Williamsburg Holiday Rentals

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Our top choices for Williamsburg holiday rentals

9.4 out of 10, Exceptional, (3)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is AU$504
includes taxes & fees
30 Dec - 31 Dec
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is AU$169
includes taxes & fees
5 Jan - 6 Jan 2026
Country Get Away 1 Bedroom Apartment
10.0 out of 10, Exceptional, (195)
"Great time and friendly people "
United States
Karl
The price is AU$296
includes taxes & fees
30 Dec - 31 Dec
Stylish Private Suite in the heart of Brandywine Valley

Cabin in Chesapeake City

Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (20)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is AU$372
includes taxes & fees
30 Dec - 31 Dec
Historic Chesapeake City Stay
2.0 star property
8.0 out of 10, Very good, (3)
"This unit is very much as depicted in photos on VRBO site. The neighborhood is interesting and feels safe, and the unit itself is very authentic to residential multi units built, I'm guessing, about 100 years ago. We recommend this place. "
United States
Thomas D.
The price is AU$518
includes taxes & fees
30 Dec - 31 Dec
The Gilpin Getaway | 2BR | Free Coffee | by RedAwning
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is AU$535
includes taxes & fees
30 Dec - 31 Dec
Amazing Modern house with a full kitchen and parking
10.0 out of 10, Exceptional, (16)
"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."
United States
Heidi Z.
The price is AU$672
includes taxes & fees
12 Jan - 13 Jan 2026
Thunder Hill Retreat - Spacious/Deck/Hot tub
The price is AU$395
includes taxes & fees
11 Jan - 12 Jan 2026
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
10.0 out of 10, Exceptional, (4)
"Enjoyed our stay."
United States
Erik H.
The price is AU$414
includes taxes & fees
4 Jan - 5 Jan 2026
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
9.6 out of 10, Exceptional, (21)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is AU$505
includes taxes & fees
30 Dec - 31 Dec
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
8.6 out of 10, Excellent, (17)
"Very quiet place with comfortable bed. Great overnight stay!"
United States
Rhonda Y.
The price is AU$263
includes taxes & fees
3 Jan - 4 Jan 2026
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
10.0 out of 10, Exceptional, (35)
"They had everything you may need there just in case and a great location. Beautiful place to stay!"
United States
William R.
The price is AU$538
includes taxes & fees
6 Jan - 7 Jan 2026
Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens
9.8 out of 10, Exceptional, (8)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is AU$243
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
10.0 out of 10, Exceptional, (38)
"Beautiful "
United States
Dawn M.
The price is AU$670
includes taxes & fees
1 Jan - 2 Jan 2026
Charming Carriage House in the Heart of Kennett
9.6 out of 10, Exceptional, (23)
"Very nice and clean. We do work on Fire Apparatus in the area and this will be my go to spot when in the area."
United States
Peter F.
The price is AU$229
includes taxes & fees
5 Jan - 6 Jan 2026
New Construction townhome close to everything downtown w/transparent pricing

Apartment in Bear

Cozy loft above ink shop
9.6 out of 10, Exceptional, (5)
"Cozy little place to stay that was fully stocked for a fair price compared to others in the area. Plenty of parking and quiet even with the tattoo shop below. The only thing that I would like to have had is a light on the front porch but I used my flashlight on my phone so it wasn’t too bad. I would definitely stay again."
United States
Krystle M.
The price is AU$176
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy loft above ink shop
10.0 out of 10, Exceptional, (1)
"We had a nice stay at this gorgeous house! Very comfortable and nicely appointed."
United States
Jordan K.
The price is AU$1,719
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious 4-bedroom house with backyard oasis
10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
The price is AU$758
includes taxes & fees
7 Jan - 8 Jan 2026
Long Beach Cottage, (romantic couple’s getaway)
8.0 out of 10, Very good, (15)
"Great location with character! Host was friendly and communicated well."
United States
Ross G.
The price is AU$698
includes taxes & fees
2 Jan - 3 Jan 2026
Kennett Square, Near Longwood Gardens & Downtown

Holiday Home in Kennett Square

Underground Railroad 4 Bedroom Farmhouse
9.8 out of 10, Exceptional, (25)
"Very nice and clean! "
United States
Virginie M.
The price is AU$549
includes taxes & fees
1 Jan - 2 Jan 2026
Underground Railroad 4 Bedroom Farmhouse
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

Everything you need to know about Williamsburg holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Williamsburg holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Williamsburg holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Williamsburg holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Williamsburg. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Williamsburg holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Williamsburg holiday rentals we have selected for you start as low as AU$188 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Williamsburg rentals

At Expedia, we put the best Williamsburg holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Williamsburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Williamsburg holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Williamsburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Williamsburg is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 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 a selection of games.

What’s there to see and do in Williamsburg?

While exploring the area, visit family-friendly sights like Fred Rust Ice Arena, or get outside and enjoy nature at Kirkwood Soccer Complex. Lums Pond State Park and Chespeake & Delaware Branch Canal 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.