Holiday houses in Surry

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Top-rated holiday rentals in Surry

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

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Top Guest favourite
A well-appointed bedroom features a spacious bed with a textured white cover. Colorful accent pillows add depth to the decor. A wooden dresser stands against one wall, while a bedside lamp illuminates the space. Natural light filters through a window adorned with light curtains.
Home in Smithfield

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

FamilyLocationPets

4.97 out of 5 average rating, 331 reviews
Top Guest favourite
Home in Charles City

Cap 2 Cap Cottage VA Capital Trail Charles City

Cap 2 Cap Cottage - Rural oasis awaits in a NEWLY RENOVATED COTTAGE on 6 acres. 52 mile Virginia Capital Trail (Jamestown - Richmond) is only 3/10 of a mile away.Primary suite w/ 1 King bed. Add'l bedroom w/ 1 Queen bed. 2 full baths. Great Wifi, Smart TV, fully equipped kitchen, private deck. Fantastic restaurant/brewery Indian Fields Tavern is 3 miles away. Perfect stay for cyclists ,history lovers or just unwinding. NO Smoking or parties. Colonial Williamsburg 24 miles, Richmond is 30 miles .

LocationValueBarbecue

4.99 out of 5 average rating, 138 reviews
Top Guest favourite
A serene waterfront view of the James River is presented, with a soft layer of mist hovering over the water. A wooden pier extends into the river, lined with posts, while trees and grass frame the scene, enhancing the tranquil atmosphere.
Cottage in Surry

“Magnolia Cottage” on the River

Perched on a bluff high above the James River this charming rehabbed cottage is an idyllic escape from everyday life. This spot is for travelers who seek a step back in time to a simpler life. You’ll be surrounded by woods, water and a growing flower farm. The set up is unique in that the cottage itself holds living and sleeping space while your own designated bathroom and outdoor hot water shower are a short walk across the yard to a tool shed turned luxury bath and shower under the open sky.

FamilyLocationBathroom

4.9 out of 5 average rating, 104 reviews
Top Guest favourite
A serene cottage, surrounded by lush greenery, features a welcoming front porch with chairs and warm lighting. A gravel pathway leads to the entrance, highlighting the harmony between the home and its natural surroundings.
Farm stay in Smithfield

Cozy Farm Cottage with Horses, Fire Pit, & Trails

Escape to Timberline Ranch, a 30-acre horse farm near historic Smithfield. Horses and goats are visible from multiple windows. Your bedroom is cozy with room-darkening drapes, plenty of blankets and pillows. The kitchen is well stocked. Coffee station stocked and to-go cups. Bathroom has a ceiling heater, towel warmer, essentials. W/D with detergent. Step out to the front porch rocking chairs, fire pit (wood incl), and picnic table. Explore trails, follow the creek, and hunt for hidden gnomes.

ValueLocationBeach

5.0 out of 5 average rating, 194 reviews
Top Guest favourite
A historic house is set amidst gentle greenery, featuring a white exterior with multiple chimneys and a welcoming porch. A white picket fence encircles the lush yard, enriched by tall trees and seasonal foliage, creating a serene and inviting environment.
Home in Williamsburg

History Art and Nature-110 Acres of Ancient Forest

WILLIAMSBURG AREA, SURRY, VA. CELEBRATE AMERICA'S 250TH by living in the historic family home of a Revolutionary War soldier! Lightwood Forest is a beautiful historic house nestled in 110 acres of private woodland preserve. Surround yourself with history, antiques, art and nature, and over two miles of private hiking trails. Lightwood Forest is in rural Surry County, on the south side of the James River, a short, free car ferry ride from Williamsburg and Jamestown, which runs 24/7, all year.

FamilyValueBathroom

5.0 out of 5 average rating, 145 reviews
Superhost
A cozy living room is presented with a patterned area rug featuring wildlife motifs. Comfortable seating is available with a futon and a patterned couch. A wooden coffee table sits in the center, and a television is mounted on the wall, accompanied by natural light from nearby windows.
Home in Surry

Uncle Bill's Lodge & Soccer Pool Showdown

Uncle Bill welcomes your group to the comforts of the lodge & outdoor games in the heart of Surry! 3 bedroom, 2 bath home sleeps up to 12 guests! Complimentary smores kit for guests! Outdoor fun includes Soccer Pool, Archery range, Tetherball, Cornhole & kiddie hobbit house complete with tonka trucks, dinosaurs, kitchen play things & chalk to amuse the little ones. The backyard is fenced & ready to welcome your furry friends! Enjoy the fresh air & an open sky of stars with no light pollution!

ValueFamilyTV

4.79 out of 5 average rating, 86 reviews
Top Guest favourite
A circular fire pit is surrounded by stone blocks, with logs burning brightly in the center. Smoke gently rises into the air, and the area is bordered by grass and a quiet wooded backdrop.
Home in Surry

Surry Homeplace

Located a few miles from the ferry to Williamsburg, and one mile from Chippokes State Park, this home has the feel of camping with all the amenities of home! Inside you will find washer and dryer, wifi (this is dish wifi - Zoom will not work and sometimes it is spotty), two full bathrooms, and a fully stocked kitchen. Outside offers a fire pit, a charcoal grill, a fenced area for pets / limit 2 (30 pound max dog, NO CATS ) and plenty of room for parking. Smoking is NOT allowed in the house.

ValueFamilyHospitality

4.98 out of 5 average rating, 129 reviews
Top Guest favourite
The exterior of a large black barn is shown under a clear blue sky. Two wooden doors are open, revealing a welcoming entrance. Flower pots are arranged along the path, while two wooden chairs are positioned in front, inviting relaxation amidst a tranquil rural setting.
Farm stay in Charles City

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.

LocationFamilyBreakfast

4.99 out of 5 average rating, 161 reviews
Guest favourite
A spacious living area features large windows providing views of Gray's Creek. A comfortable sofa and a cozy chair are positioned alongside a coffee table on a decorative rug. A private balcony is accessible through sliding glass doors, enhancing the connection to the scenic surroundings.
Apartment in Surry

The Hotel at The Surry Seafood Co Room 1

Beautiful efficiency hotel room overlooking Gray's Creek in Surry, VA with separate living and sleeping rooms. Private queen bed with walkin closet. Living area with pull out queen size sofa. Kitchenette with refrigerator and microwave in each room. Situated above a very nice seafood restaurant. Private balcony overlooks the marina and marshes. Fishing pier and public boat launch on site. Sleeps 4. Private entrance. 5.3% Sales tax will be added to final pricing per local laws.

LocationValueLayout

4.84 out of 5 average rating, 125 reviews
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.
Apartment in Williamsburg

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.

LocationFamilyQuiet

4.83 out of 5 average rating, 520 reviews
Guest favourite
An inviting bedroom features a spacious bed with white linens, accentuated by decorative pillows in various colors. A woven headboard adds texture, while two lamps sit on turquoise nightstands. Soft light filters through the plantation shutters on either side of the bed, enhancing the serene atmosphere.
Home in Surry

Two King Suites - Bunk Rm - Ferry

Welcome to The Scotland Shore House! Conveniently located next to the Scotland Ferry dock, we are just a 20 minute scenic ferry ride into historic Jamestown. Enjoy the beautiful 180° views of the James River while relaxing with the whole family. You will be approximately: 25 mins from Jamestown 30 mins from Williamsburg 40 mins from Bush Gardens 50 mins from Yorktown 7 mins from Chippokes State Park 60 mins from Richmond International Airport 75 mins from VA Beach

FamilyLocationGetting around

4.99 out of 5 average rating, 69 reviews
Top Guest favourite
An outdoor area features a small red Tiny House beside a clear pool. Two shaded seating areas are provided with umbrellas, along with a picnic table and a swing. Open green space extends beyond, bordered by trees, creating a natural setting.
Tiny home in Wakefield

Cute 1-bdrm tiny house in the country w/firepits

Enjoy the sounds of nature at this Studio-style Tiny House with heat for wintry nights and air conditioning. Tiny House features a kitchenette with a mini fridge, microwave, portable electric stove, coffee pot and grill. Plus a kitchen sink and running deep well water. Relax on the porch. This sleeps 2 privately and with a full size bed and a sleeper sofa. Inside you will find a new toilet for your convenience, plus a outdoor bathroom, shower and wash station.

LocationFamilyQuiet

4.95 out of 5 average rating, 103 reviews

Popular amenities for Surry holiday rentals