Holiday rentals in Williamsburg

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Top-rated holiday rentals in Williamsburg

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Apartment in Williamsburg
4.94 out of 5 average rating, 203 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

This beautiful 1 bed-1 bath unit is a cozy 400 sq.ft. and is located in the exclusive Kingsmill neighborhood. This first floor unit offers a king-size bed with a private patio that walks out onto the 9th Fairway of the River Course at Kingsmill. You'll enjoy the luxurious full bathroom with shower/tub combination and upgraded finishes. In the bedroom, you'll also find a computer desk, an over-sized sitting chair, a mini-fridge, a microwave, a Keurig coffee maker, and 50" Roku Smart TV w cable!

Superhost
The home’s exterior is visible through a wooden fence, surrounded by green grass and trees. A gravel driveway leads towards the house, which features a backyard patio space. Vibrant flowers are present in the foreground, adding a touch of color to the lush landscape.
Home in Williamsburg
4.83 out of 5 average rating, 282 reviews

Colonial Retreat

Enjoy a getaway in our 1940 Cape Cod home minutes from Colonial Williamsburg & Jamestown. Within biking distance to many attractions such as Williamsburg Winery, Jamestown Island & Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The house was refinished in 2021; you'll find an updated kitchen, smart TVs, large back patio & front porch. Please read the house rules before booking. No smoking. Need more space? Inquire about our other units

Top guest favourite
A modern cottage is presented in a wooded setting, featuring a spacious deck with seating and a spiral staircase. A fire pit surrounded by four chairs is anchored on a green lawn. Soft outdoor lighting adds to the inviting ambiance of the area.
Guest house in Gloucester County
4.97 out of 5 average rating, 227 reviews

Modern Moody Creekside Cottage w/ HotTub & FirePit

Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

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
4.95 out of 5 average rating, 146 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.

Top 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
4.94 out of 5 average rating, 152 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, 161 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, 173 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.

Guest favourite
Home in Williamsburg
4.86 out of 5 average rating, 327 reviews

Bamboo Bungalo Duplex Near Busch Gardens

Find your home away from home when visiting historic Williamsburg. It feels very private here nestled amongst the bamboo and trees. This is a great location for families with children! We are within 5 minutes of Bush Gardens and Water Country for great family fun outings! For history buffs, we are 7 minutes from Colonial Williamsburg, 15 minutes from Jamestown Settlement and 20 minutes from Yorktown Battlefields. Enhance your stay with a relaxing herbal massage at the on site massage studio!

Guest favourite
Apartment in Williamsburg
4.95 out of 5 average rating, 146 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 bright kitchen sink area is highlighted by a large window featuring multiple panes, allowing natural light to illuminate the space. Various plants and kitchen items are arranged on the countertop, while the outside view reveals greenery, enhancing the serene ambiance.
Farm stay in Charles City
4.99 out of 5 average rating, 152 reviews

Lovely space above barn on a working farm!

Getaway to the country!! Suitable for a 4 adults or families of 5. Wake up to beautiful sunrises. Spend a peaceful day surrounded by farm and wild animals. Enjoy the dark night sky lit with millions of stars after watching the sunset. Above our barn is a two bedroom, one bath living space with a living area open to a kitchen fit for every cook!! Located near Williamsburg, Jamestown and Yorktown, Busch Gardens and Water Country, the Virginia Capitol Trail and 5,217 acre wildlife refuge.

Top guest favourite
An open living space features wooden walls and beams, creating a warm and inviting environment. A gray sectional sofa is placed near a dining table, paired with modern gray cabinetry in the kitchen area. Natural light streams through multiple windows, enhancing the cozy atmosphere.
Cottage in Lanexa
4.97 out of 5 average rating, 157 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.

Top guest favourite
Apartment in Williamsburg
4.96 out of 5 average rating, 136 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..

Popular amenities for Williamsburg holiday rentals

When is the best time to visit Williamsburg?

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Avg. price$180 SGD$158 SGD$80 SGD$76 SGD$155 SGD$81 SGD$80 SGD$84 SGD$201 SGD$312 SGD$295 SGD$197 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 3,520 holiday rentals in Williamsburg

  • Nightly prices starting at

    Williamsburg holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 14,100 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,170 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 70 rentals that welcome pets

  • Holiday rentals with a pool

    1,630 properties feature pools

  • Rentals with dedicated workspaces

    2,830 properties have a dedicated workspace

  • Wifi availability

    3,520 of Williamsburg holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Pet-friendly 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

Destinations to explore

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