Williamsburg Holiday Rentals

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Holiday Rentals in Williamsburg

Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!

10.0 out of 10, Exceptional, (18)
"Super cute! We came in for a lax tournament. Perfect place to unwind."
Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!

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

Cottage on Cabin Creek

10.0 out of 10, Exceptional, (100)
"I highly recommend staying here for a cozy couples weekend. It was absolutely beautiful and quiet. The host was so nice and made us feel welcome. I can’t wait to stay here again."
The price is AU$566
includes taxes & fees
11 Dec - 12 Dec
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

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$689
includes taxes & fees
2 Dec - 3 Dec
Luxury on the river, steps to downtown &boat ramp!

Beautiful Peaceful Home

7.4 out of 10, Good, (3)
"Owner canceled the day before with no notice"
Beautiful Peaceful Home

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

10.0 out of 10, Exceptional, (6)
"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$609
includes taxes & fees
16 Dec - 17 Dec
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

Downtown Oxford | Bikes | Pet Friendly

9.6 out of 10, Exceptional, (9)
"The house was perfectly located, close to central Oxford and the riverfront, as well as close to Doc's Sunset Grill, which was nice! The bikes came in handy and were used frequently to explore the area. There were a couple of things that could help for another guest. One, more coffee cups. Also, it would be helpful to mention that the coffee maker is standard and not a Keurig type of coffee maker. We brought a lot of K-cups and couldn't use them and had to go out and buy regular coffee. Not...
Downtown Oxford | Bikes | Pet Friendly

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, (9)
"Awesome "
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (29)
"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)

Cambridge Beach Home on Choptank River w/ Pier!

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. "
Cambridge Beach Home on Choptank River w/ Pier!

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)
"Private and quiet but very close to Easton and St Michels. Just the two of us (70 years old) and we liked it a lot. Can imagine it would be wonderful for a family of energetic kids."
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

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.
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, (1065)
"Anniversary. Great time. Beautiful property "
The price is AU$370
includes taxes & fees
2 Dec - 3 Dec
Hyatt Regency Chesapeake Bay

Days Inn & Suites by Wyndham Seaford

2.0 star property
6.6 out of 10, (696)
"Food"
The price is AU$108
includes taxes & fees
9 Dec - 10 Dec
Days Inn & Suites by Wyndham Seaford

Days Inn & Suites by Wyndham Cambridge

2.5 star property
6.6 out of 10, (1010)
"easy location"
The price is AU$103
includes taxes & fees
1 Dec - 2 Dec
Days Inn & Suites by Wyndham Cambridge
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.
Beautiful view of the beach with palm trees

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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 Kiwanis 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.