Vacation Rentals

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Private Water Front 6 Bedroom W/Dock Sits in The Shadow of The East Chop Lighthouse

233 East Chop Drive, Oak Bluffs, MA 02557

InternalID PROP-MARR

  • Non-MLS Vacation Rentals
  • Village East Chop
  • Summer Rental
  • Title Harbor-front Delight
  • Location Oak Bluffs

This beautifully remodeled East Chop home is the ideal family getaway. A traditional Victorian beauty modernly updated for open family living.  Many large spots for gathering as well as private nooks for quiet reflection. With  expansive water views of Vineyard Sound and Cape Cod beyond, the ferries and boat travel alone will mesmerize. The house is elegantly appointed in traditional Vineyard beach style with all the comforts and amenities of a fully equipped vacation home. 5 Bedrooms in the main house with a downstairs master and a separate guest suite known as the Crow's Nest for guests who need a more autonomous experience. Upstairs are the final 4 bedrooms, baths, and of course more views. The sunporch will surely be the favorite spot for gathering but the large front yard and private dock will please the sun lovers and ocean lovers alike. Of course an doutdoor shower and everything you may need for your Vineyard vacation.

Listed by Breakwater MV

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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Water View- Historic East Chop

21 Mill Square Road, Oak Bluffs, MA 02557

Rental Price$11,000

InternalID PROP-YOUN

  • Non-MLS Vacation Rentals
  • Location Oak Bluffs
  • Address 21 Mill Squre
  • Bathroom 4
  • Maximum Occupants 10

A gorgeously renovated East Chop Victorian cottage in a fabulous location, with expansive views of Nantucket Sound. Wrap around porch facing a gently sloping front yard, just steps from the beach, ocean, harbor and town, make this the quintessential vacation rental. Back yard includes patio, 2-car garage, and driveway with parking for multiple cars. Its water views from all levels and proximity to the town of Oak Bluffs make it one of the most popular locations on East Chop.

Listed by Breakwater MV

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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SUMMER RENTAL: EAST CHOP ENCLAVE

112 Park Street, Oak Bluffs, MA 02557

InternalID PROP-SCHWR

  • Non-MLS Vacation Rentals
  • Village Oak Bluffs
  • Bathroom 3
  • Bedrooms 4
  • Sleeps 8

[FOR RENT] This magnificent 1920’s East Chop cottage has been extensively redesigned, refurbished and expanded to allow friends and families to enjoy unsurpassed accommodations along with rare double views of both Nantucket Sound and neighboring Crystal Lake. Complemented with a huge wrap around deck and Covered Dining Rotunda, this home provides a desirable location and setting for a memorable Vineyard Vacation. Completed in September 2014, this remarkable vacation home will be offered to discerning vacationers for the first time in 2015. Nestled on a large double lot in a serene enclave of East Chop, Oak Bluffs, your privacy and comfort is assured as you spend time luxuriating both indoors and out. Comprehensive furniture detailing, new luxurious bedding, refinished original hardwood floors, modern bathrooms and a completely remodeled floor to ceiling kitchen preserve the olde world charm you expect, but also provide new and modern conveniences you need and want on your stress free Vineyard vacation. New stainless appliances, new granite counter tops and kitchen cupboards, family style farm dining table and an incorporated sun porch provide a sensualist twist to meal time. French doors invite you to eat outside, take advantage of the expansive porch with three distinctive seating/eating areas where you’ll experience the gentle cooling ocean breezes. All stress simply dissolves away as you relax and watch the boats sail by and enjoy the spectacular sunsets. The comfortable living room features swivel chairs, a beach stone fireplace and oversized picture window. Four generous bedrooms (one on the main floor) feature either Twin, Queen or King sized beds with sleeping for eight (8). The Master Bedroom sports an antique King Brass Bed, private ensuite with double vanity, claw foot soaker tub and separate shower. Apart from the historic Brass Bed Head and Footboards, all beds have new luxury plush mattresses and frames. The additional two totally new bathrooms have marble vanities and are completely remodeled with modern tiled floors and showers (and hand shower heads). The wrap around porch is protected with a flowing roof line and architectural overhangs. You will be able to find sun or shade all day long. You will also treasure the plentiful antique wicker deck furniture, a considerable outdoor dining table, covered dining rotunda and convenient gas fired BBQ. Weekly: $9,200

Listed by Breakwater MV

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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SUMMER RENTAL: ELEGANCE ON EAST CHOP

15 Mill Square Road, Oak Bluffs, MA 02557

InternalID PROP-MARLW

  • Non-MLS Vacation Rentals
  • Village Oak Bluffs
  • Summer Rental
  • Bathroom 3
  • Maximum Occupants 10

[FOR RENT] Beautiful East Chop home with easy access to the beach, tennis, the lighthouse, and Oak Bluffs town. The Chef’s kitchen has every amenity you could desire and is perfect for dining. The house has a built-in sound system for dinner parties. The downstairs master has an attached bath with a private screened-in porch. The exterior of the home boasts a wrap-around farmer’s porch — it’s rocking and Addirondack chairs ready for your holiday party. This Summer Home is air-conditioned, decorated in classic Vineyard style and has 5 bedrooms and 3 bathrooms. Get your Summer Island Memories started! Weekly: $8,500

Listed by Breakwater MV

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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Captain Spring House

12 Spring Street, Vineyard Haven, MA 02568

InternalID PROP-CHAMC

  • Non-MLS Vacation Rentals
  • Village Downtown
  • Summer Rental
  • Summer Rental Price $7,990
  • Title Captain Spring House

With sweeping views of Vineyard Haven Harbor, this recently built, in-town luxury home, combines commanding water views with four levels of sophisticated and stylish living space, including two roof top decks, Home Theater, tournament Pool Room, Penthouse Lounge, and more.   The main floor of Captain Spring House features an open Great Room designed for entertaining, with Living and Dining Areas, plus a large Gourmet Kitchen.    The fully-equipped Chef's Kitchen features marble countertops, grand prep island/breakfast bar with seating for eight, Wolf and Sub Zero stainless appliances, two farmer sinks, double dishwashers, and wine refrigerator. There are hardwood floors and high ceilings throughout the home.   All four bedrooms feature full marble baths with tub and shower, and flat screen TVs. The second floor Master Suite also has a glass walk-in shower and whirlpool with harbor views.   The third floor Penthouse Lounge features phenomenal views, sectional seating, wet bar, and refrigerators. Best of all, walk out onto two large mahogany sun decks that face the harbor. (One also has an outdoor shower.)   The lower level features both a Home Theater and a Pool Room Lounge. There is a tournament pool table and a fully-equipped wet bar. Captain Spring House sits quietly on a side street, just steps from downtown Vineyard Haven with its charming Main Street, restaurants, shops, beach, and ferry which is only 2 blocks away.

Listed by Breakwater MV

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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The Edgartown Pond House

68 Turkeyland Cove Road, Edgartown, MA 02539

InternalID PROP-ELLIE

  • Non-MLS Vacation Rentals
  • Village Katama
  • Summer Rental
  • Summer Rental Price $7,000
  • Title Edgartown Pond House

Perfectly situated on Edgartown Great Pond is this  charming three bedroom, three bath Vineyard Cape style home. This home provides access to a private section of South Beach. Rent or bring your kayaks and paddle over to South Beach with your friends and family for the afternoon. Also you can enjoy relaxing by the in-ground pool or have cocktails on the deck. Close to Edgartown Village this Vineyard home has all you need for a pleasant vacation.

Listed by Breakwater MV

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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Downtown Oak Bluffs 6 Bedroom Fanciful Cottage

51 Pequot, Oak Bluffs, MA 02557

InternalID PROP-WATEM

  • Non-MLS Vacation Rentals
  • Village Oak Bluffs
  • Title Top Cottage
  • Date Available 07/23/2016
  • Location Downtown Oak Bluffs

Location, location, location! This 6 Bedroom 3.5 bath Oak Bluffs home is so close to everything that no vehicle is necessary. Walk on the ferry and walk down Circuit Avenue to this whimsical home where summer memories are made. Commercial grade stainless kitchen appliances and eclectic touches everywhere in this fantastical home allow for fun gatherings and family meals. 6 Bedrooms and 3 full baths mean everyone can enjoy their time here. Walk to the town beach, coffee shops and restaurants, as well as Oak Bluffs many curated boutiques. This home reflects the true fun loving atmosphere of the town of Oak Bluffs and allows you to vacation with extended family and friends. Downtown Oak Bluffs is home to the Flying Horses, the oldest carousel in the United States, as well as many other attractions.

Listed by Breakwater MV

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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Summer Rental- Classic East Chop Modernized

29 Thompson Ave, Oak Bluffs, MA 02557

InternalID PROP-TAYLR

  • Non-MLS Vacation Rentals
  • Summer Rental
  • Location Oak Bluffs
  • Address 29 Thompson Ave
  • Bathroom 3

You will have realized luxury when you are in this home. Perfect for family and friends to entertain or relax. This home is approximately 3,000 square feet, with four bedrooms and three baths. There is a large foyer that flows into a sunken sitting area with floor to ceiling windows and cathedral ceiling and air conditioning. There are multiple sitting and living areas for entertaining and gathering areas for family and friends. Modern kitchen with all the appliances you will need 2 ovens and 2 cook tops. Granite counter tops and stone back splash. Large mahogany deck with table and chairs and built in speakers. Perfectly located on East Chop, a quick walk or bicycle ride into town or to the beach. Enjoy a spacious deck, as well as an outdoor shower. 

Listed by Breakwater MV

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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Oak Bluffs Harbor Home

15 New York Avenue, Oak Bluffs, MA 02557

InternalID PROP-JOHNB

  • Non-MLS Vacation Rentals
  • Village Downtown
  • Summer Rental
  • Location Oak Bluffs Harbor
  • Address 15 New York Avenue

Views of the harbor, walk to town, close to the beach and new! Does not get much better than this new Oak Bluffs rental home!  Recently rebuilt with four bedrooms and three full bathrooms, all new appliances and furniture. Beautiful appointed with everything you need for a relaxing vacation on Martha'sVineyard.  The home includes wet bar, entertainment room, living room with fireplace and views of the Oak Bluffs Harbor. Come and make new memories at this wonderful home.  All four bedrooms are located on the second floor, two bedrooms with king beds and two bedrooms with two twin beds. 

Listed by Breakwater MV

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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SUMMER RENTAL: FAMILY-FRIENDLY COTTAGE

19 Plymouth Avenue, Oak Bluffs, MA 02557

InternalID PROP-SHAFM

  • Non-MLS Vacation Rentals
  • Village Oak Bluffs
  • Bathroom 2
  • Maximum Occupants 12
  • Bedrooms 6

[FOR RENT] Enjoy views of the ocean and harbor in this lovely East Chop cottage that can house 12 guests! This home was built in 1890 and has been fully renovated. With six bedrooms, four bathrooms, a lovely outdoor shower and new kitchen/appliances, it is perfect for a long stay on Martha’s Vineyard. There is a beautiful front porch and a back patio, perfect for outdoor activities or dining. The living areas and brick fireplace are excellent for indoor activities on cool evenings. The first floor has a bedroom with a full bed and private half bath. Upstairs there are two large master bedrooms with king beds, one room with two twin beds, and one room with a bunk bed and a twin bed. Then on the 3rd floor, in the tower room, there is a day bed. Weekly: $5,500

Listed by Breakwater MV

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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Lighthouse Views

220 East Chop Drive, Oak Bluffs, MA 02557

InternalID PROP-ROSSJ

  • Non-MLS Vacation Rentals
  • Village East Chop
  • Summer Rental
  • Summer Rental Price $5,500
  • Title Lighthouse Views

  Classically appointed 3 bedroom home with a  huge open concept 2nd floor. Wrap around deck showcases many Vineyard water views. Traditional kitchen and sitting areas allow the beauty of the outdoors to flow in through the floor to ceiling glass "walls".  

Listed by Breakwater MV

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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Summer Rental: Vintage Cottage Beauty

19 Mill Square Road, Oak Bluffs, MA 02557

InternalID PROP-BURNW

  • Non-MLS Vacation Rentals
  • Location East Chop
  • Address 19 Mill Square Road
  • Bathroom 1
  • Bedrooms 5

Spectacular water views will be yours while renting this vintage East Chop cottage. With 5 bedrooms and plenty of space to make your family feel at home. The large lawn is perfect for outside games and activities, including an outdoor shower which is as much enjoyable as it is functional. With your center location, town beaches and the East Chop Lighthouse are all about a 5 minute walk away. This is the perfect island getaway location!  After a day of sun and sand, come home and enjoy the open-to-the-sky, large outdoor shower--a particularly enjoyable experience not to be missed! There are five bedrooms and one a half baths at this property. There is a half bath on the first floor. On the second floor there is a bathroom with a shower only. There is a three bedrooms on the second floor, a Queen bed, a double bed and two twins.  On the third floor there are two additional bedrooms a double bed and a twin bed. 

Listed by Breakwater MV

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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