Falmouth Classifieds > Housing > Vacation Rentals

This is a lovely home on Chappaquiddick that was developed over the years to accommodate multiple generations and be the center of family vacation fun while maintaining its original charm. Like many of the original Chappaquiddick houses the focus is on the family areas. It has a spectacular view of the outer harbor, East Chop and the Cape (on a clear day). The Main House has 2 living rooms (one...

Situated along Edgartown's inner harbor, this quintessential Vineyard home invites you to relax and watch the glorious sunsets. This well equipped home offers many amenities of modern living including high speed internet. Two kayaks are available for exploring the harbor or Caleb's Pond. Come to this harbor side Chappy gem with your own private beach and your own private dock. Also Caleb's Pond...

This home has been kept in excellent condition, yet still retains a New England colonial/island feel. The house sits on 12 secluded acres with breathtaking views of Katama Bay and the southern shore. It is a waterfront home with 570 feet of private beach on Katama Bay. The distance to the beach is less than 200 yards. NOTE:Please go to the "ISLAND INFO" link on our website and click on "Chappaq...

Beautiful and perfectly located home on top of Chappy's Sampson Hill with heated pool, gardens and jacuzzi, large yard and porches. All beaches and amenities just 1 mile away. Never see traffic or parking jams, your exclusive home is 1 mile to beach. The home centers on old native walking/biking paths connecting to all beaches on Island. PLAY ON CHAPPY's famous beaches during day AND AT NIGHT, ...

Situated with two other houses on a wonderful, 88 acre, waterfront estate of rolling hills and woods with hiking trails, this secluded "Artist's Barn" has a 2 story living room with oak beams, fieldstone fireplace and sliding glass doors overlooking the low deck. A long sweeping meadow leads down to a private beach (rocky) with a little Beach Camp (shared with Main House permission). Loft has q...

Charming Chappaquiddick cottage with distant views of Katama Bay. Relax on the deck after a day at the beach - Katama Bay is only 300 yards away!

In a lovely, rural setting on the island of Chappaquiddick,this is a well appointed home with a large country kitchen that flows to an inviting screened porch and spacious living area. Property abuts and has lovely views of Cape Pogue Bay - great for all types of recreational water activities. Please go to the "ISLAND INFO" link on our website and click on "Chappaquiddick" for additional IMPORT...

THIS IS A WONDERFUL OLD VINEYARD SUMMER HOME ON 88 ACRES OF GLORIOUS PROPERTY FEATURING ROLLING HILLS AND HIKING TRAILS, GROOMED LAWNS, WOODS, PRIVATE BEACHES, BEACH CAMP, AND TENNIS COURT & BASKETBALL BACK BOARD (PROPER FOOTWARE REQUIRED). THE PERFECT GET AWAY SPOT FOR A LARGE GATHERING OF FAMILY AND FRIENDS, OR AN INTIMATE SETTING FOR A CORPORATE MEETING OR RETREAT. IMAGINE THE POSSIBILITIES....

Watch the 4th of July fireworks and spectacular sunsets over the Edgartown Harbor from this bright, light and airy home. This home is set on over two acres surrounded by flower gardens in a very private setting, this casual, easy-to-be-in summer home affords breathtakingly spectacular waterviews from the top deck. There is an inviting, large, enclosed, outdoor shower and flagstone patio. A quic...

A WONDERFUL OLD RAMBLING VINEYARD SUMMER HOME - LIKE A LARGE CAMP WITH AN ECLECTIC MIX OF FURNISHINGS AND ANTIQUES. IT IS SET ON 5.6 ACRES OF YARD, FIELDS & WOODS WITH A SMALL, PRIVATE BEACH. IT IS THE PERFECT SPOT FOR AN INFORMAL SUMMER ESCAPE. COME RELAX, EXERCISE AND ENTERTAIN. TAKE A FIVE MINUTE WALK TO PRIVATE KATAMA BAY BEACH OR TAKE A FIVE MINUTE DRIVE TO WASQUE,AN OCEAN BEACH. Please go...

CONTEMPORARY WITH THREE DECKS THAT GIVE YOU WONDERFUL WATERVIEWS OF EDGARTOWN'S INNER & OUTER HARBOR. RELAX IN THE SAUNA OR ON THE DECKS, WALK DOWN TO THE SANDY PRIVATE ASSOCIATION BEACH,JOG ALONG SCENIC ROADS,OR WALK DOWN TO THE CHAPPY FERRY AND TAKE A 2 MINUTE RIDE TO HISTORIC EDGARTOWN WITH ITS FINE RESTAURANTS, GALLERIES AND SHOPS. A SLIP is available (UP TO 18" BOAT)AVAILABLE AT EXTRA COST...

SET AMOUNG THE TREETOPS ON CHAPPAQUIDDICK'S (AND EDGARTOWN'S) HIGHEST POINT WITH LOVELY DISTANT VIEWS OF THE OCEAN AND NANTUCKET FROM MOST WINDOWS & THE DECK/PORCH, THIS INFORMAL SUMMER HOME IS A PERFECT VACATION SPOT. IT HAS AN OPEN, LIGHT & AIRY DESIGN, MIX OF OLDER & NEW FURNISHINGS, AND A SMALL FULLY EQUIPPED KITCHEN. ALL CHAPPY BEACHES ARE WITHIN 5-10 MIN. DRIVE AWAY! HIKING PATHS ARE EVER...

THIS BEAUTIFULLY BUILT CONTEMPORARY SITS JUST OFF WASQUE ROAD ON A WOODED LOT WITH A LOVELY GARDEN GRACING THE ENTRY TO THE HOUSE. THE ENTRY HALL, GRANTS YOU ACCESS TO ALL THREE BEDROOMS AND THE SCREENED PORCH AND OPEN TERRACE. THE ATTRACTIVE SECOND FLOOR LIVING AREA IS OPEN IN DESIGN AND LOOKS OUT THROUGH GLASS SLIDERS TO A COMFORTABLE DECK AND OFF TOWARD NANTUCKET SOUND. FROM THIS DECK WALK U...

LOVELY OLD FARM HOUSE FULL OF CHARM ON 88 WONDERFUL ACRES OF LAWNS, BEACHES, ROLLING HILLS AND WOODLANDS, AND HIKING TRAILS. SHARED PRIVATE TENNIS COURTS & BASKETBALL HOOP (proper footware required). A STROLL AWAY IS SANDY BEACH AND A BEACH CAMP (THE LATTER USED WITH MAIN HOUSE PERMISSION). WATERVIEW FROM UPSTAIRS COMMODE IS A DELIGHTFUL PLUS. SCREEN PORCH IS PERFECT FOR RELAXING, ENTERTAINING ...

Wonderful, spacious, open & airy contemporary home set on the Wasque plains with great views of Katama Bay & the Atlantic Ocean (walk to both). Spacious kitchen with breakfast counter, cathedral ceilings, skylights, wall to wall carpeting. Large screened porch, open decks. Adjoins acres of conservation land full of natural splendor. 300 yards to Bay beach and a bit farther to the ocean. A beaut...

THIS FORMER WORKSHOP ON TOM'S NECK FARM, HAS BEEN CONVERTED TO A WONDERFUL RUSTIC COTTAGE DECORATED WITH OLD FARM TOOLS. IT SITS ON 70 ACRES OF LAND WITH WOODS, FIELDS, ROLLING HILLS, WALKING TRAILS, CLAMMING POND & A LONG, GLORIOUS SANDY BEACH. WILDFLOWERS & WILDLIFE ABOUND. IT HAS A RATHER WELL EQUIPPED KITCHEN, BUT NO DISHWASHER. GREAT CONVERSATIONS ENSUE AROUND THE SINK WHILE DISHES ARE BEI...

This is an unusual property! A turn of the century Victorian & one of the largest homes on Chappaquiddick that is the essence of summer cottages of a bygone era. The unique tower suite is the highest point on Chappy and was used by the Coast Guard in World War II. The 360 degree breathtaking tower views extend to Nantucket in the East and the Atlantic to the West. The beautiful deck overlooking...

ON THE ISLAND OF CHAPPAQUIDDICK - THIS WONDERFUL, OLDER, CONTEMPORARY SITS ON A BLUFF HAS A 270 DEGREE WATERVIEW AND PRIVATE SAND & ROCK BEACH ACCESSED VIA 40 STEPS. A SPACIOUS LIVING AREA, A GAMEROOM W/POOL TABLE & PINGPONG LOCATED IN THE LOWER LEVEL, A MASTER BEDROOM W/ROOF DECK & SPECTACULAR VIEWS, TWO OTHER COMFORTABLE SLEEPING AREAS (ONE A BEDROOM AND ONE A DEEP, LARGE LOFT WITH VISUAL PRI...

From the second story spacious living area and multiple decks of this wonderful contemporary home you can look across the Wasque Plains, the beach (walking distance!) and the dunes to a 180 degree spectacular water view of the Atlantic and Katama Bay. It is newly renovated and attractively decorated and has an air of casual comfort about it...the perfect vacation spot. The sunsets are magnifice...

WONDERFUL, INFORMAL COTTAGE STYLE HOME WITH ECLECTIC FURNISHINGS OVERLOOKING LARGE, TIDAL SALT POND (GREAT FOR FISHING & CLAMMING!), BARRIER BEACH & OCEAN (WITHIN 10 MINUTE WALKING DISTANCE!). NICE 1ST FLOOR OPEN LIVING AREA AND A 2ND FLOOR SITTING AREA OPENING ONTO DECK FROM WHICH THERE ARE WONDERFUL, RELAXING WATERVIEWS. TWO OSPREY NESTS WITHIN EASY VIEWING DISTANCE OFFER GREAT BIRD WATCHING....