Holiday rentals in Williamsburg

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Top-rated holiday rentals in Williamsburg

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Top guest favourite
Guest house in Gloucester
5 out of 5 average rating, 163 reviews

Summer Waterfront • Dock, Pool, & Kayaks

A waterfront summer retreat tucked into 10 secluded wooded acres above Bland Creek, perfect for long days and relaxed evenings - Screened porch with water views and cool creek breezes - A Pool is available for rent for private use - Firepit evenings, and true outdoor living - Dock, kayaks, fishing, and direct water access -Outdooring dining options and family-friendly - Immaculately clean and thoughtfully stocked for a seamless stay - Peaceful setting just minutes from downtown Gloucester

Guest favourite
A warm living area is captured, featuring a comfortable leather couch and a cozy yellow chair. A bottle of wine and two glasses are placed on the counter next to a sign inviting guests, while soft lighting creates a welcoming ambiance.
Guest house in Gloucester Point
4.93 out of 5 average rating, 133 reviews

BlueBird Nest

Keep it simple at this peaceful and centrally-located oasis, tucked away in coastal Virginia. Our newly renovated 1BR/1BA barn apartment on 3 acres is ideal for those who want to live like a local. We are 3 miles from the heart of the American Revolution in Yorktown, and Yorktown Beach, and a short drive to area attractions in the Historic Triangle. Unwind after a day of exploring with a glass of wine on the balcony or enjoy the firepit and the view. This is an upstairs apartment with stairs.

Top guest favourite
The exterior of the house is illuminated by warm string lights, showcasing a spacious two-story structure. Adirondack chairs surround a central fire pit on a gravel patio, providing a cozy gathering area against a backdrop of tree line.
Home in Williamsburg
4.99 out of 5 average rating, 150 reviews

Cheerful 3-bedroom house with parking on premises

Have fun with the whole family at this cozy place. Conveniently located 2 minutes from the Great Wolf Lodge and 10 minutes from Busch Gardens, Colonial Williamsburg, the College of William and Mary, and several parks, this three-bedroom, three baths, big-basement stand alone house lets you explore “the Burg” hassle-free and recharge in a restful space on the back of the Waller Mill reservoir woods. The yard features beautiful landscaping, a large fire pit with solo stove & cozy backyard lights.

Top guest favourite
A two-story blue home is surrounded by trees, featuring a spacious deck with railings accessible from the upper level. A gravel patio area with chairs and a fire pit is visible on the ground level, complemented by neatly maintained greenery.
Home in Gloucester Point
4.97 out of 5 average rating, 157 reviews

Charming coastal home w/ outdoor area and river views

Tucked away at the end of a quiet road, our home welcomes you. This spacious, thoughtfully designed 1 BR/1.5 BA home on 4 acres is ideal for those looking to relax and get away from it all while still being just minutes away from some of the areas best dining and attractions. Whether you want to watch the sun rise over the York River, spend the day exploring the Williamsburg historic triangle (Busch Gardens), or just take it easy around the house and enjoy the outdoor area, the choice is yours.

Top guest favourite
A modern house stands amidst a lush green landscape, featuring a combination of dark and light exterior finishes. Large windows allow natural light to flood in, with a stone path leading to the entryway. The surrounding area is filled with trees, enhancing the home's natural setting.
Home in Toano
4.94 out of 5 average rating, 135 reviews

Serenity Over 5 Acres: Historic Triangle Haven

*4500 sq.ft. fully furnished house w/ 4 bedrooms & loft. *Includes all the amenities you need to enjoy a peaceful stay. * Unwind w/ friends & family in this modern retreat nestled on 5 acres in the woods w/ waterfront view & a fire pit. *You’ll enjoy the secluded area & yet be close to the bustle & hustle of what Williamsburg can offer. *Only 15-20 minutes to major attractions such as, Colonial Williamsburg, Bush Gardens, Jamestown, Yorktown, outlet mall. *Master bathroom only has a bath tub

Guest favourite
A serene landscape captures a sunset over the James River, with vibrant hues of orange and pink reflecting on the water. Silhouettes of trees frame the view, and a gently sloping green lawn leads toward the riverbank, enhancing the tranquil atmosphere.
Apartment in Williamsburg
4.94 out of 5 average rating, 143 reviews

Luxury Riverfront Condo w/ sunrise & sunset views

Luxury One Bedroom Condo with stunning views of sunrises and sunsets overlooking the James River. Perfect for a romantic getaway or a small family adventure, you can sit on the private balcony and enjoy the serene views of the river and the marina, or venture out for kayaking, jet ski, pontoon boat, Busch Gardens, historic Colonial Williamsburg, wineries, award winning golf courses and restaurants, spa and so much more. Come and experience an unforgettable vacation while making many memories.

Top guest favourite
A serene view of the water showcases the Rappahannock River and surrounding landscape. The horizon blends various shades of blue with green grass and patches of marshland, inviting a sense of tranquility. Wisps of clouds drift across the expansive sky.
Guest house in White Stone
5 out of 5 average rating, 285 reviews

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

Top guest favourite
A red kayak rests at the edge of the serene reservoir, surrounded by trees that frame the waterway. The calm surface reflects the clear blue sky and soft ripples created by a gentle breeze, ensuring a tranquil outdoor experience.
Cottage in Lanexa
4.97 out of 5 average rating, 150 reviews

TooFine Lakehouse, pet friendly waterfront cottage

Cute & cozy (tiny) waterfront cottage nestled in a pine forest. Situated on an almost 3 acre point on the Diascund Reservoir this is THE perfect spot to get away from it all & still be in the middle of everything! Options abound - fishing from the dock, bird watching, canoeing, roasting marshmallows around the fire pit, swinging in the hammocks, napping on the screened in porch, grilling on the patio, reading in the loft, playing games (inside & out), or just chill & feel the vibe.

Superhost
The exterior of a cozy apartment is depicted, featuring a white facade with green shutters. A small porch is visible, accompanied by a sign indicating the apartment's name. Lush greenery and floral plants frame the entrance, while a gravel pathway leads to the door.
Flat in Williamsburg
4.84 out of 5 average rating, 487 reviews

The Nook

Enjoy a getaway in this cozy 1 bedroom apartment attached to a classic 1940s Cape Cod home minutes from Colonial Williamsburg and Jamestown. You'll be within biking distance to many local attractions such as Williamsburg Winery, Jamestown Island, Jamestown Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The Nook was completely refinished in 2020. Need more space or traveling with a group? Inquire about our other units.

Top guest favourite
The living area features a light grey sofa, two teal armchairs, and a wooden coffee table. A woven basket holds a soft throw. In the background, a kitchenette is visible, along with cabinets and appliances, illuminated by natural light from skylights.
Apartment in Williamsburg
4.96 out of 5 average rating, 125 reviews

2 Bedroom Stylish Kingsmill condo

Located in the beautiful Kingsmill resort, this charming two bedrooms, two baths condo with stunning seasonal views over the pond is only a few minutes away from CW, Busch Gardens, water country, William and Maryand other Williamsburg attractions. All Kingsmill amenities are not included as they are strictly for Kingsmill residents Guests have access to the Spa and to the Mill Coffee House which is within walking distance from the condo and serves breakfast and lunch every day..

Top guest favourite
A lush field is filled with blooming yellow flowers under a clear blue sky. In the background, a red barn is situated near a fence, surrounded by trees that provide a natural border to the landscape.
Farm stay in Williamsburg
4.97 out of 5 average rating, 391 reviews

3 BR Cottage on Mallardee Farm in Williamsburg

Enjoy all the comforts of home during your Williamsburg vacation at Mallardee Farm! Allow us to make our home, your home while you explore all of Williamsburg’s attractions-just a 15 minute drive away! You’ll find that Mallardee Farm will serve as its own attraction with our friendly, rescued farm pets, walking trails through the 57 acre property, complimentary fishing poles, canoe, row boat & kayaks to use on our 7 acre pond. Covid-19 precautions followed.

Top guest favourite
A single-story home is positioned on a grassy lot, surrounded by trees and bushes. A wooden staircase leads to the front porch, which is flanked by red shutters on the windows. The roof is gently pitched, and a clear blue sky with scattered clouds is visible above.
Home in Williamsburg
4.97 out of 5 average rating, 255 reviews

Casita on the Corner

The Casita is a cozy 2 bedroom, one bath, small dog friendly home is on a corner lot in a family friendly neighborhood just minutes from major attractions like Busch Gardens-Water Country. The area is rich with historical sites. Be sure to visit Colonial Williamsburg, Jamestown and Yorktown. There is a shopping center with a Grocery store and restaurants within walking distance from the property.

Popular amenities for Williamsburg holiday rentals

When is the best time to visit Williamsburg?

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Avg. price$82 SGD$82 SGD$78 SGD$76 SGD$154 SGD$81 SGD$80 SGD$83 SGD$200 SGD$310 SGD$294 SGD$196 SGD
Avg. temp5°C6°C9°C15°C19°C24°C26°C25°C22°C16°C11°C7°C

Frequently Asked Questions

  • What are the best places to stay in Williamsburg?

    Historic downtown Williamsburg has charming homes and easy access to major attractions. For a peaceful setting, look for accommodations near Kingsmill or in neighborhoods with tree-lined streets and walking paths.

  • What are the best things to do in Williamsburg with kids?

    Explore Colonial Williamsburg for immersive, interactive history, visit the engaging exhibits at the Jamestown Settlement, or enjoy outdoor activities and rides at Busch Gardens Williamsburg. Many families also explore local nature trails and hands-on museums.

  • What are some of the best things to do in Williamsburg?

    Explore living history at Colonial Williamsburg, stroll the grounds of the College of William & Mary, and take in art at the Muscarelle Museum. Around town, sample regional cuisine and enjoy outdoor markets or gardens.

  • How is the weather in Williamsburg?

    Williamsburg has cool winters, with January highs around 49°F (10°C), and warm, humid summers peaking near 87°F (31°C) in July. Rain is spread throughout the year, so a light rain jacket can be useful.

  • What are the best places to visit in Williamsburg?

    Colonial Williamsburg is one of the most popular sites for its historic streets and reenactments. The Governor's Palace, Jamestown Settlement, and the Art Museums of Colonial Williamsburg are also frequently suggested.

  • What are some hiking trails in Williamsburg?

    Explore shaded paths at the Greensprings Greenway Interpretive Trail, wooded loops in Waller Mill Park, or scenic boardwalks through New Quarter Park. Many local trails feature wetlands, forests, and birdwatching opportunities.

  • What are some family activities we can do in Williamsburg?

    Families often explore interactive sites at Colonial Williamsburg, bike or walk local trails, or enjoy rides and shows at Busch Gardens Williamsburg. The Virginia Living Museum nearby has hands-on animal exhibits and nature trails.

  • What are some of the best day trip ideas from Williamsburg?

    Many visitors explore Yorktown’s riverfront and American Revolution history, sample wines around the Williamsburg Winery, or wander the coastal scenery and museums in Newport News and Norfolk. Jamestown Island has historic and natural sites to explore.

  • Are there any pet friendly accommodations available in Williamsburg?

    Williamsburg has a range of pet-friendly stays in areas near local parks and trails. Many hosts welcome pets, especially in neighborhoods around downtown or close to green spaces.

  • What are some local tips for visiting Williamsburg?

    Consider wearing comfortable shoes for exploring cobblestone streets and expansive historic grounds. Early mornings and weekdays are quieter at major sites, and local markets and food trucks showcase regional flavors.

  • What is Williamsburg known for?

    Williamsburg is known for its well-preserved colonial history, living history museums, and educational reenactments. The city also has vibrant arts, universities, and beautiful green spaces.

  • What are the best hidden gems to explore in Williamsburg?

    Explore the peaceful trails at Freedom Park, discover unique public art around downtown, or relax at the Secret Gardens at the Williamsburg Botanical Garden inside Freedom Park. Some visitors enjoy the quiet galleries at the Stryker Center.

  • What are the best foods to try in Williamsburg?

    Williamsburg has dishes inspired by colonial recipes, like peanut soup and spoon bread, as well as Chesapeake Bay seafood such as local oysters and crab cakes. Regional farmers’ markets highlight local produce and baked goods.

  • What should I bring for a trip to Williamsburg?

    Bring comfortable walking shoes, a reusable water bottle, and attire for both indoor and outdoor activities. Depending on the season, a rain jacket and sun protection are often useful.

  • What is the nightlife in Williamsburg like?

    Williamsburg's nightlife includes relaxed taverns, local breweries, and live music venues downtown. Some spots feature outdoor patios, open-mic nights, and regional craft beverages.

  • What are the most popular events or festivals in Williamsburg?

    Many people attend the Grand Illumination in the winter for fireworks and festivities, the An Occasion for the Arts festival in early fall, and seasonal celebrations at Colonial Williamsburg throughout the year. Food and wine festivals around town draw visitors as well.

  • Are there family friendly vacation rentals in Williamsburg?

    Williamsburg has many family-friendly vacation rentals, with options near parks, museums, and outdoor spaces. Larger homes and properties with access to shared amenities are often available in neighborhoods around town.

  • When is the best time to visit Williamsburg?

    Spring and fall are often recommended for comfortable temperatures and outdoor events. Summer brings festivals and green landscapes, while winter invites smaller crowds and a festive downtown atmosphere.

Quick stats about holiday rentals in Williamsburg

  • Total holiday rentals

    Explore 3,590 holiday rentals in Williamsburg

  • Nightly prices starting at

    Williamsburg holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 14,490 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,090 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    1,690 properties feature pools

  • Rentals with dedicated workspaces

    2,800 properties have a dedicated workspace

  • Wifi availability

    3,590 of Williamsburg holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Pet-friendly, Self check-in and Laptop-friendly workspace across Williamsburg rentals

  • 4.6 Average rating

    Williamsburg stays receive an average rating of 4.6 out of 5 from guests

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