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Top Holiday Rentals in Williamsburg

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (2)
"Great, cozy, quiet little spot! Perfect for 4 adults and a baby. My 1.5 year old loved exploring the deck with an amazing water view, and gained lots of confidence navigating the little steps throughout the house and worked on her balance. Kitchen was well appointed and suited our needs. Would stay here again!"
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Charming 2-bedroom cabin close to Fair Hill on horse farm

10.0 out of 10, Exceptional, (1)
"Good experience"
The price is £473
includes taxes & fees
8 Jul - 9 Jul
Charming 2-bedroom cabin close to Fair Hill on horse farm

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (175)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (41)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (265)
"This place is the definition of the perfect getaway for a quick weekend. The home is immaculate, the scenery is beautiful and we feel instantly relaxed here. "
Captivating Chesapeake experience

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (161)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (162)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
Nancy’s Touch, A Waterfront Paradise!

Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer

Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (83)
"My friends and I wanted a relaxing getaway with beautiful views and that is exactly what we got. Sue was so wonderful and when there was a massive snowstorm expected to come on our arrival date, she offered to change the dates to accommodate us. Everything was wonderful and we had the best stay."
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (50)
"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Private townhouse near downtown and state park

10.0 out of 10, Exceptional, (9)
"The house is clean and comfortable with many amenities and within walking distance of parks and restaurants and museums. The host was very easy to connect with."
The price is £229
includes taxes & fees
2 Jul - 3 Jul
Private townhouse near downtown and state park

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (38)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (2)
"Enjoyed"
The price is £176
includes taxes & fees
2 Jul - 3 Jul
Nature's Haven Tiny Home

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

8.8 out of 10, Excellent, (5)
"Was in Wilmington to work a trade show at the Chase Center on the Riverfront. Everything was as described and the communications with the host were great. Only about a 12 minute drive to the venue and lots of restaurants within a 10 minute drive. It’s nothing fancy but for about the same price as a budget hotel room you get a kitchen, two comfy bedrooms and a living room. "
The price is £156
includes taxes & fees
15 Jul - 16 Jul
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is £454
includes taxes & fees
2 Jul - 3 Jul
5-bedroom vacation home 5 minutes from historic Charlestown

Kennett Square, Near Longwood Gardens & Downtown

7.8 out of 10, Good, (10)
"Great place, very difficult check in process. It was a nice stay overall "
The price is £370
includes taxes & fees
2 Jul - 3 Jul
Kennett Square, Near Longwood Gardens & Downtown

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

8.4 out of 10, Very good, (13)
"Thanks Sean "
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Cozy 2-bedroom townhome in charming Elkton

8.8 out of 10, Excellent, (5)
"We stayed for two nights and the beds were very comfortable. The house met our needs for the short time we were in town. I do wish somewhere it was disclosed that it backed up to a railroad track that is used day and night for commuter rail and we had a large freight train come by both nights at roughy 345am. "
Cozy 2-bedroom townhome in charming Elkton

Cozy on the Hill. Close to Riverfront, Brandywine park and great food

9.6 out of 10, Exceptional, (14)
"The unit was perfect for our stay. It was spacious and clean. The location was great, close to restaurants and easy access to major roadways."
Cozy on the Hill. Close to Riverfront, Brandywine park and great food
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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Frequently asked questions

Can I find a holiday rental 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?

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This holiday home rental outside of Williamsburg is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

What’s there to see and do in Williamsburg?

While exploring the area, visit family-friendly sights like Fred Rust Ice Arena, or get outside and enjoy nature at Kirkwood Soccer Complex. Lums Pond State Park and New Castle 100 Archers are a couple of places you'll find in the wider area.

What’s a holiday rental in Williamsburg like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Williamsburg. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.