Dukes County, MA Rentals by Owner

Dukes County Rentals by Owner

4 bedroom home family friendly in desirable area

New

House

4 bedroom home family friendly in desirable area

10.0

Exceptional

(42 Reviews)

4 Bedrooms 2 Baths 10 Guests 2500 ft²

US $609/Night 7 Nights - US $4,261

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Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

House

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

10.0

Exceptional

(4 Reviews)

2 Bedrooms 2 Baths 4 Guests 1097.92 ft²

US $239/Night 7 Nights - US $1,673

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Highly Rated

House

The Lightkeepers Inn

9.4

Exceptional

(211 Reviews)

1 Bedroom 1 Bath

US $905/Night 7 Nights - US $6,335

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Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom

New

House

Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom

10.0

Exceptional

(33 Reviews)

4 Bedrooms 1 Bath 6 Guests 1800 ft²

US $321/Night 7 Nights - US $2,247

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House

Modern Family Home Walkable to Town

10.0

Exceptional

(2 Reviews)

4 Bedrooms 3 Baths 8 Guests 10763.91 ft²

US $760/Night 7 Nights - US $5,320

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Charming West Chop Retreat on Private, Tree-Lined Lot

Price Dropped

House

Charming West Chop Retreat on Private, Tree-Lined Lot

10.0

Exceptional

(27 Reviews)

4 Bedrooms 2 Baths 8 Guests 2200 ft²

US $734/Night 7 Nights - US $5,135

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House

Hillside Oak

10.0

Exceptional

(1 Review)

4 Bedrooms 4 Baths 8 Guests 3336.81 ft²

US $914/Night 7 Nights - US $6,398

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House

Edgartown/Katama Newly Renovated Vineyard Escape

10.0

Exceptional

(26 Reviews)

3 Bedrooms 2 Baths 8 Guests

US $702/Night 7 Nights - US $4,913

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House

Summer Daze

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 6 Guests 1388.54 ft²

US $873/Night 7 Nights - US $6,111

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Modern Coastal Katama Retreat - 4th Season of 5 Star Summers

Top 10% in Katama

House

Modern Coastal Katama Retreat - 4th Season of 5 Star Summers

10.0

Exceptional

(21 Reviews)

3 Bedrooms 3 Baths 7 Guests

US $1,445/Night 7 Nights - US $10,114

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House

Easy Access to Beaches: Vineyard Haven House

10.0

Exceptional

(1 Review)

3 Bedrooms 1 Bath 6 Guests 2787.85 ft²

US $491/Night 7 Nights - US $3,437

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Humble Abode/Charming Cottage Near Long point Beach

New

House

Humble Abode/Charming Cottage Near Long point Beach

10.0

Exceptional

(20 Reviews)

3 Bedrooms 1 Bath 6 Guests 1700 ft²

US $934/Night 7 Nights - US $6,536

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More Top-Rated Rentals by Owner in Dukes County Area

Why Choose Rent By Owner for your Dukes County vacation rental?

What makes our Rentals by Owner special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

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.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F

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.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 55°F

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.

Average Temperature Daytime: 55°F to 65°F - Nighttime: 45°F to 50°F

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.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 25°F to 30°F

Weekly Weather Forecast for Dukes County

How to Book Your Dukes County vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Dukes County

More Top-Rated Rentals by Owner in Dukes County Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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.

Dukes County Rentals by Owner Frequently Asked Questions

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:

2. How many Vacation Rentals are available in Dukes County?

Currently, the total number of properties listed by RBO in 2026 is over 1645 in the Dukes County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Dukes County. 

3. What is the cancellation policy for a rental by owner in Dukes County, Massachusetts?

The cancellation policy varies depending on the individual listing. You should review the specific terms outlined in the property's description or contact the owner directly to understand the refund options and any associated fees.

4. How do I communicate with the property owner before booking in Dukes County, Massachusetts?

You can reach out to the owner through the messaging platform provided on the booking site. This allows you to ask questions, clarify details, and ensure the rental meets your needs before finalizing your reservation.

5. Are there any additional fees for rentals by owner in this area?

Additional fees such as cleaning, service charges, or security deposits are typically specified in the listing. It's advisable to read the full listing details or contact the owner directly to understand all costs involved.

6. What amenities are commonly included in rentals by owner here?

Most properties offer essential amenities like Wi-Fi, parking, and kitchen facilities. However, specific features vary, so reviewing the listing carefully or communicating with the owner ensures your needs are met during your stay.

7. How do I confirm my booking in Dukes County, Massachusetts?

Once you select your preferred rental, you'll typically complete a reservation request that the owner must approve. After confirmation, you'll receive detailed check-in instructions and further information to prepare for your visit.