Discover Your Perfect Williamsburg Vacation Homes

Best Vacation Homes in Williamsburg

New
24 Guests 8 Bedrooms 8 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
R13,860/Night For 7 Nights R97,017
10.0
Exceptional
(5 Reviews)
382.12 ft² 10 Guests 4 Bedrooms 4 Bathrooms
Family Friendly Bed & Breakfast
  • View
  • Parking
  • Air Conditioner
R3,979/Night For 7 Nights R27,854
9.6
Exceptional
(187 Reviews)
1 Bedroom 1 Bathroom
Couples Retreat Bed & Breakfast
  • Fireplace/Heating
  • Balcony/Terrace
  • Breakfast
R5,006/Night For 7 Nights R35,045
New
1015 ft² 24 Guests 8 Bedrooms 8 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
R11,249/Night For 7 Nights R78,745
10.0
Exceptional
(2 Reviews)
1453.13 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Free Cancellation House
  • Fireplace/Heating
  • Parking
  • Internet
R7,163/Night For 7 Nights R50,134
New
1531 ft² 20 Guests 6 Bedrooms 6 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
R7,157/Night For 7 Nights R50,100
New
1530 ft² 10 Guests 3 Bedrooms 3 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Spa
  • Fireplace/Heating
R4,513/Night For 7 Nights R31,592
4.8
Average
(3 Reviews)
2 Bathrooms
Family Friendly Hotel
  • Hot Tub
  • Fireplace/Heating
  • Pool
R3,074/Night For 7 Nights R21,522

Williamsburg Luxury Rentals

New
8 Guests 3 Bedrooms 3 Bathrooms
Pet Friendly Cottage
  • Pool
  • Pet Friendly
  • Air Conditioner
R27,867/Night For 7 Nights R195,079
10.0
Exceptional
(46 Reviews)
8000 ft² 12 Guests 5 Bedrooms 5 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Breakfast
R24,991/Night For 7 Nights R174,938
10.0
Exceptional
(36 Reviews)
16 Guests 6 Bedrooms 6 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Breakfast
R24,142/Night For 7 Nights R168,993
10.0
Exceptional
(31 Reviews)
16 Guests 5 Bedrooms 7 Bathrooms
Family Friendly Bed & Breakfast
  • Fireplace/Heating
  • Balcony/Terrace
  • Breakfast
R20,780/Night For 7 Nights R145,467
New
2 Guests 1 Bedroom 1 Bathroom
Family Friendly Villa
  • Hot Tub
  • Spa
  • Fireplace/Heating
R19,502/Night For 7 Nights R136,508
New
4 Guests 1 Bedroom 1 Bathroom
Family Friendly Villa
  • Hot Tub
  • Spa
  • Fireplace/Heating
R19,502/Night For 7 Nights R136,508
New
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Villa
  • Hot Tub
  • Spa
  • Fireplace/Heating
R19,502/Night For 7 Nights R136,508
8.8
Fabulous
(5 Reviews)
16 Guests 4 Bedrooms 4 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Air Conditioner
R19,361/Night For 7 Nights R135,531

Williamsburg Pet Friendly Vacation Rentals

9.8
Exceptional
(99 Reviews)
1100 ft² 4 Guests 2 Bedrooms 1 Bathroom
Ocean View House
  • Fireplace/Heating
  • Ocean View
  • Balcony/Terrace
R3,042/Night For 7 Nights R21,286
10.0
Exceptional
(1 Review)
1194.79 ft² 8 Guests 2 Bedrooms 2 Bathrooms
Free Cancellation House
  • Balcony/Terrace
  • Pet Friendly
  • Parking
R3,486/Night For 7 Nights R24,402
9.0
Exceptional
(78 Reviews)
1 Bedroom 1 Bathroom
Family Friendly Cabin
  • Pool
  • Balcony/Terrace
  • Pet Friendly
R1,637/Night For 7 Nights R11,451
10.0
Exceptional
(87 Reviews)
1000 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
R6,638/Night For 7 Nights R46,463
9.0
Exceptional
(1 Review)
2249.66 ft² 10 Guests 3 Bedrooms 3 Bathrooms
House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
R9,861/Night For 7 Nights R69,029
10.0
Exceptional
(2 Reviews)
10 Guests 4 Bedrooms 3 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
R9,431/Night For 7 Nights R66,014
10.0
Exceptional
(79 Reviews)
8 Guests 4 Bedrooms 2 Bathrooms
Ocean View House
  • Fireplace/Heating
  • Ocean View
  • Balcony/Terrace
R6,258/Night For 7 Nights R43,802
10.0
Exceptional
(77 Reviews)
1800 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Fireplace/Heating
  • Pool
R7,452/Night For 7 Nights R52,171

Williamsburg Large Vacation Homes

9.6
Exceptional
(4 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Villa
  • Fireplace/Heating
  • Pool
  • Kitchen
R3,905/Night For 7 Nights R27,332
9.3
Exceptional
(83 Reviews)
227.24 ft² 18 Guests 9 Bedrooms 10 Bathrooms
Group Friendly Bed & Breakfast
  • Fireplace/Heating
  • Balcony/Terrace
  • View
R4,193/Night For 7 Nights R29,353
8.0
Excellent
(4 Reviews)
4 Guests 1 Bedroom 1 Bathroom
Family Friendly Villa
  • Fireplace/Heating
  • Pool
  • Kitchen
R2,884/Night For 7 Nights R20,192
9.1
Exceptional
(296 Reviews)
324.57 ft² 34 Guests 14 Bedrooms 14 Bathrooms
Bed & Breakfast
  • Fireplace/Heating
  • Balcony/Terrace
  • View
R2,694/Night For 7 Nights R18,861
New
2400 ft² 9 Guests 5 Bedrooms 3 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
R12,600/Night For 7 Nights R88,193
10.0
Exceptional
(39 Reviews)
1545 ft² 10 Guests 3 Bedrooms 2 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
R2,926/Night For 7 Nights R20,478
10.0
Exceptional
(18 Reviews)
1531 ft² 10 Guests 3 Bedrooms 3 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
R4,174/Night For 7 Nights R29,218
10.0
Exceptional
(13 Reviews)
10 Guests 3 Bedrooms 2 Bathrooms
Ocean View Condo
  • Oceanfront
  • Spa
  • Fireplace/Heating
R7,726/Night For 7 Nights R54,091

Why Choose Rent By Owner for your Williamsburg 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 Williamsburg

When should you plan your Vacation Rentals stay?

Choosing the right time to visit can enhance your experience in this destination, allowing you to enjoy its unique charm and attractions at their best while conveniently securing your ideal vacation rentals here.

Peak Season Highlights

spring
Spring (March to May)

During this time, the area comes alive with pleasant weather and blooming gardens, making it ideal for exploring historic sites and enjoying outdoor activities. You can expect moderate daytime temperatures that make sightseeing comfortable.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
autumn
Fall (September to November)

This season offers cooler temperatures and vibrant fall foliage, perfect for experiencing the region's rich history amidst scenic views. The weather remains mild, encouraging outdoor adventures and cultural festivals.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December to February)

Visiting during the winter provides a quieter experience with fewer crowds and lower prices. The cooler weather is suitable for indoor exploration and enjoying cozy accommodations in the historic district.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
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Summer (June to August)

While summer sees higher temperatures and increased tourist activity, you can enjoy longer days and lively events. It's the best time for those who appreciate warm weather and outdoor entertainment in the area.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F

Weekly Weather Forecast for Williamsburg

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.

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 grilling with a fully equipped barbecue area for memorable meals under the open sky.
  • Relax by a private swimming pool that offers refreshing relief during warm summer days.
  • Spend time in beautifully maintained gardens or landscaped yards to unwind and soak up the sun.
  • Take advantage of spacious patios or decks perfect for outdoor dining and entertaining guests.
  • Utilize dedicated outdoor parking areas to conveniently accommodate your vehicles during your stay.
  • Explore nearby walking trails or nature paths for outdoor adventures within the region.
  • Benefit from outdoor recreation facilities such as basketball hoops, horseshoe pits, or play areas for added enjoyment.
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Family Activities

  • Colonial Williamsburg: Immerse your family in living history through engaging reenactments and interactive exhibits at this historic area.
  • Busch Gardens Williamsburg: Enjoy a day filled with thrilling rides, live entertainment, and family-friendly attractions in the region's premier amusement park.
  • Water Country USA: Cool off and have fun with water slides and lazy rivers perfect for all ages in this popular water park nearby.
  • The College of William & Mary: Explore the picturesque campus and participate in family-friendly events held at one of the nation’s oldest universities in this area.
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Adult Activities

  • Historical Site Tours: Explore iconic landmarks and reenactments that bring the area's rich history to life, offering a deep connection to its colonial past.
  • Wine and Craft Beer Tastings: Indulge in tasting sessions at local wineries and breweries, savoring unique regional flavors within the region’s vibrant beverage scene.
  • Golfing Experiences: Play on world-class golf courses that provide a relaxing and scenic setting perfect for both leisure and skill sharpening.
  • Shopping and Dining: Discover charming boutiques and renowned restaurants, offering authentic local cuisine and handcrafted goods to enhance your stay here.

Williamsburg Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local History: Take time to visit nearby historical sites to enrich your understanding of the area's rich colonial heritage.
  • Plan Ahead for Attractions: Book tickets in advance for popular attractions to save time and ensure you experience all the region has to offer.
  • Discover Hidden Gems: Venture beyond the main streets to find unique shops, local eateries, and less crowded spots that showcase the area's charm.
  • Enjoy Your Accommodation's Location: Choose a rental situated conveniently to key attractions, allowing you to relax and maximize your sightseeing time.

Transportation Options

  • Car Rental Services: Convenient options for exploring the area at your own pace, with various providers offering flexible rental terms nearby.
  • Public Transit Buses: An economical way to navigate the region, connecting popular attractions and accommodations seamlessly.
  • Rideshare Services: Reliable transportation through applications that provide easy access to nearby vacation rentals and local sites.
  • Taxi Cabs: Readily available for quick trips within the area, ensuring comfortable transport from your vacation rental to key destinations.

Local Customs Options

  • Greeting Etiquette: Expect warm welcomes and friendly exchanges, reflecting the region’s historic hospitality that you’ll experience during your stay.
  • Dining Customs: When enjoying traditional Southern cuisine here, it's customary to leave a small tip and engage in polite conversation with locals and restaurant staff.
  • Historic Dress Codes: For visits to preserved sites and reenactments, dressing modestly and comfortably is appreciated to honor the area's rich colonial history.
  • Celebration Traditions: Participating in local festivals and commemorations often includes wearing period attire or engaging in community activities that celebrate this destination's heritage.

Frequently Asked Questions About Williamsburg?

2. How many vacation rentals have private pools in Williamsburg?

There are 335 vacation rentals with private pools near Williamsburg. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Williamsburg are best for families?

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

4. How many Rentbyowner vacation rentals are available in Williamsburg?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 2088 in the Williamsburg 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 Williamsburg. 

5. What is the cancellation policy for vacation rentals in this area?

The cancellation policy varies depending on the property listing. It's best to review the specific terms outlined in the listing details or contact the property owner directly to understand the applicable rules and any potential fees.

6. How do I inquire about availability and confirm my booking?

Availability can be checked directly through the listing page. Once you find a suitable property, you can send an inquiry or proceed with the booking process online. For detailed questions, reaching out to the host ensures your concerns are addressed before confirming.

7. Are there any additional fees or deposits required when booking here?

Additional fees such as cleaning, service charges, or security deposits might apply and are specified in the listing. Review these details carefully before completing your reservation to ensure transparency and avoid surprises.

8. What amenities and facilities should I expect during my stay?

Amenities vary by property but typically include essentials like Wi-Fi, kitchen access, and parking. You can find a comprehensive list of available amenities in the property description—contact the host if you have particular requirements.

9. Is there a minimum stay requirement for booking a vacation rental in this destination?

Minimum stay policies depend on the individual property. The details are noted in each listing, so it’s advisable to check the duration requirements before making your reservation or contacting the host for clarification.

Williamsburg Top Rated Vacation Rentals

10.0
Exceptional
(72 Reviews)
875 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly Condo
  • Private Pool
  • Fireplace/Heating
  • Pool
R4,107/Night For 7 Nights R28,746
10.0
Exceptional
(65 Reviews)
3 Guests 1 Bedroom 1 Bathroom
Family Friendly Condo
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
R4,013/Night For 7 Nights R28,090
10.0
Exceptional
(18 Reviews)
1280 ft² 6 Guests 2 Bathrooms
Family Friendly Resort
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
R3,524/Night For 7 Nights R24,671
10.0
Exceptional
(13 Reviews)
535 ft² 4 Guests 1 Bathroom
Family Friendly Resort
  • Fireplace/Heating
  • Pool
  • Kitchen
R2,708/Night For 7 Nights R18,962
10.0
Exceptional
(11 Reviews)
10 Guests 3 Bathrooms
Family Friendly Resort
  • Hot Tub
  • Fireplace/Heating
  • Pool
R5,400/Night For 7 Nights R37,790
10.0
Exceptional
(10 Reviews)
1542 ft² 10 Guests 3 Bedrooms 2 Bathrooms
Group Friendly Condo
  • Hot Tub
  • Pool
  • Air Conditioner
R7,212/Night For 7 Nights R50,487
10.0
Exceptional
(10 Reviews)
1531 ft² 10 Guests 3 Bedrooms 3 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
R4,552/Night For 7 Nights R31,862
10.0
Exceptional
(9 Reviews)
10 Guests 3 Bedrooms 3 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
R3,772/Night For 7 Nights R26,406