Holiday rentals with a patio in Oak Bluffs

Chadatopia, Quaint cottage retreat at happy hollow

Quaint summer cottage retreat, situated on manicured grounds with multi level Japanese koi ponds and lush perennial flower gardens in a white pine forested magical hollow. One bedroom with extra living area, refreshing outside shower in rear of cottage. Private fenced in lounge area with gas fire table, pathway to clean unique bathroom and private clam shell parking area..Close to town restaurants, shopping and beaches. Private 82 acre spring fed lake with beach rights within walking distance

Bright townhome with private ponds, pickleball

Beautifully furnished condo is centrally located in a park-like setting. This property is perfect for anyone who loves to explore the outdoors or just relax on the private deck at home. The Sengekontacket Assoc. in Oak Bluffs is a desirable waterfront community easily located off the bike path and on the bus route to town. Private amenities include a freshwater pond just 2-min walk down a quiet road; a large saltwater pond about a 10-min walk to a community dock; and tennis/pickleball courts.

Cape Vacation in style! Close to Main St & Beaches

We affectionately call this house 'The Local,' as it sits in the heart of beautiful Falmouth, within short walking distance to the quaint Main St. shops, delectable restaurants, fish markets, entertainment like bowling and axe-throwing (!), and is a short drive to Woods Hole and many of the Cape's most breathtaking beaches along the coast. Great summer or off-season destination, the house is complete with high-end finishes and furnishings to make your vacation especially comfortable. Enjoy!

Cute cottage steps to beach!

Relax & enjoy this beachside cottage just steps away from a private, sandy beach. This two bedroom cottage is an amazing location in the heart of Popponesset. Grill out on the private deck or stroll to the Marketplace for dinner and ice cream. Additional front deck and Juliet balcony with ocean views for relaxing and sipping drinks. Golf, restaurants, and other Cape summertime activities all close by. Note: construction across the street is planned for the spring and summer of 2025

Charming Vineyard Cottage

Enjoy your Vineyard vacation at this charming, sunny cottage centrally located in Vineyard Haven. The home features two queen beds and one bath with a spacious outdoor patio in a natural oasis. A fifteen-minute walk from the Steamship and downtown, this excellent location provides peace and quiet while still connecting you to local public beaches, entertainment, shops, and dining! Perfect for couples, friends or a small family looking to experience all the Vineyard has to offer!

Single Occupancy Oak Bluffs Studio Apartment

Keep it simple in this peaceful studio apartment. We welcome one guest (and small dog) eager to explore all the Vineyard has to offer! Centrally located, you can easily explore Oak Bluffs or Vineyard Haven; each town is less than two miles from this natural oasis. Boasting a private multi-use studio, private entrance, private stone patio, outdoor shower, and access to the fully fenced-in shared backyard, this apartment is perfect for one person and small dogs under 20 lbs.

Wedgewood Cottage (Available Year Round!)

Create memories in this peaceful 4 bedroom 4 ½ bath cottage located one mile from the 1856 Country Store and less than 2 miles from Craigville Beach. The home sits in a residential neighborhood surrounded by trees and gardens. Relax on the deck, grill the day’s catch, or build a fire and enjoy S’mores in the evening. All of Cape Cod is accessible from this vantage point just south of Falmouth Rd (28). Relax with the whole family at this peaceful place to stay.

In town Cozy-Cottage-Glam w/ Fab backyard 2bd/2B

Experience comfort and style at this centrally-located retreat. Leave the car and walk just minutes to the town and beach. Start your day with coffee on the wraparound porch and refresh with an outdoor shower after the beach. The spacious backyard is perfect for BBQs while the kids play, and the fire pit sets the scene for evening wine. Unwind on the LoveSac sectional with your favorite streaming service or sleep soundly on hybrid mattresses for a restful night.”

Ocean Breeze Escape w/ Private Hot Tub – Cape Cod

Escape to a newly renovated Cape Cod beach retreat! Just minutes from scenic beaches, this private home offers 3 inviting bedrooms, a pull-out couch, a first-floor bedroom, an outdoor shower for sandy beach days, and a relaxing hot tub under the stars. Surrounded by tranquil ponds, biking trails, and coastal charm, it's perfect for adventure and relaxation. Easy access to downtown Sandwich, golf courses, and Cape Cod’s top attractions—an ideal seaside escape!