Williamsburg Holiday Rentals

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Holiday Rentals in Williamsburg

Holiday Home in Cambridge

9.6 out of 10, Exceptional, (19)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
The price is NZ$618
includes taxes & fees
8 Dec - 9 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Holiday Home in Cambridge

9.8 out of 10, Exceptional, (7)
"Wow! What an incredible property and house. We were a group of families with small kids, and it was heaven for them playing in the pool, on the dock, on the playground, and in the expansive yard. Lots of beautiful sunsets on the patio for the grown-ups too. We never had to leave. Can't recommend highly enough. "
United States
Lea F.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Holiday Home in East New Market

3.0 star property
10.0 out of 10, Exceptional, (2)
"Clean, well-appointed kitchen. Loved the crab shack!! Would highly recommend. Used the kayaks and canoe. The pool was perfect! The property is beautiful. Highly reccomend"
United States
kathleen l.
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

Condo in Downtown Cambridge

10.0 out of 10, Exceptional, (6)
The price is NZ$476
includes taxes & fees
12 Dec - 13 Dec
Station House East: Upscale Loft in the Historic District Cambridge, MD

Holiday Home in Cambridge

8.8 out of 10, Excellent, (9)
"This home was everything we needed and more! It was spacious, clean and a beautiful location! There was a leak in the ceiling and the owners were very responsive and fixed it right away. Definitely recommend this stay."
United States
Priscilla A.
The price is NZ$1,173
includes taxes & fees
4 Dec - 5 Dec
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Holiday Home in Easton

10.0 out of 10, Exceptional, (11)
"Great property for a family summer vacation and to just relax by the pool, kayak, fish off the dock, and head to town for ice cream or crabs."
United States
Anonymous traveller
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Holiday Home in Easton

10.0 out of 10, Exceptional, (24)
"Second time we stayed there in a month. Came back because it is a clean, bright, tranquil setting."
United States
Scott B.
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

Apartment in Cambridge

3.0 star property
Cambridge Apt in Walkable Neighborhood

Condo in Downtown Cambridge

8.8 out of 10, Excellent, (5)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is NZ$529
includes taxes & fees
17 Dec - 18 Dec
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Condo in Downtown Cambridge

2.0 star property
9.6 out of 10, Exceptional, (10)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is NZ$629
includes taxes & fees
14 Dec - 15 Dec
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Holiday Home in Cambridge

10.0 out of 10, Exceptional, (38)
"If you're looking for a beautifully appointed, sparkling clean, comfortable vacation, this is it. Almost Heaven did not disappoint. The grounds and pool are stunning. Best sunsets at the dock. We had our boat out every day! Cannot wait to rebook for next year!"
United States
doug s.
Peaceful family get away with in ground pool and hot tub close to town

Apartment in Cambridge

3.0 star property
Walk to Dtwn: Waterfront Eastern Shore Townhome!

Holiday Home in Preston

10.0 out of 10, Exceptional, (43)
"The house was great with a wonderful river view! Easily accommodated 5 adults."
United States
Karen
Stylish Home on the Choptank River (with Tidal Beach)

Cottage in Trappe

3.0 star property
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Holiday Home in Cambridge

2.0 star property
8.2 out of 10, Very good, (13)
"The house was perfect for our family reunion in Cambridge. Close to everything that we wanted to access. We would stay here again if we are back in the area. "
United States
Heike R.
La Casa Azul . with Wi-Fi, AC

Holiday Home in East New Market

10.0 out of 10, Exceptional, (14)
"Great House, perfect for a group retreat in a peaceful location. The pool is fantastic on a hot day and the house has good AC to keep you cool.Would happily stay again"
United States
Ed L.
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River

Holiday Home in Cambridge

Lovely 3-bedroom house AC WiFi in the charming Cambridge, Great Location!!!!

Holiday Home in Cambridge

10.0 out of 10, Exceptional, (79)
"Peaceful week by the water with family. Relaxing by the pool and evening campfires are the way to go"
United States
Jeffrey A.
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18

Holiday Home in Hebron

9.8 out of 10, Exceptional, (8)
"The inside of the home was very clean with cute decor."
United States
April
Century-old home with fenced yard, great front porch & small-town charm

Holiday Home in Oxford

9.8 out of 10, Exceptional, (20)
"Wonderful location for a family reunion. Very close to Oxford but felt nicely secluded. House itself was beautiful and charming, and pool was amazing in this hot weather. Would highly recommend"
United States
Evan C.
Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
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 favorite 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 depends 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 NZ$476 per night. Entering your travel dates in the search wizard you might find 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 holiday rentals 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?

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock: This holiday home rental outside of Williamsburg is located on a river, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade/games room.

What can I see and do in Williamsburg?

While exploring the area, visit family-friendly sights like Ruark Boatworks, or get outside and enjoy nature at Long Wharf Park. Hooper's Landing Golf Course and Governor Ross Mansion are a couple of places you'll find in the wider area.

What are holiday rentals like in Williamsburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Williamsburg. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for families.