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Williamsburg Holiday Rentals

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Our top choices for Williamsburg holiday rentals

1. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (47 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is NZ$188
includes taxes & fees
9 Sept - 10 Sept
Country Get Away Studio Apartment

2. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (29 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is NZ$473
includes taxes & fees
1 Sept - 2 Sept
Historic Chesapeake City Stay

3. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is NZ$393
includes taxes & fees
1 Sept - 2 Sept
Nature's Haven Tiny Home

4. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
The price is NZ$405
includes taxes & fees
1 Sept - 2 Sept
Tiny Home Tranquil Oasis

5. Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is NZ$570
includes taxes & fees
1 Sept - 2 Sept
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

6. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is NZ$631
includes taxes & fees
1 Sept - 2 Sept
Elegant Family Stay • Quiet Neighborhood • Comfort

7. Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is NZ$319
includes taxes & fees
6 Sept - 7 Sept
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

8. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
10.0 out of 10, Exceptional, (3 reviews)
"Great stay. Awesome owner. Nice restaurant right up the ramp. Would def recommend and do again if in the area!!!"
United States
Justin M.
The price is NZ$487
includes taxes & fees
2 Sept - 3 Sept
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

9. Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is NZ$600
includes taxes & fees
21 Sept - 22 Sept
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

10. Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is NZ$272
includes taxes & fees
1 Sept - 2 Sept
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

11. New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.6 out of 10, Exceptional, (29 reviews)
"We love this townhouse, close to everything!"
United States
Judy P.
The price is NZ$314
includes taxes & fees
8 Sept - 9 Sept
New Construction townhome close to everything downtown w/transparent pricing

12. Cozy Pet Friendly House

Cozy Pet Friendly House
Wilmington
The price is NZ$313
includes taxes & fees
1 Sept - 2 Sept
Cozy Pet Friendly House

13. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
10.0 out of 10, Exceptional, (1 review)
The price is NZ$345
includes taxes & fees
14 Sept - 15 Sept
Cozy 1-bedroom apartment in Lincoln University

14. Entire place with private parking

Entire place with private parking
Cool Spring
8.0 out of 10, Very good, (11 reviews)
"great place very clean. Will stay again loved private parking "
United States
kennya J.
The price is NZ$263
includes taxes & fees
21 Sept - 22 Sept
Entire place with private parking

15. Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.6 out of 10, Excellent, (22 reviews)
"Great location with character! Host was friendly and communicated well."
United States
Ross G.
The price is NZ$784
includes taxes & fees
1 Sept - 2 Sept
Kennett Square, Near Longwood Gardens & Downtown

16. Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants

Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants
Downtown Wilmington
9.0 out of 10, Wonderful, (2 reviews)
"There was leak from upstairs the day before but they had cleaned it all up except for a really sticky floor. Traffic was load but a great location. Tricky getting the garage pass with no parking in front. I recommend indications for pulling around the corner and running in for the parking pass."
United States
Jon N.
The price is NZ$292
includes taxes & fees
3 Sept - 4 Sept
Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants

17. Private Suite w/sitting room in the heart of Brandywine Valley

Private Suite w/sitting room in the heart of Brandywine Valley
Wilmington
10.0 out of 10, Exceptional, (211 reviews)
"Just perfect !"
United States
Cloudi
The price is NZ$363
includes taxes & fees
1 Sept - 2 Sept
Private Suite w/sitting room in the heart of Brandywine Valley

18. Modern Downtown 1BR | Free Garage Parking + Workspace

Modern Downtown 1BR | Free Garage Parking + Workspace
Downtown Wilmington
7.4 out of 10, Good, (3 reviews)
"We were in town for a wedding at Hotel DuPont. The proximity to the hotel was amazing! The apartment was cozy and clean. Felt very safe and loved that you needed a code just to enter the main door at the entrance to the building. The host was great and responded quickly to any questions. Having free parking was also a huge plus!! Definitely recommend and would stay again if ever in town."
United States
Aileen R.
The price is NZ$387
includes taxes & fees
2 Sept - 3 Sept
Modern Downtown 1BR | Free Garage Parking + Workspace

19. Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Pennsville Township
The price is NZ$517
includes taxes & fees
1 Sept - 2 Sept
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

20. Underground Railroad Barn

Underground Railroad Barn
Kennett Square
9.8 out of 10, Exceptional, (40 reviews)
"Very cool place! "
United States
Scott M.
The price is NZ$532
includes taxes & fees
14 Sept - 15 Sept
Underground Railroad Barn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Williamsburg Hotel Reviews

Find out more about Williamsburg

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Williamsburg holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Williamsburg. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Williamsburg. Seeing all the best attractions is bound to make you fall in love with Williamsburg. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Williamsburg short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Williamsburg?

Yes, there are holiday rentals close to the most popular sights in Williamsburg, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Williamsburg has to offer?

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This holiday home rental outside of Williamsburg is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

What’s there to see and do in Williamsburg?

While exploring the area, visit family-friendly sights like Frightland, or get outside and enjoy nature at Kirkwood Soccer Complex. Lums Pond State Park and Brookside Shopping Center are a couple of places you'll find in the wider area.

What’s a holiday rental in Williamsburg like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Williamsburg. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.