Vacation rentals with a hot tub in Tisbury

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.

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

This home was custom built in 2022, and is designed to provide comfort, luxury and loads of charm for the discerning vacationer. New construction with a nod to the Nantucket Sea Captain's houses of yesteryear. Professionally decorated and landscaped, offering every amenity you could possibly desire; from an in-ground, heated, saltwater pool (with electric cover), hot tub, outdoor shower, fire-pit, and even a cabana with a sink, refrigerator, and smart TV. Just a 3 min walk to private beach.

Falmouth/Woods Hole Carriage House Roost

Welcome to our Cozy Carriage House Apartment located only a few 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

Snug Harbor - West Falmouth, Cape Cod.

Six bedrooms, four and a half baths, central a/c, just steps from Snug Harbor Enjoy five-star luxury and stunning panoramic views from this shingle style designer home. This home is just a step or two from the harbor's edge, you'll have your own private seaside get-a-way to enjoy. Take a day trip to one of the Islands, Nantucket and Martha's Vineyard, or relax and enjoy the salty breeze from one of the home's many decks or hot tub. You will fall in love this award-winning home.

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.

1BR w/ Fireplace & Beach Access | Pool + Hot Tub

Stay in a cozy 1-bedroom condo at Beachside Village Resort in Falmouth, MA. Enjoy a Queen bed, sleeper sofa, fireplace, and outdoor seating with ocean views. This charming retreat sleeps up to 4 guests and offers 2 full bathrooms, a kitchenette, air conditioning, and beach access. Perfect for couples or families seeking a relaxed Cape Cod experience near historic attractions and local seafood restaurants.

Hideout at Water's Edge, 131 North Shore Blvd, #4

Located in a private beach association & 50ft from a private beach, this 1940’s cottage is surrounded by mature landscaping creating a serene & secluded beach experience. The living room sliding doors look directly onto a beach path, & the North deck offers the best view for sunrises & sunsets. 2 bedrooms, 1 bathroom, & loft space - this cottage is perfect for a relaxing beach trip.

Oak bluffs cottage Perfect place to honeymoon!

Cottage in a quiet part of Oak bluffs. 1/2 Mile from beaches, stores and restaurants. Close to bus lines.Our 2025 calendar now open If you’d like to book! We book up early so please Contact us early for your reservation. Fully heated And air conditioned.