Williamsburg Holiday Rentals

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Holiday Rentals in Williamsburg

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (15)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is NZ$666
includes taxes & fees
20 Oct - 21 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

9.8 out of 10, Exceptional, (7)
"Great House "
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Sailwinds Loft at Cambridge Creek

9.8 out of 10, Exceptional, (16)
"The location and apartment were perfect. "
The price is NZ$436
includes taxes & fees
14 Oct - 15 Oct
Sailwinds Loft at Cambridge Creek

Station House East: Upscale Loft in the Historic District Cambridge, MD

The price is NZ$434
includes taxes & fees
22 Oct - 23 Oct
Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

8.8 out of 10, Excellent, (5)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
The price is NZ$523
includes taxes & fees
8 Oct - 9 Oct
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

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"
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF 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."
The price is NZ$1,130
includes taxes & fees
8 Oct - 9 Oct
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

10.0 out of 10, Exceptional, (11)
"Amazing "
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

2.5 star property
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
The price is NZ$655
includes taxes & fees
20 Oct - 21 Oct
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
9.8 out of 10, Exceptional, (9)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
The price is NZ$614
includes taxes & fees
20 Oct - 21 Oct
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

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"
Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

Walk to Dtwn: Waterfront Eastern Shore Townhome!

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

Casa Maria heart of downtown Cambridge Maryland

9.8 out of 10, Exceptional, (10)
"Place was quiet and clean. Few minutes drive from the center of town. Definitely a great experience!"
Casa Maria heart of downtown Cambridge Maryland

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (42)
"The house was great with a wonderful river view! Easily accommodated 5 adults."
Stylish Home on the Choptank River (with Tidal Beach)

New 2 bedroom apartment. Quiet setting, Just bring your suitcase and enjoy.

New 2 bedroom apartment. Quiet setting, Just bring your suitcase and enjoy.

Cambridge Apt in Walkable Neighborhood

3.0 star property
Cambridge Apt in Walkable Neighborhood

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

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

Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River

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"
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River

3-bedroom waterfront retreat in Secretary, Maryland

10.0 out of 10, Exceptional, (2)
"Nicely decorated"
3-bedroom waterfront retreat in Secretary, Maryland

Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18

10.0 out of 10, Exceptional, (79)
"We loved our stay at Eaglehaven! We had 3 generations that enjoyed the expansive home. Plenty of fun table games, plenty of quiet nooks for napping and reading, plenty of space to enjoy the beautiful pool and yard! A well stocked kitchen was a bonus! "
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
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

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$434 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?

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina: This holiday home rental outside of Williamsburg is located in the city centre, and has a garden, a selection of games and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Williamsburg?

While exploring the area, visit family-friendly sights like T.S. Smith & Sons, or get outside and enjoy nature at Long Wharf Park. Layton's Chance Vineyard and Winery and Bill Burton Fishing Pier State Park 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.