooms 2
  • Bathrooms 1
  • Acreage 0.9162

LOCATION, LOCATION! Perched upon a slightly rolling hill sits this Cozy 2 Bedroom Home that is a short walk to Town and Ferry. Thoughtful open floor plan with fir hardwood flooring that offers the convenience of one floor living. Gas fireplace, two great size bedrooms and a bathroom with a walk in shower. A three season sun porch that overlooks a lovely patio, garden and expansive yard. Just off the sun porch you can enjoy your morning coffee on the spacious deck overlooking the tree tops. A four bedroom septic, walkout basement and almost an acre lot make this a UNIQUE OPPORTUNITY for possible expansion to add additional bedrooms or possible guest house with building department approval. VERY EASY TO SHOW.....

Listed by Island Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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65 State Road

Vineyard Haven, MA65 State Road

Price$1,100,000

Est. Mortgage: $/month

MLS ID 37274

  • Residential
  • Square Feet 1602
  • Bedrooms 4
  • Bathrooms 1
  • Half Bath 1

This is a fantastic opportunity to own one of Martha's Vineyard's iconic business locations. This charming in-town Victorian home with retail space and outbuildings has many possibilities for a home-based business. Four well-appointed bedrooms and stylish bath on the second floor have functioned as a popular Air BNB, booked through September. The first floor houses a bustling business with several rooms designed for display and studio space. There is also a charming kitchen with a bay window and pantry as well as a half bath. A full basement provides a laundry room and plenty of storage space. The latticed garage framed by gardens has been used as an inviting second retail space. An outdoor shower, inventive summer salon, plenty of parking and private patio top off this uniquely appealing property. Showings will need one day notice. A Fall closing is preferred while the owner is planning her retirement.

Listed by Tashmoo Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Mud Puddle Road

MLS ID 37244

  • Commercial
  • Village Central
  • Location 41.446426,-70.610336

Your Opportunity to be in the B2 District. Start your business/move your existing one to this 1.04 Acre Parcel of Raw Land ~ an open canvas for your business design/build. Located just minutes from the Steamship Authority. Recent Land Division approved by the Tisbury Planning Board. Being sold "as is". Sellers do not make any representations or provide warranties regarding the potential use of the Property. Buyers are responsible to preform their own due diligence. Buyer is responsible for bringing in utilities and for Town Permits. The abutting Lyle Lane Parcel is for sale separately, Purchase both and have 2.18 Acres in the B2 Commercial Property Zone. Many Options for this Location!!!

Listed by O'Loughlin, Janna of Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Lyle Lane

MLS ID 37242

  • Commercial
  • Village Central
  • Location 41.448233,-70.609981

Your Opportunity to be in the B2 District. Start your business/move your existing one to this 1.14 Acre level Parcel of Raw Land ~ an open canvas for your business design/build. Located just minutes from the Steamship Authority! Recent division approved by the Tisbury Planning Board. Being sold "as is". Sellers do not make any representations or provide warranties regarding the potential use of the Property. Buyers are responsible to preform their own due diligence. Buyer is responsible for bringing in utilities and for Town Permits. The abutting Mud Puddle Road Parcel is for sale separately, Purchase together and have 2.18 Acres in the B2 Commercial Property Zone! Many options for this Location!

Listed by O'Loughlin, Janna of Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Lyle Lane/0 Mud Puddle

MLS ID 37259

  • Land
  • Village Central
  • Acreage 2.18

Imagine your possibilities! Start your business/move your existing one to this 2.18 Acre Parcel of Commercially Zoned Land! Located just minutes from the Vineyard Haven Steamship Authority! A perfect spot for your business or residence, mixed use! Close to Town ~ This Land Listing includes two Lots- Lyle Lane & Mud Puddle Road. A 2.18 Acre parcel in the Commercial Property Zone B2. The recent division approved by the Tisbury Planing Board. Being sold "as is". Sellers do not make any representations or provide warranties regarding the potential use of the Property. Buyers are responsible to preform their own due diligence. Buyer is responsible for bringing in utilities and for Town Permits. Many options for this location!

Listed by Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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81 Edgartown Vineyard Haven Road

MLS ID 37190

  • Multi-Family
  • Village Central
  • Bedrooms 3
  • Bathrooms 2
  • Half Bath 1

Centrally located with easy access to town and transportation, this multi-house property makes for a great live/work/investment opportunity. The main older Victorian home with 2+ bedrooms and 1-1/2 baths has some nice architectural features, an enclosed porch, back deck, full basment and large back yard and separate parking. The guest house is set privately to the rear of the property has 3 bedrooms and 1 full bath and it too has a very large yard and plenty of parking and shed. There is also an oversized 4 car garage with extra high ceilings between the main and guest houses. Excellent rental history.

Listed by Martha's Vineyard Island-Wide Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28 Church Street

Vineyard Haven, MA28 Church Street

Price$1,450,000

Est. Mortgage: $/month

MLS ID 37103

  • Residential
  • Village Downtown
  • Square Feet 1717
  • Bedrooms 3
  • Bathrooms 2

Built in 1880 by the whaling captain David Porter West, this fabulously restored In-Town Greek Revival home with classic shutters, sconces, and a white picket fence, located in the William Street Historic District awaits you! The home you have been waiting for is being sold furnished and ready for you to move right in. The location cannot be more ideal, steps from the MV Playhouse, restaurants, shops, library, and the ferry. Looking for entertainment - enjoy concerts at the bandstand in Owen Park, bask in the sun at the public beach, or launch a boat at the landing for a day on the water. Lovingly maintained, keeping the old world charm, with original trim, molding, and wide heart-pine floors, this classic antique has 3 comfortable bedrooms, including a master suite, 2 ½ baths, and 4 wood-burning fireplaces that add to the character. The formal living room with a fireplace is at the front of the house and is bathed in natural light. A more frequently used open living room, also with a fireplace and the dining room, are in the middle of the house. The kitchen with a third fireplace and swinging pot rack and beehive oven, functional mudroom/laundry area, and powder room are cleverly at the back of the house. The staircase is at the front entrance and leads to the second floor. The fourth fireplace is in the front bedroom, with another bedroom, full bath, and a master suite that occupies the second floor. The back patio, landscaping, and a garage complete this remarkable property. Easy to show.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

77 Checamo Road

Vineyard Haven, MA77 Checamo Road

Price$1,350,000

Est. Mortgage: $/month

MLS ID 37169

  • Residential
  • Village South
  • Square Feet 2800
  • Bedrooms 3
  • Bathrooms 3

This Modern, contemporary home is privately sited and centrally located on almost 5 acres of gorgeous treed land. Much of it has been cleared but there is more if ytou want to farm or oprn up some pastures. With miles of walking and horseback riding trails adjacent to the property, this house is perfect for outdoor activities. This 3 bedroom, 4 bath home has many unique details and improvements to the design that make it both comfortable and efficient. Some of it's features include super insulation, radiant floor heat underneat quarter sawn oak floors, stone fireplace, an art room, finished basement, two car garage, loft area, office space and a sunroom for extended living.While this homew lists at 2800 square feet with the finished bonus spaces it comes out closer to 3500 square feet. First floor master makes for easy living with a chefs kitchen with granite and a sub zero fridge.

Listed by Feiner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5 Village Court

Vineyard Haven, MA5 Village Court

Price$435,000

Est. Mortgage: $/month

MLS ID 37201

  • Condominium
  • Village Central
  • Square Feet 658
  • Bedrooms 2
  • Bathrooms 1

Two bedroom, one bath second floor condo centrally located in Vineyard Haven off of State Road. Wood floors in kitchen/dining and the living room, with carpeting in the two bedrooms. Both bedrooms have closets. Full bath has tile floor. The main deck leading into the house has double doors and features an outdoor shower. There is also a small entryway deck leading to the master bedroom. Washer/dryer. New water heater July 2020. Under porch storage area/utility room. This condo is a great place for someone looking for an opportunity to own on Martha's Vineyard! Very easy to show. Agent is owner.

Listed by Match Point Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

733 Main Street

Vineyard Haven, MA733 Main Street

Price$5,890,000

Est. Mortgage: $/month

MLS ID 37140

  • Residential
  • Village West Chop
  • Square Feet 2581
  • Bedrooms 4
  • Bathrooms 3

VIEWS! VIEWS! VIEWS! Completion date for this 4 bedroom West Chop beauty is mid October 2020 and can be sold turnkey. Enjoy spectacular views from 885 square feet of decking and porch overlooking Sheriff's Meadows and the Vineyard Sound. What could be better than living space and dining outside on a pristine deck. With 120 feet of private beach, you will not find better swimming and boat activity on the island. All your amenities are here including a great outside shower, built in grill area with piped propane, mudroom to wash off the sand, and countless spaces outside to read a good book or to dine! First floor master suite with fantastic sunrises and sweeping water views. Combination kitchen and dining, inside or out, plus a living room viewing a 42 foot long deck with the Sound beyond. Upstairs, another master suite with picturesque Sheriff Meadow views, and a porch to enjoy early morning sunrises and coffee. Another 2 bedrooms and full bath plus a sitting area round out the spectacular 2nd floor. This house is ready for the discriminating buyer looking for that move-in ready home, furniture to be negotiated separately. This ideal location is near the 83 acre West Chop Woods, Mink Meadows Golf Club, the West Chop Club, and the Vineyard Haven Yacht Club. Rarely is there a waterfront in this area with such dramatic views and a total renovation. Don't miss your opportunity to have your own slice of paradise anytime you want to escape to the Vineyard or year-round living! Please call listing office for floor plans and renderings from Squash Meadow.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1140 State Road

Vineyard Haven, MA1140 State Road

Price$1,150,000

Est. Mortgage: $/month

MLS ID 37126

  • Residential
  • Village South
  • Square Feet 1284
  • Bedrooms 3
  • Bathrooms 1

Tranquility and privacy in Vineyard haven. Located in a park-like setting abutting both agricultural and conservation lands, this classic 3 bedroom home with 1 1/2 baths is available for the first time in more than a half century. A short drive or bike to Vineyard Haven you can walk to the Scottish Bakehouse for your morning coffee and breakfast. Abutting the landbank there are miles of trails out the back door. This is a destination home that will delight in its simplicity and has plenty of room for expansion.

Listed by Feiner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

103 Main Street

Vineyard Haven, MA103 Main Street

Price$13,500,000

Est. Mortgage: $/month

MLS ID 37110

  • Residential
  • Village West Chop
  • Square Feet 7046
  • Bedrooms 5
  • Bathrooms 4

THE ULTIMATE WATERFRONT RETREAT - The Vineyard has always been the place to go for R&R, and if you needed it in the past, you certainly need it now. It is the oasis of beauty and tranquility in a vintage community. This property offers the best of the Island. Located on Vineyard Haven Harbor, the home sits on a large 1.7A parcel of land, which provides privacy, spectacular views of harbor activity, yet steps away from the Village for your morning coffee, afternoon shopping, and dinner and theater in the evening. A unique feature is proximity to the ferry to come to and leave the Island easily. Think of it - the kids who will probably be with you a lot more, Mom and Dad, who will visit, and the family workforce can easily use the Vineyard home as "operation center," adjusting to the new lifestyle perfectly. Designed by premier architect Patrick Ahearn, with 7,045 sf, the home is warm and friendly with space to accommodate everyone's needs. The large kitchen with sitting room and fireplace opens to a screened porch. A dramatic stone fireplace is the focal point of the sitting area on the porch with generous room for dining for twelve with views of Harbor activity. This space is the hub of the house. There is a large, quiet office on the first floor for serious work along with a smaller office space off the kitchen. A grand formal dining room with a fireplace and living room is designed for special occasions. Another all-season sun porch on the first floor provides additional space for a variety of activities. The informal and formal areas connect with an outdoor patio. The master bedroom suite with a sitting area occupies the south wing of the second floor and is cleverly separated from the activity of the household. Three more bedrooms are in the north wing of the house. Another expansive deck connects both wings. The views from the first floor are spectacular, and they become panoramic and magnificent on the second floor. There is a guest suite over the two car garage which can be accessed from the outside or the adjoining deck on the second floor. The piece de resistance is the widow's walk offering the most brilliant views. The terraced pool and built-in outside grill overlooking the Harbor complete this perfect Vineyard home.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details