Holiday rentals with a hot tub in Dukes County

Cozy Autumn Cottage | Hot Tub + Pet Friendly

Welcome to your cozy Cape cottage! The perfect autumn escape. Enjoy the steamy hot tub, sip cider by the fire pit, or breathe the crisp ocean air on a walk. Our space offers comfort, warmth, and seasonal charm. This cottage blends indoor comfort with outdoor beauty – ideal for long weekends, wedding guests, romantic getaways, and marathon runners. Walk to local restaurants, the Martha’s Vineyard ferry, and scenic paved paths. Fall brings fewer crowds, colorful foliage, and a beautiful coastline.

Top-Rated Island Retreat: Hot Tub, Lamberts Cove!

Welcome to Oakhaven - your beautiful Vineyard retreat with privacy, parking & outdoor living. • 3 bedrooms (1 king, 2 full, 1 twin) • 2 baths + outdoor shower • Queen sleeper in living room (House Sleeps 7 - MAX) Enjoy the patio, hot tub (mid May–Sept), screened gazebo w/ fan/light, and al fresco dining by the outdoor fireplace. Linens, bath towels & beach gear provided. NOTE: August reservations require a min. 5-night stay, and bookings must run consecutively without gaps in the calendar.

Modern Family-home,POOL with lots of outdoor space

Staying in this spacious Martha's Vineyard home is extraordinary. With its modern structure, in both the main and guest house, not to mention the patios, and decks full of greenery and flowers. Enjoy the houses perks, check out the brand new hot tub, fire pit and outdoor grill! You'll love making memories with family and friends with all our outdoor accessories, like the showers and dining area (right next to the grill). And if your feeling extra active, enjoy a workout in the guest house gym.

2 BR-Private guest house with Hot Tub and Fire Pit

Welcome to our charming 2-bedroom private guest house, nestled in a peaceful Chilmark neighborhood. Enjoy the spacious outdoor area, perfect for gatherings, featuring an 8-person dining set, a wood-burning fire pit, a BBQ grill, a 6-person hot tub, and a seasonal outdoor shower. Our location offers easy access to local attractions: just a 4-minute drive to Alleys General Store, West Tisbury Center, and the library, and only 5 minutes to the stunning Lucy Vincent Beach and Chilmark town center.

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Vineyard Meadow Writer's Cottage

This lovely retreat is just steps from miles of trails. Walk to the beach or meander through woods of Long Point Wildlife Refuge, experiencing the serenity of this untouched corner of Martha's Vineyard. After a day of enjoying the outdoors, come home to the light and airy writer's retreat. With a hot tub (open May 1 - Jan. 2), an outdoor shower and wonderful kitchen, this is the perfect location for a get-away with family and friends or for a creative retreat with your fellow artists.

On HGTV! Gorgeous, AC, Hot Tub, WALK Town & Beach

Enjoy this large, open, airy and sun drenched custom home built in 2000 in the desirable Katama neighborhood on a half-acre with southern exposure and central A/C. Soak up the sun on the large grassy lawn or brick patio, curl up with iced tea and a book on the 3-season screen porch, grill burgers on the patio's gas grill, or enjoy a beer in the hot tub. You're a couple minutes away or a short bike ride to South Beach, Right Fork Diner, Edgartown main street, and Morning Glory Farm.

Falmouth/Woods Hole Charming Cottage By the Sea

Welcome to our Cottage By The Sea Rental located only minutes from the quaint village of Woods Hole, Falmouth and the Martha's Vineyard Ferry. We are located in the perfect setting to relax and enjoy all the area has to offer. Come enjoy The Shining Sea Bike path which is 10.7 miles , Sandy beaches, lively restaurants & local music scene, shopping on historic Main Street, Farmers Markets & more. Your sure to fall in Love with " Ole Cape Cod " when you visit our home and area

Valentine's Retreat Hot Tub Fire Pit Trails Beach

LOCATION LOCATION ✅ Rated Top 5% of Homes ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood ✅ HotTub, Fire Pit, Trails at your door step, perfect for peaceful strolls or energetic hikes through lush landscapes. AND Flexibility, with Every detail curated for comfort and style, you'll feel at home the moment you step inside. Located with the island's natural beauty around you, unwind and reconnect with nature.

** Vineyard Vacation Retreat ** with HOT TUB

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home. Updated 7/25/2025 we do not have any more firewood on the property.

Stunning 4/2.5 Water View, Hot Tub, Dogs ok

Custom-build home with beautiful water views of Lagoon Pond. Surrounded by Land Bank and Sheriff's Meadow, this property is extremely private and offers easy access to miles of hiking trails and pristine waters. Enter the home from the covered porch; the main level features an open floor plan, high ceilings in the living areas - open to the dining room and kitchen, where large windows frame the Lagoon. Sleeps up to 8. Outdoor shower! Wifi speed 430 MBPS download speed

Waterside Guest House

Clean, oceanfront, cozy guesthouse located steps from ocean and beach. Sleeps 2-4. Panoramic views of Martha's Vineyard & Vineyard Sound. Tennis Court, Wifi, Cable, & your own private heated outdoor whirlpool are available year round; swimming pool seasonal. Pricing is wide ranging - from $99/night in winter to $499/night in mid-summer.