Williamsburg Holiday Rentals

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Holiday Rentals in Williamsburg

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
10.0 out of 10, Exceptional, (5)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is NZ$628
includes taxes & fees
22 Oct - 23 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, (1)
"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Waterfront, cozy cottage with private pool on 27 acres
9.8 out of 10, Exceptional, (87)
"We had a wonderful time overlooking the water and swimming in the refreshing pool while enjoying easy access to downtown Cambridge and Blackwater NW Refuge."
Waterfront, cozy cottage with private pool on 27 acres
Cottage on Cabin Creek
10.0 out of 10, Exceptional, (98)
"Hidden gem. Eastern Shore at its best"
Cottage on Cabin Creek
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
9.8 out of 10, Exceptional, (6)
"We enjoyed our time at the house very much. We went out to dinner only once and the rest of the time we ate in. We grilled two nights and made a roast one night. The views and the pool were more than you could imagine."
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
9.8 out of 10, Exceptional, (55)
"The original home is unique and gorgeous and the additions, the sunroom facing sunrises and the lodge style master chef kitchen gave us plenty of room to spread out. The large lawn and driveway gave us plenty of areas to walk the dogs and the beach was a daily swim spot for the dogs. The pool was one of the nicest we have had yet. We love the places with nice pools facing the boats out on the water. We will be back again for sure"
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
Casa Maria heart of downtown Cambridge Maryland
9.6 out of 10, Exceptional, (5)
"We wanted an overnight on land after a regatta. I misjudged the availability of Uber In Cambridge. End result was a 50 minute walk from the marina. Early departure meant 50 minutes back. Nice apartment. Didn’t spend much time there but got a great shower and comfortable bed. Host was great with communication."
The price is NZ$277
includes taxes & fees
1 Oct - 2 Oct
Casa Maria heart of downtown Cambridge Maryland
Beautiful Peaceful Home
7.4 out of 10, Good, (3)
"Owner canceled the day before with no notice"
Beautiful Peaceful Home
Cambridge Beach Home on Choptank River w/ Pier!
10.0 out of 10, Exceptional, (14)
"This place was perfect for our group of 9. Super well equipped. There wasn't a single thing we needed that it didn't have. Lovely!"
Cambridge Beach Home on Choptank River w/ Pier!
Downtown Oxford | Bikes | Pet Friendly
9.6 out of 10, Exceptional, (9)
"This is a great home for exploring Oxford, MD and the Eastern Shore. The home was very clean, comfortable, and dog friendly. "
Downtown Oxford | Bikes | Pet Friendly
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
10.0 out of 10, Exceptional, (2)
"We had a great stay here! Bonnie was very responsive and helped make our stay comfortable and fun. The kids loved the pool, including big inflatable slide. The yard is so huge and nice. We enjoyed this property a lot!"
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
10.0 out of 10, Exceptional, (8)
"Very nice place to unplug for a single larger family. Pool, fishing and hanging out provide relaxing time."
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
Indian Fields - 25-Acre Nature Lovers retreat!
8.8 out of 10, Excellent, (12)
"This was our third summer at Indian Fields. We love this property. The kids can safely ride their bikes and swim in the pool morning till dark. It was too windy for boat fishing, but we caught a lot of crabs right off the dock! This is an older house with lovely nooks and crannies where the kids play hide and seek. We really appreciated the charging ports on every nightstand. There’s also a new smoke detector but be warned…it is VERY sensitive. Always turn on the stove fan, even just to make a...
Indian Fields - 25-Acre Nature Lovers retreat!
Modern Country Home with Pool and Game Room
9.2 out of 10, Wonderful, (5)
"Awesome place ! We had some family visit us there and everyone loved the place too. The toilet paper holder in the half bath needs to be reattached to the wall. Also … I noticed the drain pipe closest to the hot tub is separated at the top. "
Modern Country Home with Pool and Game Room
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
10.0 out of 10, Exceptional, (13)
"We just returned home from our 8-night stay at this property and enjoyed it tremendously throughout. The setting is beautiful, with seats at the pier for when we preferred a waterside view and just next to the house (close to the wine chiller) for watching the sunsets. Very spacious, well-decorated, comfortable, very well-stocked kitchen which made meals a breeze. We enjoyed it thoroughly (as did our two cockers!) and will look it up again if we're ever heading back to the Eastern Shore."
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
Modern Cambridge Cottage: Walk to Town, Waterfront
10.0 out of 10, Exceptional, (6)
"Only negative is the too small barn door for the bathroom. Studio works great for 2 people. Corporate owned. "
Modern Cambridge Cottage: Walk to Town, Waterfront
-A travelers cottage - A place to rest after a busy day.
10.0 out of 10, Exceptional, (25)
"We wanted a place not far from parks along the bay and this place fit our needs perfectly."
-A travelers cottage - A place to rest after a busy day.
Downtown Oxford | Outdoor Dining | Character Filled
10.0 out of 10, Exceptional, (3)
"The house interior was very nice. It was clean and comfortable. It was well supplied. Close to town and could walk if you wanted to. We would stay there again. Possibly on the porch the dead plants could be removed. However, the screened in porch was very nice to sit in."
Downtown Oxford | Outdoor Dining | Character Filled
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.
10.0 out of 10, Exceptional, (4)
"We were familiar with Woodwind from a previous stay and delighted to return to this restful spot to enjoy time with our family, friends and each other. The property is beautifully situated across the Tred Avon from Oxford and we enjoyed boating there for lunch or simply cruising around the local creeks. The house had everything we needed. I only wish we hadn't packed so much kitchenware because the kitchen was very well equipped for anything - right down to a garlic press! From sipping...
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.
NEW! Gorgeous Waterfront Estate with pool, beach and dock
9.6 out of 10, Exceptional, (4)
"The property was perfect for our family get together. We had a baby, toddler, preschooler, elementary and teens, moms, dads and grandparents. There was a place for everyone. Having a pack n’ play available would have been nice, but we procured one elsewhere. The property was large and felt very private, but Cambridge was just a quick drive."
NEW! Gorgeous Waterfront Estate with pool, beach and dock
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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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Other types of properties in Williamsburg you may be interested in

Hyatt Regency Chesapeake Bay
4.0 star property
8.6 out of 10, Excellent, (1002)
"Easy check in and check out! Would like more than one towel at the pool but had a really nice time. The staff was friendly and professional."
The price is NZ$433
includes taxes & fees
23 Oct - 24 Oct
Hyatt Regency Chesapeake Bay
Days Inn & Suites by Wyndham Cambridge
2.5 star property
6.6 out of 10, (990)
"Cracked tile in bathroom, old bathroom fixtures, srained grout. Wrinkled and discolored bedding. Otherwise clean, quiet, night staff can be mote welcoming maybe better versed at computer check in system to not generate 5 check in receipts with expedia likely why he was not as welcoming."
The price is NZ$114
includes taxes & fees
30 Sept - 1 Oct
Days Inn & Suites by Wyndham Cambridge
Days Inn & Suites by Wyndham Seaford
2.0 star property
6.6 out of 10, (658)
"It was amazing and we enjoyed our stay at the place. "
The price is NZ$119
includes taxes & fees
1 Oct - 2 Oct
Days Inn & Suites by Wyndham Seaford
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.

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 Easton Cycle and Sport, or get outside and enjoy nature at Bill Burton Fishing Pier State Park. Dorchester County Visitors Center and Choptank River Lighthouse 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.