Vacation rentals with a kayak in Chilmark

Fair Heaven, your West Island beachfront home

Escape to the beach for a private family reunion or a romantic getaway! Fair Heaven will enchant and accommodate you in luxury. Enjoy the sounds of gentle waves lapping at the private beach and wake up to a day where you may swim off the beach, bike over to the bike trail, or take kayaks out on the warm waters of Buzzard’s Bay. Water shoes are advised on our beach (rocks and shells). A sandy beach is just down the road - permit will be provided. (Certified Massachusetts lodger #C0020560940)

Private Waterfront Home on Picturesque Pond

Welcome to this bright and airy waterfront home on beautiful Mares Pond. This tranquil property is the perfect place to spend some time away in a peaceful setting, and is set up wonderfully for multiple families. The house is perfectly located to enjoy all that Falmouth has to offer. Just 10 minutes to Falmouth ocean beaches, Falmouth Village shopping and restaurants. Drive or take the trolley to Woods Hole in less than 20 minutes, or hop on the ferry to Martha's Vineyard just down the road.

Vineyard Haven Walk to Ferry

I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

Quiet & Serene in Aquinnah

Fall asleep to the sounds of the waves. Unique 1000 sqft. 1st floor suite, surrounded by conservation lands and adjacent to the new 320 acre Squibnocket Pond Reservation. The suite consists of 2 elegantly furnished bedrooms and a large marble bathroom. Three sets of French doors open onto an expansive terrace with gardens. Larger bedroom has a beach stone fireplace with a wood stove. 12 minute walk to private beach. Owner occupied on 2nd floor. Charming and serene. Pet Friendly

Waterview, Private, Walk to Beach, Mile to Town

Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Ask the host about ferry reservations if they appear to be sold out!

Cozy Cottage on a Private Pond

This cozy cottage is located on a private 42 acre, spring fed, crystal clear private pond. Enjoy kayaking, swimming or fishing from the dock or just relax on the deck overlooking the pond. Sleeps 5 in 2 bedrooms and trundle bed in the 4 season room. There is good fishing and canal cruises, cafes and restaurants close by and a summer concert series in park. Many of our guests with children have visited Edaville Railroad and "Thomasville" It is about 15 miles from the cottage

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

The Blue Lagoon, Oak Bluffs

Come enjoy this beautifully designed, brand new home. With 3 bedrooms and 3 full bathrooms you will have all the space you need. An outdoor patio with gas grill is the perfect spot to relax after a day at the beach. Just a few steps away is the lagoon where you can paddle board, kayak, dig clams, or just take in the amazing sunsets! Summer rentals are Saturday to Saturday. Please send a message if you have any questions.

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!

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.

Sunset Cove Beach

This ocean view cottage is perfect for you and your family to relax, unwind and adore the wonderful scenery it has to offer. This charming cottage is on a quiet dead-end street, suitable for a small family or a couple, seeking to appreciate the neighborhood and beaches without the hassle of cape traffic. Come and enjoy the warm water, beautiful sunrises, breathtaking sunsets, and much more.

“Cozy Cottage” on Great Bay

Our Cozy waterfront cottage is located 120ft from great bay. Our closest beach is 2.5 miles and we are 4 miles from the center of town. Equipped with gas heat and Central A/C. We also have a gas fired fireplace to keep you cozy. Outside shower for days at the beach. We have one single kayak, two double Kayaks, a rowboat and a canoe for a scenic view of Great Bay. Quiet spot.