Best Vacation Homes in Dukes County
House
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
Fireplace/Heating
Ocean View
Balcony/Terrace
View
R12,574/Night
7 Nights - R88,024
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1097.92 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- View
R3,913/Night
7 Nights - R27,393
Bed & Breakfast
9.8(245 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
Breakfast
Kitchen
Air Conditioner
R4,362/Night
7 Nights - R30,537
New
House
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
R83,521/Night
7 Nights - R584,649
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
10763.91 ft²
- Fireplace/Heating
- View
- Air Conditioner
- Internet
R12,444/Night
7 Nights - R87,107
New
House
3 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R59,836/Night
7 Nights - R418,851
New
House
5 Bedrooms
5 Baths
12 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R45,910/Night
7 Nights - R321,379
New
House
5 Bedrooms
4 Baths
12 Guests
2500 ft²
Private Pool- Oceanfront
Hot Tub- Fireplace/Heating
R42,289/Night
7 Nights - R296,033
Dukes County Luxury Rentals
House
9.8(17 Reviews)
6 Bedrooms
5 Baths
16 Guests
7000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
Unlock the Best Price
House
10.0(3 Reviews)
6 Bedrooms
4 Baths
15 Guests
5500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
Pool
R146,836/Night
7 Nights - R1,027,847
New
House
6 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R128,460/Night
7 Nights - R899,217
New
House
5 Bedrooms
6 Baths
10 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R114,997/Night
7 Nights - R804,988
New
House
4 Bedrooms
4 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R110,606/Night
7 Nights - R774,238
House
10.0(70 Reviews)
12 Bedrooms
7 Baths
28 Guests
5000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R106,466/Night
7 Nights - R745,257
House
9.6(4 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R102,550/Night
7 Nights - R717,848
House
4 Bedrooms
3 Baths
8 Guests
- Hot Tub
Spa- Fireplace/Heating
- Ocean View
R92,753/Night
7 Nights - R649,275
Dukes County Pet Friendly Vacation Rentals
New
House
4 Bedrooms
5 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R39,698/Night
7 Nights - R277,891
House
10.0(1 Review)
1 Bedroom
4 Baths
8 Guests
3336.81 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Child Friendly
R14,965/Night
7 Nights - R104,758
New
House
5 Bedrooms
3 Baths
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R26,518/Night
7 Nights - R185,627
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1001.04 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
R7,106/Night
7 Nights - R49,743
House
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R20,249/Night
7 Nights - R141,746
New
Cottage
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R10,529/Night
7 Nights - R73,697
Apartment
10.0(155 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R11,827/Night
7 Nights - R82,784
Cottage
10.0(98 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R7,586/Night
7 Nights - R53,099
Dukes County Large Vacation Homes
House
12 Bedrooms
7 Baths
20 Guests
- Fireplace/Heating
- Internet
- Child Friendly
Laundry
R40,707/Night
7 Nights - R284,948
Bed & Breakfast
9.9(61 Reviews)
7 Bedrooms
6 Baths
17 Guests
477.2 ft²
- Balcony/Terrace
- View
Parking- Air Conditioner
R2,964/Night
7 Nights - R20,745
House
10.0(6 Reviews)
6 Bedrooms
3 Baths
16 Guests
3300 ft²
R17,237/Night
7 Nights - R120,656
House
9.8(8 Reviews)
2 Bedrooms
2 Baths
10 Guests
3872 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R11,558/Night
7 Nights - R80,902
House
9.5(4 Reviews)
5 Bedrooms
2 Baths
8 Guests
1797.57 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
R4,470/Night
7 Nights - R31,290
House
10.0(89 Reviews)
5 Bedrooms
4 Baths
10 Guests
3600 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
R19,478/Night
7 Nights - R136,342
House
10.0(81 Reviews)
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R33,574/Night
7 Nights - R235,009
House
10.0(81 Reviews)
4 Bedrooms
2 Baths
11 Guests
2000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R8,617/Night
7 Nights - R60,320
Why Choose Rent By Owner for your Dukes County Vacation Rental Homes?
What makes our Vacation Rentals 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 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 (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
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
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
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
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.
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.
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
Edgartown
Oak Bluffs
Vineyard Haven
Tisbury
Lake Tashmoo
Katama
West Tisbury
Lagoon Heights
Chilmark
East Chop
Aquinnah
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:
- In-Town Certified National Historic Oak Bluffs Property -
- Newer construction Edgartown home with AC car ferry tkt avail. 6-27 to 8-22
- 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
- Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path.
- Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path
- Multiple Ensuites, Central Air, Perfect Location
- Charming, Clean And Well Maintained Home Walking Distance To Town And Beach
2. How many vacation rentals have private pools in Dukes County?
There are 120 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 1887 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
House
10.0(104 Reviews)
1 Bedroom
1 Bath
4 Guests
518 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R8,169/Night
7 Nights - R57,193
House
10.0(71 Reviews)
6 Bedrooms
3 Baths
10 Guests
3000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R19,514/Night
7 Nights - R136,604
House
10.0(61 Reviews)
5 Bedrooms
3 Baths
10 Guests
3500 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R19,429/Night
7 Nights - R135,998
House
10.0(61 Reviews)
1 Bedroom
1 Bath
2 Guests
896 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R16,332/Night
7 Nights - R114,320
House
10.0(54 Reviews)
6 Bedrooms
5 Baths
12 Guests
3650 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R48,366/Night
7 Nights - R338,572
House
10.0(39 Reviews)
5 Bedrooms
4 Baths
14 Guests
2727 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R35,711/Night
7 Nights - R249,974
House
10.0(29 Reviews)
7 Bedrooms
5 Baths
16 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R44,809/Night
7 Nights - R313,667
House
10.0(28 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R7,756/Night
7 Nights - R54,295
