WINTER RENTAL. 4 bedroom, 2.5 bath Cape within walking distance of Woods Hole village and waterfront, Martha's Vineyard ferry, MBL, and WHOI. Near beaches, shopping, and Shining Sea Bikeway. House is furnished and fully-equipped. Spacious first floor living room with gas fireplace and dining room; 3 bedrooms and 1 full bath; half bath off the main bedroom. Bedroom/full bath and large room with

Ryan Mann Sotheby's International Realty

Oceanfront Escape in Exclusive Penzance Point - A Classic Cape Cod Summer Awaits. Nestled in the private enclave of Penzance Point, this nostalgic Cape offers a rare blend of seclusion, charm, and sweeping water views. This spacious oceanfront haven hosts 5 bedrooms and 3.5 baths, with stunning vistas from every room and an expansive deck that wraps the home, drawing you into the natural beauty

Danielle Rokosz Sotheby's International Realty

Oceanfront Escape in Exclusive Penzance Point - A Classic Cape Cod home awaits. Nestled in the private enclave of Penzance Point, this nostalgic Cape offers a rare blend of seclusion, charm, and sweeping water views. This spacious oceanfront haven boasts 5 bedrooms and 3.5 baths, with stunning vistas from every room and an expansive deck that wraps the home, drawing you into the natural beauty of

Danielle Rokosz Sotheby's International Realty

Year-Round Rental-Stately four-bedroom, 3.5-bath Colonial with an attached two-car garage offers over 3,000 sq. ft. of beautifully maintained living space, plenty of room for everyone. The main level features a well-appointed kitchen with a breakfast/lunch bar and adjoining den for casual dining, a formal dining room ideal for entertaining, and a bright solarium filled with natural light. A small

John Bowen Bowen Real Estate of Cape Cod

Woods Hole WINTER RENTAL. 3 bedroom, 3.5 bath home available starting October 15th 2025 through June 30th 2026.Beautifully built in 2021, this home is conveniently located near the Village of Woods Hole and local beaches. The first floor features a bright living room, an office space, and an open kitchen and dining area. On the second floor, you'll find three bedrooms, each with its own ensuite

Kimberly Stockwell Ermine Lovell Real Estate, LLC

WOODS HOLE WINTER RENTAL -Available November 1, 2025 through May 31, 2026. Charming wood-shingled home built in the late 1800s, ideally located in the heart of Woods Hole Village with convenient access to town and Steamship ferry service to Martha's Vineyard. The first floor features two living spaces, an eat-in kitchen, a half bath, and a laundry area with pantry. Upstairs, you'll find three

Sue Giordano Ermine Lovell Real Estate, LLC

OFF SEASON RENTAL AT ROUND HILL..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 now through May 31st, 2025, this fully furnished property offers a unique chance to experience coastal living at its

Fatima Simas Anne Whiting Real Estate

Tucked away in a desirable Woods Hole neighborhood, 44 Nobska Road offers a unique combination of privacy, tranquility, and close proximity to coastal amenities. Located near the Shining Sea Bikeway and Nobska Beach, this contemporary-style residence provides an opportunity to enjoy Cape Cod living in a peaceful setting.The home features vaulted, beamed ceilings, pecky cypress wood details, and

Ryan Mann Sotheby's International Realty

Woods Hole furnished rental. This modern home was built in 2024 with attention to detail & high-end finishes. Enjoy the proximity to Woods Hole Village offering world class restaurants, artisan shopping, boating, fishing, and tennis. Spend time exploring Martha's Vineyard, the ferry is a short distance from this home. Also close by is the Woods Hole entrance to the Shining Sea Bike Path a

Irene O'Connell Sotheby's International Realty

NEARLY SOLD OUT - LATE SUMMER RENTALS AVAILABLE, INCLUDING LABOR DAY WEEKEND at $5,000/week (plus MA tax). This beautiful expansive home sleeps 9-10+ comfortably and is steps from the beach and scenic "Shining Sea Bikeway". Offering a picturesque path to Woods Hole and Falmouth Center (each 2 miles away) and extending to North Falmouth, you'll find numerous public beaches, shopping, restaurants,

Robert Katz Coldwell Banker Realty - Sudbury

Stunning 4 bedroom, 2 bath colonial home that has been completely renovated with high end finishes throughout. Beautiful wood floors, spacious areas for entertaining and a lovely patio makes this the perfect home to rent at any time during the year. Just a short stroll to the beach and everything Woods Hole offers, this home is ready for your vacation getaway.

Burton + Burton Sotheby's International Realty

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and relaxing

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

Karen Overtoom Karen M. Overtoom R.E.

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.

Karen Overtoom Karen M. Overtoom R.E.

PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

Karen Overtoom Karen M. Overtoom R.E.

Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

Karen Overtoom Karen M. Overtoom R.E.

THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through open

Karen Overtoom Karen M. Overtoom R.E.

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

Karen Overtoom Karen M. Overtoom R.E.

THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

Karen Overtoom Karen M. Overtoom R.E.

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and master

Karen Overtoom Karen M. Overtoom R.E.

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Relax and enjoy this majestic estate you will call home during your stay. This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation

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 $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

Karen Overtoom Karen M. Overtoom R.E.

Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,725.. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming rustic home is set within Seven Gates Farm in West Tisbury. Walk down your own path to a beautiful private association beach. There are shared tennis courts and miles of walking trails.

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY. The weekly price in August is $5,000. per week. See website for additional weekly pricing. Mill Pond House is a completely restored 1890s farmhouse on the old Mill Pond in historic West Tisbury. Remodeled by the present owner, an interior designer, it is beautifully appointed with antiques and charming accessories. An old pine floor and columns add to the

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced proportions

Karen Overtoom Karen M. Overtoom R.E.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large

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.