Vacation rentals in Surry

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Top-rated vacation rentals in Surry

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

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Top guest favorite

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

4.97 out of 5 average rating, 327 reviews

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.

ValueLocationOutdoor spaces

Top guest favorite

A winding gravel pathway is illuminated by soft lighting, bordered by lush greenery. String lights are hung above, casting a warm glow over the area, which is surrounded by trees and plantings. A staircase leads to an elevated area in the background.

Guesthouse in Gloucester County

4.97 out of 5 average rating, 239 reviews

Stylish Creekside Cabin w/ HotTub, Parklike views.

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!

ValueFamilyKitchen

Guest favorite

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

4.9 out of 5 average rating, 101 reviews

“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.

ValueFamilyBreakfast

Top guest favorite

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

5 out of 5 average rating, 188 reviews

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.

LocationValueAccuracy

Top guest favorite

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.

Guesthouse in White Stone

5 out of 5 average rating, 316 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.

FamilyLocationSolo travel

Top guest favorite

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

4.98 out of 5 average rating, 129 reviews

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.

LocationValueHospitality

Guest favorite

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

4.84 out of 5 average rating, 123 reviews

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.

FamilyValueNearby

Top guest favorite

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

4.98 out of 5 average rating, 164 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.

FamilyValueLong stay

Top guest favorite

A serene waterfront view showcases a gently sloping yard leading to a wooden dock. A well-maintained path lined with decorative rocks is seen, along with lush greenery and trees bordering the water's edge, inviting relaxation in a tranquil outdoor setting.

Home in Lanexa

4.96 out of 5 average rating, 237 reviews

Williamsburg Hide-A-Way Creekside

Cozy home, updated decor, full kitchen, 3 bedrooms (all Queen beds), 2 baths overlooking a gorgeous creek that is too beautiful to describe. Minutes from Colonial Williamsburg, Busch Gardens yet rural, private and quaint. Screened, 3 season porch with heat and A/C, gated deck for kids and pet containment, propane grill, fire table, swing set, boat ramp, kayaks. Enjoy a totally relaxing experience with homelike accommodations. **Pet friendly upon owner approval of breed, age, etc.

LocationValueLong stay

Top guest favorite

A wooden dock extends into calm waters, reflecting a soft sunset with pastel hues. A covered boat slip is positioned at the end of the dock, framed by the serene landscape of trees on the horizon.

Home in Charles City

4.86 out of 5 average rating, 138 reviews

Chickahominy Riverside Guest Home By Williamsburg!

Our river-side guest house has everything you will need to enjoy your getaway! Enjoy the river, dock, two kayaks, paddle board, canoe, large game room, portable fire pit, playground, basketball goal and large outdoor sitting area with a gas grill. Located 5-20 mins from the finest wedding venues, nearby wineries; less than an hour to Richmond & 25 minutes to Colonial Williamsburg. Only steps to numerous historic plantations & a few miles from the Virginia Capital bike & walking trail.

ValueLocationCleanliness

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

4.83 out of 5 average rating, 518 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.

FamilyLocationAir conditioning

Top guest favorite

Guesthouse in Gloucester

5 out of 5 average rating, 198 reviews

Summer Escape - Dock, Pool, Firepits, & 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 (open Memorial Day–Labor Day) - Dock, kayaks, fishing, firepits, and direct water access -Outdooring dining options and family-friendly - Immaculately clean and thoughtfully stocked for a seamless stay - Just 15 minutes from downtown Gloucester

LocationFamilyGrill