WESTPORT RIVERFRONT WINTER RENTAL - This fabulous two (2) bedroom winter rental is available October 15, 2025 - May 15, 2026. It comes with sensational winter sunsets almost guaranteed! The ever present river view is "wicked awesome" as they say! The master bedroom has a queen bed and the second bedroom has 2 twins. There are solar panels to help keep the electric cost down or eliminated;

John Gifford Even Keel Realty, Inc.

weekly rental The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt not to long ago it has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a chefs Kitchen, living room ,dining area and fireplace area. Walk out the

Bryan Hummel Commonwealth Realty Group

DOG FRIENDLY WINTER RENTAL IN SOUTH DARTMOUTH - This furnished home is next door to Demarest Lloyd State Park which says a lot about the beauty of the area. It is available for rent until June 15th. The home has 4 bedrooms but 3 of them can be isolated so as to lower the heating bill if so desired. The back yard overlooks George's Pond and therefore wreaks of natural bird habitat and

John Gifford Even Keel Realty, Inc.

Discover the charm of this quintessential New England farm home, perfectly situated off the main road but still close to town and local beaches. This newer meticulously maintained home features 3 spacious bedrooms, 3 bathrooms, and new high end furnishings. Guests will also enjoy ample private outdoor space for relaxing with family and friends. The finished basement is a versatile space, perfect

Jeanne Bettencourt RE/MAX Vantage

Enjoy the panoramic views of Buzzards Bay and the Elizabeth Islands from this off season rental. This spacious beautifully appointed 3-bedroom, 3-bath home is a rare rental opportunity in the exclusive guard-gated community of Round Hill. Available from October 1st through May 31st, 2025, this fully furnished property offers a unique chance to experience coastal living at its finest. Wake up to

Fatima Simas Anne Whiting Real Estate

Exceptional ,fully furnished, winter rental located in South Dartmouth. Close to Padanaram Village, this property is on a tiny cul-de-sac with only one other home. Enjoy amazing views from your main bedroom balcony/deck, rear deck, pool area and more. Each of the 4 bedrooms have a private full bathroom. The first floor bedroom is set up as an office, but has a murphy bed. The first floor offers

Athena Tetrault Lamacchia Realty, Inc

WESTPORT WINTER RENTAL with access to the east branch of the Westport River. Beautiful, well-maintained cottage with many upgrades. Spacious three season sunroom, porch, deck and seasonal water views. Open kitchen and living room area with cathedral ceiling and fan. Quiet neighborhood. Close to the highway, Horseneck Beach, town beaches and Central Village for shopping. Many well known

John Gifford Even Keel Realty, Inc.

This charming Colonial sits on a large private estate lot. The home offers 3 bedrooms and 3 full baths. 1st floor: Kitchen that opens up to an outdoor private deck, living room, den, dining room, full bathroom and a separate laundry area. 2nd floor: Master suite and two additional bedrooms with a full bath. There are two finished rooms in the basement. Home includes the use of a 1 car attached

Lori Pacheco Anne Whiting Real Estate

WINTER WESTPORT RENTAL Ocean views of the Elizabeth Islands and Gooseberry from this very special year round beach house. Within walking distance to the Beach and Audubon Society Wildlife refuge. Architect designed renovation featuring open floor plan. Fully equipped kitchen, dining area with oak hardwoods, living room with built ins and slider to deck. Full bath with large shower on first

Lindsey Bshara-Leviss Salt Marsh Realty Group

WESTPORT POINT WEEKLY SUMMER RENTAL - "Snowden House" overlooks the west branch of the Westport River which empties into nearby Buzzards Bay. The location is off the beaten track but close (enough) to everything else. "Snowdie" is within easy reach of Newport, Providence, and 65 miles from Boston. This beautiful old house is simple and comfortable. What many would lovingly call, "shabby

John Gifford Even Keel Realty, Inc.

WESTPORT POINT WEEKLY SUMMER RENTAL - "Buckingham Palace" is a charming two bedroom true summer cottage with a panoramic view of the Westport River, Atlantic Ocean and the sand dunes of Horseneck Beach. The house is located in the Historic District of Westport Point, a quaint fishing village and port. Stroll through the village and buy lobsters for supper off the boats at the Town Dock. Have

John Gifford Even Keel Realty, Inc.

Weekly Vacation Rental or Year round Lease- "Crow's Nest" - A cozy studio in a high end homeowners association with water views, an ample yard surrounded by stone walls, access to tennis court and to the dock, on the east branch of the Westport River. EV charging station available. Minutes to state and local town beaches, Audubon bird sanctuary, seaside restaurants, brewery, winery, and town

Phyllis Ibbotson Mott & Chace Sotheby's International Realty

WATERVIEW SUMMER WEEKLY RENTAL - This Victorian-era converted carriage house is located in the historic port of Westport Point. It hosts 6 bedrooms and a spectacular river view. It's a perfect place for families to gather for a summer vacation. Walk to the Town Dock and buy your lobsters right off the boat. Also at the Dock, you can enjoy a locally grown Westport Oyster from the local

John Gifford Even Keel Realty, Inc.

Outstanding Summer Rental - Brayton Point Road / Acoaxet / Westport Harbor Area - private, improved waterfront acreage located on Richmond Pond; quiet, dead end road; property fronts on Richmond Pond; easterly & southerly water views over Richmond Pond to barrier beach and Howland Beach; Atlantic Ocean views to Cuttyhunk Island, Gay Head - easy access, walk to Atlantic Ocean beaches; hot

George Collias South Coast Auctions & Realty

Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime location off North Road

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Charming three bedroom cottage set on a hill overlooking a tranquil meadow just 1 & 1/2 miles to Aquinnah Cliffs. Enjoy access to both Philbin and Lobsterville beaches. There is a front and back porch with rocking chairs to take in the landscape and enjoy the breeze. This sunny property is easily accessible as well as peaceful and relaxing. Owner is

Karen Overtoom Karen M. Overtoom R.E.

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoor shower with multiple shower heads to wash off the

Karen Overtoom Karen M. Overtoom R.E.

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Breathtaking water views from this contemporary home located on Menemsha Pond and recently renovated with new kitchen and baths. This four bedroom retreat offers the perfect place to come during the summer months or even enjoy during the shoulder season while sitting by the fire with a warm cup of your favorite hot beverage. PLEASE TAKE NOTE!!!!!THIS IS

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Down a private country road, this bright and breezy post and beam home sits on a 3-acre rolling wooded parcel. With southern views of the Atlantic Ocean, it's just a short drive or bike to Philbin and Lobsterville beaches and Gay Head cliffs. This very Vineyard house offers three levels of living space, chef's kitchen, spacious

Karen Overtoom Karen M. Overtoom R.E.

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms,

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from

Karen Overtoom Karen M. Overtoom R.E.

This family-friendly, three-bedroom retreat on Lighthouse Road in Aquinnah offers all the comforts of home with stunning water views of the Vineyard Sound and the Elizabeth Islands. It is beautifully decorated and nicely furnished. The home features stylish post-and-beam architecture. The main level features cathedral ceilings, wrap-around picture windows and skylights. The main level opens out

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoor shower with multiple shower heads to wash off the sand

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

Karen Overtoom Karen M. Overtoom R.E.

Great water view property in Aquinnah - this immaculate contemporary has that unique combination of a beautifully designed and constructed, year-round home, AND an outstanding view of the Sound and Elizabeth Islands. Not only is the water view property packed with many custom details, but the home's layout is perfect for relaxed living - with a fantastic kitchen open to the dining and living

Karen Overtoom Karen M. Overtoom R.E.

Uniquely designed, 3-bedroom, 2 full bath contemporary home, divided between three floors and set upon an acre of lush grounds with waterviews overlooking Vineyard Sound and the Elizabeth Islands. Privacy enhanced with large tracts of conservation land nearby and walking distance to Lobsterville Beach.

Karen Overtoom Karen M. Overtoom R.E.

SHORT TERM WEEKLY SUMMER RENTAL Enjoy the beach? Enjoy the river? Enjoy a conservation trail? Enjoy a short walk to a restaurant? Enjoy it all when you vacation at 88 Third Street. This totally renovated contemporary 2 bedroom 2 bath cottage offers an open floor plan with a chef's kitchen and views from every room. There's no end to the outdoor enjoyment. Relax on the roof top deck, the

Kathy Santos Residential Properties Ltd.