Guest house holiday rentals in Dukes County

THE BIG CHILL ~ ONE MILE TO EDGARTOWN CENTER

The Big Chill is close to the buses, grocery stores, fish markets, Morning Glory Farm, the beautiful beaches and the center of Edgartown. You’ll love it.. its cozy, has A/C, you'll love the high ceilings on the second floor and the location! The BIG CHILL has a full bath indoors and a fully enclosed outdoor shower steps from the door. Great for couples, solo adventurers, and business travelers….a bike ride to town. If you need a bigger house, check out Sandy Feet Retreat for 5-10 guests.

Vineyard Meadow Artist Studio

This lovely artist's studio is just steps from miles of trails. Walk to the beach or meander through the woods of Long Point Wildlife Refuge, experiencing the serenity of this still untouched corner of Martha's Vineyard. This studio includes a bathroom with a shower, a washer/dryer and a kitchenette. It is the perfect spot for a lone artist, a couple or a family to enjoy Martha's Vineyard any time of year. This property shares the driveway and parking with Vineyard Meadows Writer's Cottage.

Wedding RetreatTrails Golfing Beaches Private Gem

✨ LOCATION, LOCATION✨ ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood 🌳 Hidden trails—Great for exploring 🏡 Perfectly Getaway, ✅ Easy access to all towns, Hassle-free stay. 🚗 Just 8 minutes to local markets, and top-rated restaurants. 🚴‍♂️ A scenic 13-minute bike ride takes you to the charming Edgartown Village or Katama South Beach—perfect for breathtaking sunsets! Convenience, comfort, and nature at your doorstep.

Beautiful Guest House in Chilmark

This newly renovated guest house is located in a quiet and very private setting in Chilmark. The guest house is located above the garage adjacent to the main house with a private entrance. It has a queen size bed with two oversized chairs. There is a full bathroom in addition to a private outdoor shower. A small kitchen features butcher block countertops, a stainless steel sink, refrigerator and electric stove. Central air conditioning + heat make it the perfect getaway for all seasons.

Martha’s Vineyard Cottage - A Glamping Experience!

This is your vineyard home, where you can walk or ride a bike less than a mile to the beach or two into town. Get the glamping experience with kitchenette, A/C, an outdoor shower, a composting toilet, a queen bed in the loft and futon couch that can sleep two more in the living room. Enjoy outdoor games, outdoor seating, a Weber grill for bbq, tv, WiFi, cozy indoor space and more, right on the bike path with a bus stop for easy accessibility or free car parking. Whatever you want!

King bed, Water Views,AC,Near Bike Path- Bus stop

Have your morning coffee looking out at the sunrise and sailboats from your living room or bedroom windows. This modern studio feels secluded while only a mile and a half from Main Street Vineyard Haven, four miles from Oak Bluffs, and eight miles to Edgartown. This is the perfect place to unplug but does come equipped with everything you need, including wifi, smart tv, fully equipped kitchen, beach towels, linens, and bath towels for your stay.

Country cottage walk to Alley's General Store

This sunlit summery cottage is in a very quiet, private and pastoral setting, situated 100 feet from the small Tiasquam River, with many birds chirping in the abundant vegetation and trees nearby. Because of the river's proximity, the cottage has a Composting Toilet. My wife and I live on the property uphill from the cottage. The property is in the countryside but a 5 minute walk to the local town center.

Sweet Vineyard Haven Cottage

Booking for 2025 season; Spring, Summer and Fall is OPEN. Walk to Main Street Vineyard Haven and ferry from this classic, comfy cottage with great screened porch and well equipped kitchen. No car, no problem. Upgraded A/C, premium cable and a new outdoor shower!

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.