Williamsburg Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Williamsburg vacation rentals

Stylish Private Suite in the heart of Brandywine Valley

Stylish Private Suite in the heart of Brandywine Valley

Stylish Private Suite in the heart of Brandywine Valley
Wilmington
10.0 out of 10, Exceptional, (195)
"Great time and friendly people "
United States
Karl
The price is ￥20,214
￥30,919 total
includes taxes & fees
Dec 14 - Dec 15
Stylish Private Suite in the heart of Brandywine Valley
Exterior
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront
Perryville
10.0 out of 10, Exceptional, (20)
"Great waterfront home with sunset views! Plenty of space for our group, very clean, and the hot tub was a perfect bonus. Peaceful, relaxing, and just as described. We’d definitely come back!"
United States
Kaylyn G.
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront
2 bedrooms, WiFi
Private townhouse near downtown and state park

Private townhouse near downtown and state park

Private townhouse near downtown and state park
Downtown Wilmington
9.4 out of 10, Exceptional, (11)
"Great little spot in a perfect location for us"
United States
j m.
The price is ￥25,049
￥43,747 total
includes taxes & fees
Dec 15 - Dec 16
Private townhouse near downtown and state park
Smart TV, books
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Earleville
9.8 out of 10, Exceptional, (59)
"We had an amazing weekend at the cottage. It’s very clean and beautiful! The close walk to the beach is perfect and we had great weather. Would love to stay here again! "
United States
Angela F.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach
Captivating Chesapeake experience

Captivating Chesapeake experience

Captivating Chesapeake experience
Perryville
10.0 out of 10, Exceptional, (279)
"Nothing more beautiful than staying by the water at Joe’s place!Such a wonderful place to unwind and refuel!"
United States
Doreen H.
Captivating Chesapeake experience
Fridge, microwave, oven, stovetop
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

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

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Wilmington
8.8 out of 10, Excellent, (13)
"Very quiet place with comfortable bed. Great overnight stay!"
United States
Rhonda Y.
The price is ￥15,394
￥26,972 total
includes taxes & fees
Dec 14 - Dec 15
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Property grounds
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

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

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Elkton
9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Fridge, microwave, oven, stovetop
Two-story condo in luxury townhouse. Free parking.

Two-story condo in luxury townhouse. Free parking.

Two-story condo in luxury townhouse. Free parking.
Downtown Wilmington
9.6 out of 10, Exceptional, (16)
"This is a great place and super conveniently located. We loved all the amenities! Special shout out for the lovely towels! We would definitely stay here again!"
United States
Shelly S.
The price is ￥33,586
￥55,622 total
includes taxes & fees
Dec 14 - Dec 15
Two-story condo in luxury townhouse. Free parking.
Fridge, microwave, oven, stovetop
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Elkton
9.8 out of 10, Exceptional, (44)
"This was our second time staying here and we really love it! It has everything needed and is very close &convenient to any outing we did, The house layout works great for our group of six. Already planning our next trip!! "
United States
Susan G.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is ￥50,239
￥94,129 total
includes taxes & fees
Dec 15 - Dec 16
5-bedroom vacation home 5 minutes from historic Charlestown
Outdoor dining
Chesapeake Bay House with Dock & Private Beach

Chesapeake Bay House with Dock & Private Beach

Chesapeake Bay House with Dock & Private Beach
Elkton
10.0 out of 10, Exceptional, (180)
"We loved this house and had the best time!!"
United States
Laura C.
Chesapeake Bay House with Dock & Private Beach
Spa
Stunning waterfront villa with indoor pool and kids swing set and play area.

Stunning waterfront villa with indoor pool and kids swing set and play area.

Stunning waterfront villa with indoor pool and kids swing set and play area.
Earleville
9.8 out of 10, Exceptional, (20)
"Had a good time, grandkids never came out of the pool"
United States
Michael D.
Stunning waterfront villa with indoor pool and kids swing set and play area.
Fridge, microwave, oven, stovetop
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is ￥20,991
￥53,072 total
includes taxes & fees
Dec 13 - Dec 14
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Fridge, microwave, oven, stovetop
Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
Tiny Home Tranquil Oasis
Marina
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is ￥12,595
￥38,403 total
includes taxes & fees
Dec 15 - Dec 16
Historic Chesapeake City Stay
Fridge, microwave, oven, stovetop
Homey Retreat in Historic Kennett Square!!

Homey Retreat in Historic Kennett Square!!

Homey Retreat in Historic Kennett Square!!
Kennett Square
10.0 out of 10, Exceptional, (85)
"One of the nicest properties we have stayed at. Fantastic amenities. Highly recommend!!"
United States
Stephen
The price is ￥29,543
￥49,819 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Homey Retreat in Historic Kennett Square!!
1 bedroom
Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.6 out of 10, Exceptional, (5)
"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."
United States
Rees L.
The price is ￥12,696
￥25,322 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Summer Rustic Camping with AC and King Bed
Property grounds
Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is ￥10,884
￥17,306 total
includes taxes & fees
Dec 22 - Dec 23
Country Get Away 1 Bedroom Apartment
Fridge, microwave, oven, stovetop
Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal
Chesapeake City
10.0 out of 10, Exceptional, (72)
"Great house close to canal and downtown Chesapeake City!"
United States
Michael M.
Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal
Interior
Charming 2-bedroom cabin close to Fair Hill on horse farm

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

Charming 2-bedroom cabin close to Fair Hill on horse farm
Elkton
9.6 out of 10, Exceptional, (14)
"Excellent stay! "
United States
Edward S.
Charming 2-bedroom cabin close to Fair Hill on horse farm
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

Hampton Inn & Suites Wilmington Christiana

Hampton Inn & Suites Wilmington Christiana

10/10 Excellent
"It was a convenient place to stay. Staff was very welcoming. Room was clean and met my needs."
Valerie 1-night trip
Posted 2 days ago
Hampton Inn & Suites Wilmington Christiana

Find out more about Williamsburg

Search for holiday rentals in Williamsburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Williamsburg using one of the methods below:

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Look no further and take a look at our great range of rental properties in Williamsburg!

Frequently asked questions

Can I find a vacation rental in Williamsburg?

Yes, we have vacation rentals close to top points of interest in Williamsburg, or you can go with a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental that Williamsburg has to offer?

Stylish Private Suite in the heart of Brandywine Valley: This vacation home rental outside of Williamsburg offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Dragon Run Park. Lums Pond State Park and Kirkwood Soccer Complex are a couple of places you'll find in the larger area.

What’s a vacation rental in Williamsburg like?

Vacation rentals are private properties where you can stay for a long or short time in Williamsburg. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for families.