Vacation Rental Homes to Safely Enjoy Martha’s Vineyard this Holiday

Winter Waterfront Oasis on Sengekontacket Pond

Have you ever considered a visit to Martha’s Vineyard for the holidays? Or even a staycation in another home if you’re already here? We know the holidays are going to look a lot different this year but they can still be extra special, and nowhere more so than Martha’s Vineyard. We love the idea of cozying up in a Vineyard vacation rental home, bundling up for a winter walk along the beach, and sipping hot chocolate in an up-Island retreat with no one in sight. Or strolling along North Water Street in Edgartown enjoying all the stately captain's homes potentially blanketed under some winter snow? (This place is gorgeous in the summer but you should see how picturesque it is with a dusting of that pretty white stuff sprinkled on top!)
 
Now’s the time to enjoy the peace and serenity that this season on Martha’s Vineyard allows. For the locals it’s our favorite time of year, a quieter pace, but as beautiful as ever. And now with COVID, we are most appreciative of the vast open space and reduced crowds, which our fall and winter visitors are grateful for too. If you’re looking to retreat to an island hideaway this holiday, here are some lovely homes available for you and your closest family or friends to enjoy, whether you’re coming to stay or just want a change of scenery on-Island. 
 
Traveling to Martha’s Vineyard? Be sure to read the latest COVID safety guidelines here.

Winter Waterfront Oasis on Sengekontacket Pond

Winter Waterfront Oasis on Sengekontacket Pond
If you want: Open space, seclusion and water views
This charming Edgartown home is situated in an idyllic private wooded setting on Sengekontacket Pond, one of the largest salt-water ponds on Martha's Vineyard. The deck looks out over Major's Cove to Felix Neck Sanctuary across the water and Nantucket Sound a mile away. 

Winter Waterfront Oasis on Sengekontacket Pond

Stay warm beside the working fireplace and enjoy the cathedral ceilings in the living, the dining room, and the kitchen. The home is fully furnished with four bedrooms, three of which have water views. The home sits in an association noted for its quiet, safety, and charm.

Stately Captain Spring House by Vineyard Haven Harbor

Stately Captain Spring House by Vineyard Haven Harbor
If you want: Accessibility, entertainment and en-suites for all. 
With sweeping views of Vineyard Haven Harbor, this recently built in-town luxury home combines commanding water views with a sophisticated and stylish living space. 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 that would make Christmas dinner easier than ever! 

Stately Captain Spring House by Vineyard Haven Harbor

All four of the bedrooms feature full marble baths with tub and shower, and flat screen TVs, perfect for a small group of friends to stay together while also having privacy. The views get even better on the third floor Penthouse Lounge boasting two large mahogany sun decks, both of which face the harbor.

View from Stately Captain Spring House by Vineyard Haven Harbor

Then there is the Home Theater and a Pool Room Lounge complete with a tournament pool table. Talk about location! The Captain Spring House sits quietly on a side street, just a block from downtown Vineyard Haven, walking distance to the Steamship Authority Ferry, and local restaurants, and retail shops.

Stately Captain Spring House by Vineyard Haven Harbor

Luxurious South Beach Getaway
If you want: A ton of shared gathering and entertaining space.
This modern farmhouse near South Beach has been luxuriously renovated throughout the Main House, connected Carriage House, and outdoor spaces. The first floor features a hub of interconnected living and entertaining areas, making it the perfect gathering spot for those closest to you. 

Luxurious South Beach Getaway

The chef’s kitchen boasts stainless appliances, granite counters, dining area, and two prep counter/breakfast bars for the enjoyable meals together. The kitchen also opens into the lounge area for easy entertaining, complete with a wine refrigerator and a beverage refrigerator, plus additional seating. With 6 bedrooms and 4.5 baths there’s ample room for everyone!

Luxurious South Beach Getaway kitchen

Luxurious South Beach Getaway

Coastal Contemporary in the Heart of Edgartown Village
 If you want: All that Edgartown has to offer, including grand views.

Coastal Contemporary in the Heart of Edgartown Village

Tucked away in Edgartown Village, this contemporary coastal-style home sits atop a knoll that enjoys water views across Edgartown Harbor. The property includes a four bedroom Main House and a separate one bedroom Guest House suite.

Coastal Contemporary in the Heart of Edgartown Village Crow's Nest

The Main House is bright and open, with many areas for relaxing and entertaining, including living room, sun room, open chef’s kitchen and sitting area, media room, and the third story nautically-inspired crow’s nest with grand views across Edgartown Harbor. The cottage-style Guest House has its own full bath for additional privacy.

Coastal Contemporary in the Heart of Edgartown Village

Captain’s Cottages at the Harbor View Hotel
If you want: A short walk to the Edgartown Lighthouse & all the amenities of a hotel.

Captain’s Cottages at the Harborview Hotel

Sprinkled along a lovely walkway at the Harbor View Hotel, the Captain’s Cottages exude an individual charm fit for a fairy tale. Inside, they display the finest of luxe comfort and amenities. Glossy white, fresh wicker, nautical stripes and upscale furnishings accent a classic New England ambience.

Captain’s Cottages at the Harborview Hotel interior

Varying floor plans offer many options ranging from one to three bedrooms with kitchenettes. There are eight cottages with 28 cottage units. All prize personal privacy with access to all of the resort’s services.

Captain’s Cottages at the Harborview Hotel kitchen

Farm House at Misty Meadows Equine Learning Center
​If you want: A tranquil, rural setting amid a stunning horse farm up-Island. 

The farm at Misty Meadows in West Tisbury.

In the middle of an active horse farm, this elegant and gracious 5000 Sq. Ft home is perfect for a large gathering of family and friends. Misty Meadows Farm sits on 5.5 acres of stunning surroundings including a Gunite pool, extensive gardens, enclosed courtyard with a patio, lawn and deck. This property abuts 20 acres of protected Sheriffs Meadow Property, including Nat's Farm, expanse of field, meadow, oak woods and pasture. The interior of the house is extremely well appointed and comfortable, including an updated Chef's Kitchen, and all the amenities needed to enjoy a rustic retreat for your Martha's Vineyard holiday stay. Interested parties can email Flanders Real Estate at rentals@flandersrealestate.net or call 508-645-2632.

The farm house dining room.

Spacious and sunny showstopper in Katama 
​If you want: Fun-filled family meals and ample entertaining space  

Located in the Katama area of Edgartown.

Surrounded by sliding glass doors and large windows, this light filled house sets the tone for a relaxing Vineyard vacation. The large family room with soaring ceilings is the anchor for this open floor plan with kitchen and dining area setting the mood for fun-filled family meals and entertaining. The decor is crisp and modern with a nod towards our nautical surroundings.  

Spacious and sun-filled contemporary in Katama

This 4 bedroom, 2 and half bath home sleeps 10. It boasts a modern décor, a master bedroom on the first floor, and all the amenities you would need for a vacation on the island, in any season. 

In-town luxury in the heart of Edgartown Village
If you want: Walking distance to downtown Edgartown for holiday shopping and strolling

In-town luxury in the heart of Edgartown Village.

This house offers four luxurious bedrooms, plenty of bathrooms, two dens and a media room. The first floor features a chefs kitchen with easy access to the dining room that leads to the sitting room and porch with views of the backyard and pool. The first floor master is en suite with access to the back porch. Second floor master is also en suite. The remaining two bedrooms with hall bathroom are on the second floor.

Cook up tasty holiday meals in this well equipped Chef's Kitchen.

 Den/office with powder room provides an addition space for guests. In-season pool and hot tub are in the backyard with a private cabana with wet bar, refrigerator and bathroom. This house is just blocks from main street, bike path and all the wonderful shops and restaurants that Edgartown Village has to offer.