Williamsburg Vacation Rentals

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Vacation Rentals in Williamsburg

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, 36 reviews
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, 89 reviews
"Myself, mom, sister, and friend came down for the weekend to participate in the Mammoth March held at the Fair Hill Park. The house was nice and close, clean, and comfortable."
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, 20 reviews
"Thoroughly enjoyed our stay! Betty is such a great host. Beautiful area...GREAT sunsets and close to the beach! Very comfortable weekend stay! Also close to some great wineries and Alpaca farms!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
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Chesapeake City Overlook: Breathtaking View!
10.0 out of 10, Exceptional, 5 reviews
"Lovely home and hostess! Very clean and responsive. Beautiful water views. Excellent vacation home"
Chesapeake City Overlook: Breathtaking View!
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, 89 reviews
"Our Family decided to take a last minute Spring Break trip and had a fantastic time. Matt was a great host and easy to communicate with. We were pleasantly surprised by all of the local dining options. Despite terrible weather that we experienced, we made the best of our trip and had a great time."
Waterfront house with amazing views. Top of the Chesapeake
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, 20 reviews
"This was the perfect house for 3 Dads and their 14-15 yr olds for a weekend lacrosse tournament. The house was clean and spacious. The owner went over and above to welcome us and make us feel at home. The boys loved the kayaks, swimming and the beach. The Dads enjoyed the outdoor area, fire pit and grilling. All the beach supplies were on hand. Easy and quick communications with the owner."
Beachfront Sunsets on the Water at Oakwood Beach
Homey Retreat in Historic Kennett Square!!
10.0 out of 10, Exceptional, 45 reviews
"We had a lovely stay and hope to return. The house was exactly what we want in a vacation rental. It had charm and personality, was located within walking distance of cafes and restaurants and was very comfortable for the four of us. Communication with Ivanna was seamless. Our family has a wonderful stay."
The price is CA $272
CA $461 total
includes taxes & fees
Jul 8 - Jul 9
Homey Retreat in Historic Kennett Square!!
Clean and Cozy 2 BR home blocks away from downtown
10.0 out of 10, Exceptional, 15 reviews
"Great house, very clean. Only a short few minute walk to restaurants and shops and parks."
Clean and Cozy 2 BR home blocks away from downtown
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
9.8 out of 10, Exceptional, 36 reviews
"House was very clean and in an excellent location. However the grounds were in need of weeding to the point that the advertised upper bay view was blocked or partially blocked from many areas. Host was prompt in responding when I reached out."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Top of the Chesapeake - Minutes from Historic Charlestown
9.8 out of 10, Exceptional, 128 reviews
"Three generations from PA, CO and VT all converged on the "Top of the Chesapeake" and had a lovely time. This is a stellar place for bird watching since it's between a creek and the upper Bay ("river".) Kayaks were a hit with 12 year olds and their parents. The owner's very reasonable rules and guidelines were so easy and he was available for help. Highly recommend this place!"
The price is CA $490
CA $892 total
includes taxes & fees
Jul 8 - Jul 9
Top of the Chesapeake - Minutes from Historic Charlestown
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, 28 reviews
"Pretty house with plenty of room. Easy check in and out."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
9.6 out of 10, Exceptional, 155 reviews
"This River property is a little bit of Paradise away from home! It is everything and more as advertised! My husband and I leased the property for 5 nights for a family reunion, ages 1 to 89 years old! My family of 5, my Mom, Dad and Grandmother, my brothers family of 4 and my nieces family of 3. The house was big enough for all of us to be together or everyone could have their own space. We enjoyed the pool, the hot tub, the playground and the sunsets across the river were amazing. My...
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
Entire place with private parking
7.8 out of 10, Good, 6 reviews
"Overall great location, space and with secure parking."
The price is CA $135
CA $217 total
includes taxes & fees
Jun 26 - Jun 27
Entire place with private parking
Hidden Gem! - Downtown
2.0 out of 10, 1 review
"Small AC that would not cool the upstairs, where bedrooms are. Receptacles were hazardous. Check the street view on Google Maps."
Hidden Gem! - Downtown
Thunder Hill Retreat - Peaceful - sleeps 12
10.0 out of 10, Exceptional, 6 reviews
"We stayed at this property for the week of University of Delaware’s graduation. It was perfect, about a 15 minute drive from Newark, in a very nice neighborhood. The house was in a lovely wooded area near a creek, where we were able to take walks in the neighborhood. The house was clean and comfortable and the host, Raymond, made it easy. I would highly recommend."
The price is CA $300
CA $703 total
includes taxes & fees
Jun 26 - Jun 27
Thunder Hill Retreat - Peaceful - sleeps 12
Private townhouse near downtown and state park
10.0 out of 10, Exceptional, 5 reviews
"The home was very clean and smelled nice. Neighbors are very friendly as well!"
The price is CA $244
CA $473 total
includes taxes & fees
Jul 1 - Jul 2
Private townhouse near downtown and state park
Two-story condo in luxury townhouse. Free parking.
9.8 out of 10, Exceptional, 9 reviews
"This spot was awesome. Stayed here for a lacrosse tournament. It was perfect for our coaching staff. Easy check in. Clean. Everything you’d need. 100% would recommend and 100% would return."
The price is CA $328
CA $514 total
includes taxes & fees
Jul 1 - Jul 2
Two-story condo in luxury townhouse. Free parking.
Luxe Modern Townhome Near Downtown Wilmington!
10.0 out of 10, Exceptional, 11 reviews
"My daughter was graduating from university of Delaware so we rented this place in Wilmington. Pretty easy drive back-and-forth from Newark to Wilmington. The place was clean and comfortable and plenty of room for our five-person family. The kitchen was very nice and easy to use as well. The only issue was no patio furniture in the back deck area."
Luxe Modern Townhome Near Downtown Wilmington!
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
9.8 out of 10, Exceptional, 11 reviews
"We had a great time here. House is beautiful and was very peaceful to be right on the lake!"
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
A cottage on the shore of the Delaware River
9.8 out of 10, Exceptional, 56 reviews
"Such a nice little property on a great beach- was very private, great sunsets, Beth is awesome- def would recommend!"
A cottage on the shore of the Delaware River
Don't see what you're looking for?
See all available properties in Williamsburg
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.

Other types of properties in Williamsburg you may be interested in

Sheraton Suites Wilmington Downtown
3.5 star property
8.2 out of 10, Very good, 1,000 reviews
"Location."
The price is CA $185
CA $203 total
includes taxes & fees
Jul 7 - Jul 8
Sheraton Suites Wilmington Downtown
Red Roof Inn & Suites Newark - University
2.0 star property
5.8 out of 10, 1,005 reviews
"Check-in started off rocky as I had just driven 7 hours and was given a different type of room than I had booked. However, the balcony (and luckily great weather) made up for that. Yes, it is a beaten-up old motor hotel, but it was terrific overall. Dogs welcome, quiet (except for intermittent morons with loud cars on S College), felt safe, cute coffee maker, and the BED WAS FANTASTIC!"
The price is CA $101
CA $112 total
includes taxes & fees
Jun 26 - Jun 27
Red Roof Inn & Suites Newark - University
SureStay Plus Hotel by Best Western Brandywine Valley
2.5 star property
6.6 out of 10, 1,001 reviews
"It’s great experience."
The price is CA $122
CA $135 total
includes taxes & fees
Jun 26 - Jun 27
SureStay Plus Hotel by Best Western Brandywine Valley
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Williamsburg. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Waterfront house with amazing views. Top of the Chesapeake: This vacation home rental outside of Williamsburg is located on the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 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 Lums Pond State Park. Glasgow 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.

Recent reviews of Williamsburg properties
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