- USA
- Massachusetts
- Dukes County
- Rentals by Owner
Discover Your Ideal Dukes County, Massachusetts rental by owner for a seamless and dependable stay
Discover Your Perfect Dukes County Rentals by Owner
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                                            Rentals by Owner
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                                            Luxury Vacation Rentals
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Dukes County Rentals by Owner
- Air Conditioner
- Parking
- Pool
- Parking
- View
- Ocean View
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- View
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- View
- Ocean View
- Air Conditioner
- Parking
- TV
- Pet Friendly
- Wheelchair Accessible
- Balcony/Terrace
- Security/Safety
- Bedding/Linens
- Wellness Facilities
- Air Conditioner
- Pet Friendly
- Wheelchair Accessible
- Air Conditioner
- Pet Friendly
- TV
Why Choose Rent By Owner for your Dukes County vacation rental?
What makes our Rentals by Owner special?
Best Times to Visit Dukes County
When should you plan your Rentals by Owner stay?
Choosing the ideal time to vacation here can enhance your experience, allowing you to enjoy the region's unique charm at its best while making the most of your rental by owner in Dukes County, Massachusetts.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer daylight hours, making it ideal for outdoor activities and relaxing by the coast in this popular destination.
Fall (September to October)
Early fall offers pleasant temperatures and vibrant foliage, providing a picturesque setting for a memorable visit to the region's charming surroundings.
Off-Season Highlights
Spring (April to May)
In spring, the area starts to bloom with milder weather, making it suitable for quieter explorations and enjoying the natural beauty without the crowds.
Winter (December to February)
During the winter months, the region experiences cooler temperatures, offering a peaceful retreat and opportunities for cozy accommodations away from peak times.
Weekly Weather Forecast for Dukes County
How to Book Your Dukes County vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Dukes County
Common Rentals by Owner Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for savoring local flavors while taking in the fresh air.
- Relax on spacious decks or patios that offer stunning views of the surrounding landscape.
- Make use of private gardens or yards to unwind, play, or host gatherings during your stay.
- Take advantage of outdoor seating or lounge areas designed for relaxation in a peaceful setting.
- Utilize barbecue grills to cook meals outdoors and enhance your vacation experience here.
- Explore nearby outdoor recreational spaces with amenities like picnic tables and open fields.
- Benefit from easy access to outdoor entertainment features such as fire pits or seating areas for evenings under the stars.
Top Attractions Around Dukes County
What attractions are nearby?
Within this charming region, you can enjoy a variety of outdoor activities such as scenic beaches, tranquil parks, and boat outings, making it an ideal destination for relaxing and exploring while staying in your Rent By Owner rental.
 
                
            Family Activities
- Bike the Bike Trails: Explore scenic biking routes that wind through the region, providing an active way for families to enjoy the natural beauty of the area.
- Visit Local Beaches: Spend a relaxing day at the pristine beaches nearby, perfect for swimming, building sandcastles, and soaking up the sun with loved ones.
- Discover Nature at Regional Parks: Enjoy family-friendly activities such as hiking, picnicking, and wildlife watching at parks renowned for their lush landscapes in this destination.
- Participate in Community Events: Engage with seasonal festivals and outdoor events held throughout the region, offering fun-filled entertainment suitable for all ages.
Adult Activities
- Harbor Cruises: Experience the stunning coastline and scenic views through a harbor cruise that showcases the natural beauty of this region.
- Farmers Markets: Explore local farmers markets to enjoy fresh produce and artisanal goods, immersing yourself in the area's vibrant community spirit.
- Bicycle Tours: Discover charming neighborhoods and scenic nature trails on guided or self-led bicycle tours that highlight the region's outdoor appeal.
- Historical Sightseeing: Visit historical sites and museums to deepen your understanding of the area's rich heritage and cultural significance.
Other Places to Stay in Dukes County, MA
Dukes County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities Ahead: Familiarize yourself with the local events and attractions to maximize your leisure time while staying in this charming region.
- Select a Strategic Location: Choose a rental close to key sights and amenities to experience the best of the area without long commutes.
- Embrace Local Cuisine: Take advantage of nearby dining options or prepare meals in your rental to enjoy authentic regional flavors during your visit.
- Communicate Clearly with Hosts: Reach out to your property owner for insider tips and ensure a smooth, enjoyable stay in this welcoming destination.
Transportation Options
- Ferry Services: You can comfortably explore nearby islands and enjoy scenic routes with reliable ferry services operating throughout the region.
- Public Transportation: Buses and shuttles provide convenient access to key destinations within Dukes County, making it easy to get around without a car.
- Rental Cars: Renting a vehicle offers flexibility for your adventures across this picturesque area, with numerous rental agencies available locally.
- Taxi and Rideshare: Taxis and rideshare options like Uber and Lyft ensure quick, hassle-free transportation when you need to navigate this charming destination.
Local Customs Options
- Respect for Local Fisheries: You’ll find that supporting sustainable fishing practices is a valued custom here, reflecting the region’s deep connection to maritime traditions.
- Celebration of Maritime Heritage: Participating in local festivals and honoring the area's historic seafaring customs will enhance your understanding of this destination’s rich nautical history.
- Environmental Conservation Efforts: Visitors are encouraged to engage in eco-friendly activities and respect protected natural areas, which are central to preserving the region’s pristine landscapes.
- Community Gatherings and Events: Embracing local social traditions through community events allows you to experience the welcoming spirit that characterizes this part of Massachusetts.
Frequently Asked Questions About Dukes County Rentals by Owner
1. What are the top vacation rentals in Dukes County?
There are a lot of options in Dukes County. If you plan on staying in the Dukes County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Dukes County:
- In-Town Certified National Historic Oak Bluffs Property -
- New construction Edgartown home with AC, new furnishings, o/d shower, bike path.
- On HGTV! New w/Hot Tub, Bocce Court, AC, WALK to Town & Beach!
- Marthas Vineyard Edgartown Cottage - Easy walk to village, outdoor shower, linen
- Quaint Martha's Vineyard Guest Cottage -Edgartown-walk to restaurants and shops
- Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
- Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path
- Multiple Ensuites, Central Air, Perfect Location
- Close to Lambert's Cove Beach. Pastoral setting. Elegant farmhouse & guest house
- Charming, Clean And Well Maintained Home Walking Distance To Town And Beach
2. How many Rentbyowner vacation rentals are available in Dukes County?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 1489 in the Dukes County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Dukes County.
3. What is the cancellation policy for a rental by owner in Dukes County, Massachusetts?
4. How do I communicate with the property owner before booking in Dukes County, Massachusetts?
5. Are there any additional fees for rentals by owner in this area?
6. What amenities are commonly included in rentals by owner here?
7. How do I confirm my booking in Dukes County, Massachusetts?
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