Williamsburg Holiday Rentals

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Holiday Rentals in Williamsburg

Cottage on Cabin Creek

10.0 out of 10, Exceptional, (102)
"Lovely quaint property for two. Exactly as described loved our stay. "
The price is AU$584
includes taxes & fees
14 Jan - 15 Jan
Cottage on Cabin Creek

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (30)
"We enjoyed the beautiful views, nature and clean comfortable house with all amenities. Will definitely book again on our next trip to Eastern shore."
Stylish Home on the Choptank River (with Tidal Beach)

Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F

10.0 out of 10, Exceptional, (2)
"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

Newly built riverfront home with dock, kayaks, basketball court, & game room

9.0 out of 10, Wonderful, (4)
Newly built riverfront home with dock, kayaks, basketball court, & game room

Beautiful Peaceful Home

10.0 out of 10, Exceptional, (2)
"I was deciding between booking a hotel or a home and thankful that we decided on this home for our weekend getaway. After visiting the museums in Cambridge, we were welcomed to our home away from home. Very relaxing, comfortable and spacious for our family. Conveniently located to downtown and nice neighborhood. If looking for a home to stay when in the Cambridge area, this is an excellent choice."
Beautiful Peaceful Home

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

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

10.0 out of 10, Exceptional, (7)
"The Lighthouse cottage was super clean & comfortable, beautifully decorated and stocked with supplies, and located on a lovely block overlooking water l. As a bonus, it was walking distance from downtown’s many shops and restaurants. "
The price is AU$674
includes taxes & fees
13 Jan - 14 Jan
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

10.0 out of 10, Exceptional, (3)
"Thank you for a beautiful stay! Well appointed kitchen, comfortable beds and a pristine 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, (10)
"Awesome "
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River

Choptank River Beach Home w/ Pier in Cambridge!

10.0 out of 10, Exceptional, (13)
"We stayed in this beautiful property for a weekend of bike riding in Cambridge. The place was very accurately described in the listing, very clean, nice bathrooms, and the kitchen was very well stocked. Great view of the river from the living room We even enjoyed the kayaks and a late Sept swim in the Choptank. "
Choptank River Beach Home w/ Pier in Cambridge!

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, (14)
"Return visitors loving Seventh Haven ❤️"
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

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

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

1915 Historic Cambridge Property w/ Fire Pit!

9.4 out of 10, Exceptional, (14)
"Nice historic house decoration "
1915 Historic Cambridge Property w/ Fire Pit!

Waterfront Retreat < 4 Mi to Dtwn Cambridge!

10.0 out of 10, Exceptional, (4)
"It was great! We highly recommend! "
Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Stylish Victorian in Historic District

10.0 out of 10, Exceptional, (15)
"This is the second time we have stayed here with our same group of friends. We enjoyed it just as much or more than the first time. Walking distance to all the fun and charm Cambridge has to offer. Well decorated and comfortable. Kieth is a great host and we loved our stay! Can't recommend enough!"
Stylish Victorian in Historic District

Luxury on the river, steps to downtown &boat ramp!

10.0 out of 10, Exceptional, (5)
"Stayed for three nights with a few friends with a focus on birding. The house is in a great location for "
The price is AU$874
includes taxes & fees
20 Jan - 21 Jan
Luxury on the river, steps to downtown &boat ramp!
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
8.8 out of 10, Excellent, (1005)
"My family loves staying at this resort. The pool continues to be AWESOME. The Chesapeake suite we booked this time was great and we asked to change from a king to 2 queens during our stay and the staff was very accommodating. Unfortunately the linens and towels weren’t as comfortable as they’d been in the past. It was a bit difficult to sleep with the stiff sheets. The availability of hot water in the room was a bit variable. None of this is terrible but for the price you pay you want it to be...
The price is AU$366
includes taxes & fees
8 Jan - 9 Jan
Hyatt Regency Chesapeake Bay

Holiday Inn Express Easton, an IHG Hotel

3.0 star property
9.0 out of 10, Wonderful, (550)
"Staff was polite and accommodating."
The price is AU$219
includes taxes & fees
20 Jan - 21 Jan
Holiday Inn Express Easton, an IHG Hotel

Best Western Plus Easton Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (1006)
"Best place on the Delmarva"
The price is AU$192
includes taxes & fees
13 Jan - 14 Jan
Best Western Plus Easton Inn & Suites
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?

Cottage on Cabin Creek: This holiday home rental outside of Williamsburg is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 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.