Williamsburg Holiday Rentals

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Holiday Rentals in Williamsburg

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
9.6 out of 10, Exceptional, (5)
"Our 3 night stay was absolutely perfect for our family of six! As a native of the area I was thrilled to be able to come back to my home town and stay right in the heart of downtown Cambridge. There are several restaurants and shops within walking distance and great views of downtown. The space was great, comfortable beds, and modern updates. Our host Jen was responsive and made sure we had everything we needed. We will definitely be back! "
The price is AU$539
includes taxes & fees
24 Feb - 25 Feb
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

10.0 out of 10, Exceptional, (55)
"The family had a lovely time. The home was beautiful and the landscape surrounding the home was magnificent. "
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
9.6 out of 10, Exceptional, (4)
"Very clean, well stocked with towels, paper products and everything else you need. Lots of space for a large group. I liked the master bedroom on the first floor. Having a second coffee maker upstairs is a nice touch. Walking distance to downtown. "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (31)
"We just finished a great three day stay at this property. The place was spotless and the location to the towns of the eastern shore was perfect. Wonderful to look out and see the river lazily roll by. The"
Stylish Home on the Choptank River (with Tidal Beach)

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!

Sailwinds Loft at Cambridge Creek

10.0 out of 10, Exceptional, (1)
"The place is tucked away on the upper floor of a business near boat piers and a cool old church. Head up the stairs and you are met with a really nice apartment, with interesting decor, very clean, well laid-out, and with very spacious bedrooms. We had a nice and comfortable stay (including good beds and pillows). Be advised, though, that there are some sloped ceilings upstairs and tricky stairs to the upstairs bedroom suite, so it's best to be careful not to trip or bump your head (as I did...
The price is AU$373
includes taxes & fees
21 Feb - 22 Feb
Sailwinds Loft at Cambridge Creek

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

10.0 out of 10, Exceptional, (74)
"We were very impressed with the property and your place was very clean and had just about everything we needed. The location is wonderful and close to the event that we stayed in Cambridge for. I would definitely recommend this for others and will likely be renting again"
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18

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$558
includes taxes & fees
24 Feb - 25 Feb
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

10.0 out of 10, Exceptional, (4)
"Really comfortable home in a quiet neighborhood! All of the beds are comfortable, the laundry was convenient and the grounds are lovely. The managers have been easy to work with. We'll be back!"
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

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

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

NEW! Gorgeous Waterfront Estate with pool, beach and dock

9.6 out of 10, Exceptional, (5)
"Great House "
NEW! Gorgeous Waterfront Estate with pool, beach and dock

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

2.5 star property
10.0 out of 10, Exceptional, (8)
"Beautiful historic place and great location and vibe in the heart of downtown. Great beds, nice quality sheets, fun games, stellar wood doors. Wonderful place! 10 stars!"
The price is AU$587
includes taxes & fees
24 Feb - 25 Feb
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

6.0 out of 10, (2)
"On this trip, it was only my borfriend and I but this waterfront home in Cambridge is a perfect place to spend time with family and friends with plenty of comfortable sleeping accommodations and several spaces to congregate and visit both inside and outside the house, The home is clean, private, and in a quiet neighborhood. I highly recommend to anyone looking for a place to stay on Maryland’s gorgeous Eastern Shore."
The price is AU$1,057
includes taxes & fees
22 Feb - 23 Feb
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

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

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

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

Downtown Oxford | Outdoor Dining | Character Filled

Downtown Oxford | Outdoor Dining | Character Filled

Cozy 2BR Home near Idlewild Park

10.0 out of 10, Exceptional, (3)
"The apartment was perfect. Spotless, well maintained and equipped. The owners had coffee, fruit bowl and goodies waiting.I would highly recommend this charming and centrally located rental, it’s very likely we would stay here again.Thanks Lynda and Ron."
Cozy 2BR Home near Idlewild Park

Upscale Condo in Historic Downtown Cambridge, Maryland

9.4 out of 10, Exceptional, (3)
"The property itself is lovely, but the neighborhood has seen better days. The city other than the one street with the cafe and mural seems to be vacant and there isn’t much to do for a family with young children other than the park with the light house. But like I said, the home was lovely."
The price is AU$488
includes taxes & fees
2 Mar - 3 Mar
Upscale Condo in Historic Downtown Cambridge, Maryland

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

10.0 out of 10, Exceptional, (10)
"Our extended family of nine spent a week at Warwick Farms in July, 2024. There was space for all of us to be together for meals, puzzles, movies, and games...and also plenty of room for us to spread out and do our own thing. The pool was wonderful, the view was amazing, and the amenities were superb. We appreciated the cleanliness, the plentiful towels, the wildlife sightings, and the availability of the kayaks, etc. We had one small issue during the stay, but the property manager and host...
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
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, (1000)
"Love staying here. The hot tub is great, love the common areas. "
The price is AU$431
includes taxes & fees
24 Feb - 25 Feb
Hyatt Regency Chesapeake Bay

Days Inn & Suites by Wyndham Seaford

2.0 star property
6.6 out of 10, (707)
"Nice, clean room. "
Days Inn & Suites by Wyndham Seaford

Days Inn & Suites by Wyndham Cambridge

2.5 star property
6.6 out of 10, (1003)
"The staff was kind and helpful. "
The price is AU$110
includes taxes & fees
26 Feb - 27 Feb
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.

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?

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*: This holiday home rental outside of Williamsburg is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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. Layton's Chance Vineyard and Winery and Martinak 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.