Fitness-friendly vacation rentals in Chilmark

Private home, secluded 6 acre lot with water view

Come stay at our beautiful home overlooking Onset bay on a 6 acre lot! Under a mile from a resident beach and public golf course and a short drive to many other beaches, Onset Village, Cape Cod Canal fishing, great restaurants, and shopping! Wareham is the gateway to the Cape! This house has 4 beds, 2 full baths, a large kitchen and dining room, a large 4 season room, a living room, a bonus room with a tv and couch and plenty of parking space! It’s the perfect getaway for family and friends!

Modern Cozy Cottage 5 min Walk to Beach

Escape to The Abigail Cottage in historic Sandwich on Cape Cod! This modern beach cottage comfortably fits families and groups. Enjoy peekaboo ocean views from the roof deck and a private, fenced yard. Just a 5 minute walk to the beach, a 9 minute walk to the iconic Sandwich boardwalk, and a 10 minute walk to Treehouse Brewery. Premium amenities include EV charger and Peloton Row with guest login. The Abigail Cottage is filled with curated decor for the perfect cozy cottage Cape Cod getaway.

New Seabury home, private yard, great location

Relax in this updated New Seabury getaway, perfectly located for beach days or wedding weekends -Walk to Popponesset Marketplace, Popponesset Inn, The Lure & The Raw Bar - Great for New Seabury weddings and events - Just 1.5 miles to South Cape Beach - Renovated in 2023 with new siding, furniture, and more - Central AC - Outdoor shower - Backyard with fire pit - Large deck with BBQ and outdoor dining - Fully equipped kitchen with Nespresso machine - Attached garage - Fast WiFi + 2 SMART TVs

"Wharf Cottage" Idyllic Cape in Yarmouth Port

Immerse yourself in this idyllic cottage and amazing gardens - Quintessential Cape Cod at its best. Located north of 6A and across from the water in one of the nicest neighborhoods on Cape Cod you are a stones throw from everything. Walk to the beach up the road. Coffee Shop and three fabulous restaurants just a walk. Or never leave the private back garden featured on the Annual Hydrangea Festival garden tours. This two bedroom cutie awaits. (PS - Not your average vacation rental!!)

New Seabury Retreat. Butchart Gardens' Inspired

A Tranquil Escape in New Seabury 5-Bedroom Cape Cod Home with Garden Oasis Inspired by Butchart Gardens Welcome to your year-round retreat, tucked away in a private setting among towering oaks in the heart of New Seabury, Cape Cod. This beautifully maintained 5-bedroom home offers the perfect blend of coastal charm and modern comfort. Step outside into your own slice of paradise—a professionally designed garden inspired by the world-famous Butchart Gardens of Victoria, British Columbia.

Stylish home with beach pass, close to everything

Modern home near Dowses and Craigville beach, Ropes and Loop beach (2.3 miles) with pass included for all ponds, lakes and beaches in Barnstablle. Outdoor shower Beautiful 3 br ranch. Central AC and heating, furniture, beds and kitchen appliances. Private fenced yard with deck, BBQ, fire pit, plenty of seating 2.5 mi to Joshua pond, North Pond- for fishing and Wequaquet Lake for swimming. Main st Hyannis restaurants and clubs, Cape Cod Mall. Fast internet, cable, smart TV.

Opulent Private Waterfront Escape, Family Friendly

Welcome to The Wandery! Escape to the Cape and experience the perfect balance of relaxation and recreation at this spacious and private lakeside retreat! Nestled on a quiet street just minutes from Ocean beaches, shopping, and dining, this beautifully appointed home offers generous indoor and outdoor living areas, ideal for families or groups. Waterfront on Johns Pond Mashpee Commons – 7 min New Seabury Country Club – 7 min Explore Mashpee magic & Learn More Below!

Cape EsCape:2 Rm Private Suite, EZ walk to beaches

Magical ALL year ‘round. location, Location, LOCATION; comfy, contemporary newly renovated (‘21) private bedrm & family rm 0.4mile from neighborhd river-beach, 0.9mi from row of ocean beaches, hiking trails, live theater, everywhere. Separate private entrance. A/C. Queen bed. Outside space with picnic table, chairs, & hammock. Beach chairs provided. W/in 5 min walking distance of bakeries, mini-golf, restaurants, shopping, bike trail, kayaking, & more.

Charming W. Tisbury Studio Guest Cottage

Charming rustic studio guest cottage with a private yard and outdoor shower, a perfect getaway. Walking distance to North Tisbury Farm and Market and State Road Restaurant and short ride to the small town of West Tisbury where you can check out Alley’s general store or get a great sandwich at 7a’s takeout. Ten minutes to Vineyard Haven and centrally located to all island destinations and many of the scenic Vineyard hiking trails.

Beachfront W/ HotTub, Sauna, Pool & Panoramic view

Welcome to the Heart of Somerset! Read our reviews & stay a while! Nestled at the very tip of Somerset on a private dead-end road, this coastal waterfront home is the perfect place for a family retreat, romantic getaway or friends seeking adventure Marvel at the panoramic views and dramatic colors from Sunrise to Sunset. Grab a kayak, or sit back and relax and let the gentle sea breeze wash your worries away!

Waterfront: Private Beach | Kayaks | Pet Friendly

Welcome to your dream getaway! This modern 3-bedroom, 1-bathroom lakehouse offers the perfect blend of relaxation, adventure, and modern elegance. Nestled along the pristine shoreline of Glen Charle Pond, this waterfront escape boasts breathtaking panoramic views, a private dock, and top-tier amenities for an unforgettable stay. Sip your morning coffee as the sun rises, or unwind with a glass of wine at sunset.

Bayberry Cottage- Menemsha Inn & Lucy

Bayberry is a lovely one bedroom and one bath, full kitchen, living room with wood burning fireplace and Roku TV. It includes a private deck with chairs and a screened-in porch with a picnic table. Additional amenities include outside showers, BBQ grill, use of the inn's facilities, and walk-on or car passes to a choice of Chilmark's Private Beaches - Lucy Vincent or Squibnocket during beach pass season.