Discover Your Perfect Dukes County Vacation Homes

Best Vacation Homes in Dukes County

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Dukes County Luxury Rentals

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Find More Dukes County Villas, Resorts, & Rentals on BedroomVillas

Dukes County Pet Friendly Vacation Rentals

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10.0 (1 Review)
House
Hillside Oak
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace
View Availability
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9.0 (1 Review)
House
Brewster House
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace
View Availability
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Why Choose Rent By Owner for your Dukes County Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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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 Vacation Rentals stay?

Choosing the ideal time to visit here can significantly enhance your experience, as this destination offers seasonal charms that cater to various interests throughout the year.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this destination experiences its peak visitor influx, making it an ideal time for beach lovers and outdoor enthusiasts to enjoy the region’s natural beauty.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
autumn
Fall (September to November)

Autumn showcases vibrant foliage and mild weather, attracting travelers seeking scenic views and a peaceful atmosphere in this popular region.

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

Off-Season Highlights

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Winter (December to February)

During winter, fewer visitors arrive, providing a quiet retreat with cooler temperatures that appeal to those seeking solitude and cozy surroundings in the area.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 35°F
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Early Spring (March to May)

In early spring, the region sees a slowdown in tourist activity as nature begins to awaken, offering a tranquil experience before the busy summer season begins.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 45°F

Weekly Weather Forecast for Dukes County

How to Book Your Dukes County Vacation Rental Home

What's our booking process?

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

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

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 Vacation Rentals in Dukes County Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 seafood and fresh produce.
  • Relax by a private or shared swimming pool to cool off during warm summer days.
  • Take advantage of spacious decks or patios ideal for soaking up the regional sun.
  • Explore beautifully landscaped gardens or yards that showcase the area's natural beauty.
  • Make use of outdoor grills for convenient barbecues with family and friends.
  • Utilize shared or private outdoor seating areas to unwind after days spent exploring the region.
  • Benefit from nearby access to scenic walking or biking paths that highlight the area’s natural charm.

Top Attractions Around Dukes County

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities such as exploring scenic beaches, engaging in water sports, or visiting local parks that offer a peaceful retreat just moments from your vacation rental.

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Family Activities

  • Beach Day at South Beach: Enjoy a relaxing day building sandcastles and splashing in the gentle waves along this popular stretch of shoreline here in Dukes County.
  • Visit the Martha's Vineyard Museum: Discover the local history and culture through engaging exhibits that educate and entertain family members of all ages in this region.
  • Explore the Felix Neck Wildlife Sanctuary: Embark on nature walks and explore wildlife habitats, offering an educational outdoor experience for the whole family on the island.
  • Take a Whale Watching Tour: Experience the thrill of spotting whales and marine life in the surrounding waters, creating unforgettable memories here in Dukes County.
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Adult Activities

  • Bird Watching Tours: Explore the diverse avian species that thrive in the region, making it a perfect activity to enjoy nature and observe wildlife here.
  • Beachcombing and Coastal Walks: Stroll along picturesque beaches and discover local shells and marine life, immersing yourself in the tranquil coastal scenery of this destination.
  • Historical Site Visits: Delve into the area's rich history by touring renowned sites that showcase its cultural heritage and storied past.
  • Sailing and Boating Excursions: Experience the region’s waters firsthand with sailing trips or boat rentals, offering breathtaking views and a touch of adventure here.

Other Places to Stay in Dukes County, MA

Martha's Vineyard
Martha's Vineyard Vacation Rentals
Edgartown
Edgartown Vacation Rentals
Oak Bluffs
Oak Bluffs Vacation Rentals
Vineyard Haven
Vineyard Haven Vacation Rentals
Tisbury
Tisbury Vacation Rentals
Katama
Katama Vacation Rentals
Chilmark
Chilmark Vacation Rentals
West Tisbury
West Tisbury Vacation Rentals
East Chop
East Chop Vacation Rentals
Lagoon Heights
Lagoon Heights Vacation Rentals
Lake Tashmoo
Lake Tashmoo Vacation Rentals
Aquinnah
Aquinnah Vacation Rentals
More Places to Stay Near Dukes County

Dukes County Travel Tips

How Can You Make the Most of Your Stay?

  • Plan ahead for the local attractions: Research popular sights and activities in the region to maximize your experience during your stay.
  • Choose accommodations with proximity to key destinations: Opt for vacation rentals that are conveniently located near the area's main points of interest.
  • Embrace the local culture and cuisine: Take time to explore regional restaurants and cultural events to fully immerse yourself in this destination.
  • Utilize local transportation options: Familiarize yourself with available transit methods to easily navigate the area and make the most of your trip.

Transportation Options

  • Dukes County Ferry Service: This popular transportation option offers scenic and reliable ferry rides to various islands, providing a unique way to explore the region from your vacation rental.
  • Island Water Taxi: For quick access to nearby islands and beaches, water taxis offer flexible and convenient services directly from the mainland here.
  • Regional Bus Services: Local buses connect key areas within Dukes County, making it easy to navigate between towns and popular destinations while staying close to your rental property.
  • Rental Cars: Renting a car gives you the freedom to explore the area's scenic landscapes and attractions at your own pace, enhancing your stay in this charming destination.

Local Customs Options

  • Harboring a love for the sea: In this coastal region, locals strongly value maritime traditions, reflecting a deep connection to fishing and boating that you can observe during your stay.
  • Celebrating local festivals: The area hosts annual events that showcase its rich history and community spirit, offering you an authentic glimpse into local customs.
  • Embracing sustainable fishing practices: Many residents prioritize environmentally conscious approaches to fishing, emphasizing conservation efforts that you might hear about during your visit.
  • Respecting quiet coastal surroundings: Visitors are encouraged to maintain tranquility and preserve the natural beauty of the region's beaches and residential neighborhoods.

Frequently Asked Questions About Dukes County?

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 have private pools in Dukes County?

There are 115 vacation rentals with private pools near Dukes County. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Dukes County are best for families?

If you are looking for a family-friendly vacation home in Dukes County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Dukes County:

4. How many Rentbyowner vacation rentals are available in Dukes County?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 1785 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. 

5. What is the cancellation policy for vacation rentals in Dukes County, Massachusetts?

Cancellation policies vary depending on the specific property you choose. To understand the terms related to refunds and cancellations, please review the listing details or contact the property owner directly.

6. How do I ensure my reservation is secure when booking a rental here?

Reservations are secured through verified listings with trusted payment options. For added peace of mind, read the property's reviews and confirm the booking details before finalizing your reservation.

7. Are there any additional fees I should be aware of when booking a vacation rental in this destination?

Additional fees such as cleaning, service charges, or security deposits may apply. These will be clearly outlined in the listing, so reviewing the full cost breakdown before booking is recommended.

8. Can I modify or cancel my booking if my travel plans change?

Modification and cancellation policies depend on the individual property’s rules. Contact the host directly or check the listing's terms to understand your options should your plans change.

9. What amenities are typically included in vacation rentals around Dukes County, Massachusetts?

Amenities can vary, but most rentals offer essentials like Wi-Fi, kitchen facilities, and linens. For specific amenities, please refer to the property listing or reach out to the owner for detailed information.

Dukes County Top Rated Vacation Rentals

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