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Top Holiday Rentals in Williamsburg

Our top choices for Williamsburg holiday rentals

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

8.6 out of 10, Excellent, (7)
"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 £143
includes taxes & fees
28 Aug - 29 Aug
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (170)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (11)
"Always a nice get away…."
The price is £212
includes taxes & fees
28 Aug - 29 Aug
Historic Chesapeake City Stay

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (142)
"Very beautiful with private waterfront. Roomy and clean. Like another world away ."
The price is £493
includes taxes & fees
1 Sept - 2 Sept
5-bedroom vacation home 5 minutes from historic Charlestown

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

9.2 out of 10, Wonderful, (5)
The price is £239
includes taxes & fees
25 Aug - 26 Aug
Charming 2-bedroom cabin close to Fair Hill on horse farm

Sailor's Sunrise Cottage - Chesapeake Bay

9.6 out of 10, Exceptional, (51)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay

Stay & Play at Our Beautiful Retreat

10.0 out of 10, Exceptional, (3)
"This property has everything you need for a friends weekend. Pickelball, pool, basketball, even golf hitting net were all used by our group and we enjoyed the TV room and large outdoor space. Takes a little navigating to get there, but the directions were well done and communication with the owner was great. They were very responsive to all of our questions. Would highly recommend this place for groups."
Stay & Play at Our Beautiful Retreat

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

10.0 out of 10, Exceptional, (7)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Welcome to the Mushroom Capital of the World!

9.8 out of 10, Exceptional, (7)
"The house had everything we needed in the kitchen to make and reheat meals, and the bed was comfortable and could be separated from the living area by a sliding door. We also liked the artistic decor!"
The price is £115
includes taxes & fees
28 Aug - 29 Aug
Welcome to the Mushroom Capital of the World!

Charming Carriage House in the Heart of Kennett

10.0 out of 10, Exceptional, (34)
"Booked and stayed it was a great little place to have while visiting family"
The price is £339
includes taxes & fees
24 Aug - 25 Aug
Charming Carriage House in the Heart of Kennett

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (4)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
The price is £130
includes taxes & fees
25 Aug - 26 Aug
Summer Rustic Camping with AC and King Bed

Homey Retreat in Historic Kennett Square!!

10.0 out of 10, Exceptional, (80)
"So convenient and easy to walk to shops and food! The house is adorable and clean. Looking forward to staying again. "
The price is £248
includes taxes & fees
4 Sept - 5 Sept
Homey Retreat in Historic Kennett Square!!

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (23)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest

Tiny Home Tranquil Oasis

The price is £184
includes taxes & fees
23 Aug - 24 Aug
Tiny Home Tranquil Oasis

Cozy Farmhouse in Greenville, DE

10.0 out of 10, Exceptional, (24)
"Super clean house that’s perfect for a group gathering "
Cozy Farmhouse in Greenville, DE

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (272)
"Beautiful home and setting!"
Captivating Chesapeake experience

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

9.8 out of 10, Exceptional, (6)
"Exactly as advertised and Brad was very helpful/responsive!"
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

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

9.2 out of 10, Wonderful, (179)
"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
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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Top Williamsburg Hotel Reviews

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?

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Williamsburg is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 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 a selection of games.

What’s there to see and do in Williamsburg?

While exploring the area, visit family-friendly sights like Frightland, or get outside and enjoy nature at Kirkwood Soccer Complex. Lums Pond State Park and Battery Park 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.