Holiday rentals in Dukes County

The Blueberry House on Martha’s Vineyard

Welcome to 'The Blueberry House' in Chilmark, up-island in beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. This 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime location off North Road next to North Tabor Farm with quick access to Great Rock Bight preserve, Menemsha Beach and Chilmark Store. Multi-week stays require weekly cleaning $300 each.

Apartment Guest Suite in Modern Barn House

A beautiful guest suite on Martha’s Vineyard with a private entrance on the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this bright and airy 400 space has a sitting area and a full kitchen. Enjoy the outdoor shower and the outdoor sitting area. The location is prime & centrally located, just off historic Music St and a short walk to our small town center, providing many amenities. Ask about our other private guest suite if you are with others.

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.

Sunny Studio Apartment on Martha's Vineyard

Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

Location Location Location! Beach, Bike, Ferry

STEPS to beach, bike path, trails, restaurants, shopping, bus to MV Ferry Gorgeous studio/in law apartment, private entry, own parking + patio Open plan living/sleeping area + en suite bathroom Queen bed + queen sleeper sofa: sleeps max 4 Fresh linens, towels, personal care products, first aid, hairdryer, iron Mini kitchen w fridge, air fryer, microwave, toaster oven, dishwasher, cutlery, crockery, coffee maker Our famous home baked goodies! Coffee/tea/milk/sparkling water provided

Walk to Town, beach and amazing location 113A

Walk to all Oak Bluffs has to offer. 5-10 mins. to harbor, town, beach and dining. Amazing location! This three unit property offers a shared patio and deck space along with all the amenities. It is private and well appointed. 3 flat screen Televisions, wifi, appliances, tile and wood floors, granite counters, outdoor shower, gas grill and best of all it's all brand new. This 2 bedroom unit will provide you with an excellent home base to explore Oak Bluffs and Martha's Vineyard.

Juniper Point Cottage With Ocean View

Charming Cape Cod cottage on a quiet semi-private road with beautiful views of Vineyard Sound. This inviting coastal retreat features 3 bedrooms, 2 private en-suite baths, 1 semi-private en-suite bath, a fully equipped kitchen, gas fireplace, cable TV, WiFi, and air conditioning. Relax on the second-floor deck with water views or enjoy outdoor dining on the patio with the BBQ grill. Conveniently located near the Martha’s Vineyard ferry, bus station, beaches, shops, and town.

Lambert's Cove Oceanview FERRY Tikts See descript

Car FERRY TKTS avail. for purchase for weeks 7/4/26, 7/11/26, and 7/18/26. Salt box home set in the forested hills above Lambert's Cove. Short walk / drive to town beach. Perfect for family gatherings, home has 3 bedrooms , loft for virtual work space or reading room, 1.5 baths plus the fully enclosed outdoor shower, fully stocked kitchen, a deck that has seating for relaxing and also an octagonal picnic table, as well as lots of yard space for children or pups to play.

Your Private Garden

**10% discount for 7 night stays - One bedroom 2nd floor apartment in my owner-occupied home- perfect for a couple - with a spacious eat-in kitchen, shower bathroom, generous living room and separate bedroom. Bright and airy-in a prime location-1/2 block from Main Street, a block from Falmouth Harbor, an easy walk to the beach...with off-street parking. Relax in the secluded area -your Private Garden. Longer bookings eligible for a discount. No smoking please, and no pets.

The Boat House

Located on majestic East Chop and only a mile and a half from both Vineyard Haven and Oak Bluffs, this rustic ocean front cottage offers a unique Martha's Vineyard experience. Whether you relax on the the private beach and watch majestic sunsets, stroll up to East Chop Lighthouse, or head only a little over a mile to vibrant Oak Bluffs harbor, you are sure to have a memorable trip. This is the perfect perfect haven from which to explore Martha's Vineyard.

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!

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.