Vacation rentals in Sperryville

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Top-rated vacation rentals in Sperryville

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Guest favourite

Tiny homes in Reva

4.95 out of 5 average rating, 291 reviews

K-9 Heaven Dogs Run Free

K-9 Heaven ... Get away from the City. Enjoy clean open spaces. Spend time with the horses.They love peppermints. Don't leave your K-9 family at home, It's there vacation too. 100% off leash 20 min away Old Rag Mountain , White Oak Falls and downtown Culpeper. There are so many trails for a wonderful hiking experience. We are with in 10 min of nearby winerys, breweries We are off leash for dogs . Never leave the farm as we have Doordash to bring you whatever you desire, Wine, food anything.

Jun. 7 – 14

$204 CAD per night

Guest favourite

Farm stay in Sperryville

4.98 out of 5 average rating, 121 reviews

The Roost at Upper Nonesuch

New for fall: Pickleball Court!. Located in the foothills of the Blue Ridge Mountains, Upper Nonesuch is the perfect place to get away and relax. Enjoy the serene view of the valley and rolling hills from the large screened-in porch and bedroom, the walking trails, the spring-fed pond on the adjacent farm. Take a short drive and enjoy hiking Old Rag and White Oak Canyon Falls. Explore Sperryville and Culpeper, the many orchards, wineries, breweries, all the Shenandoah Valley has to offer.

Sep. 13 – 20

$211 CAD per night

Guest favourite

Guesthouse in Flint Hill

4.97 out of 5 average rating, 150 reviews

Three Meadows Farm, outdoor views, great location

As you approach the driveway on the private lane, you'll be welcomed by beautiful meadows and rolling hills. Set on 10 acres in a shaded, forest of mature trees it's comfortable year round. There are beautiful mountain views from several locations on the property. It's peaceful and quiet here most of the time. We're conveniently located just minutes from Flint Hill, not much farther to Washington VA, Sperryville and Front Royal. It's a two bedroom/one bathroom apartment above a detached garage.

Oct. 8 – 15

$192 CAD per night

Guest favourite

Guesthouse in Syria

4.95 out of 5 average rating, 329 reviews

Little House on Strother Run

Nestled between Mount Tom and Double Top Mountain and at the edge of the Shenandoah National Forest, Little House is the perfect starting out and ending point for a peaceful and relaxing stay in the Appalachian Mountains. Little House is located at the edge of our 7 acre property. You'll enjoy the bucolic atmosphere of our farmette which includes use of our shared sitting area on Strother Run. The sitting area is shared with the main house which is rented or used by our family periodically.

Aug. 9 – 16

$169 CAD per night

Guest favourite

Home in Sperryville

4.97 out of 5 average rating, 239 reviews

Mountaintop Retreat

A 1958 ranch home with spectacular views, great landscaping, a terrific patio and grill, close to multiple Shenandoah National Park hiking trails, wineries, antique shops and famous restaurants. Private, secluded, ideal for 2 to six people comfortably, but will sleep 8 if needed. Nearby, Quievremont Winery Central Coffee Roasters The Inn at Little Washington The Corner Store with Rapp Pizza Before and After Dark Horse Tavern Three Blacksmiths Off the Grid Blue Door Inn 4-6 wineries

Jan. 31 – Feb. 7

$265 CAD per night

Guest favourite

Guest suite in Culpeper

4.98 out of 5 average rating, 250 reviews

Spacious property-deluxe amenities; hot tub & more

Enjoy the beauty of nature in our beautiful private 2 room suite. Located in Culpeper County Virginia, you are minutes away from world class dining, wineries, great breweries while only 20 minutes from Shenandoah National Park. Retreat to the deck for an evening soak in the hot tub after a day of exploring the area. This space provides a queen bed, plenty of sitting space, full private bathroom, walk in closet, 50 inch smart TV, WIFI, mini fridge, ice maker, microwave, and coffee maker.

Nov. 21 – 28

$160 CAD per night

Guest favourite

Yurt in Etlan

4.95 out of 5 average rating, 192 reviews

Peaceful Secluded Old Rag Retreat

The spacious one bedroom yurt is located high on a forested hillside in the middle of 15+ acres. Come enjoy a natural and serene getaway with all the comforts of home- a full kitchen (ie, all utensils, setting for four), a bathroom with shower and laundry, a queen bedroom, and a queen foldout sofa in the living room by the wood burning stove. The windows roll up from the outside and have permanent screens inside. There is also a BBQ grill, a separate firepit, and WiFi via satellite.

Aug. 14 – 21

$200 CAD per night

Guest favourite

Guesthouse in Boston

4.98 out of 5 average rating, 148 reviews

The Bunkhouse- simple & serene w/mountain views

Enjoy the solace and beauty of the Blue Ridge Mountains with modern and local comforts. Retreat and explore on this old 100acre farm- via foot- or float on the tiny pond in a kayak or SUP. Or venture out to Shenandoah National Park, the local coffee shops, eateries, wineries, and breweries. Whatever you choose the bunkhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

Sep. 13 – 20

$200 CAD per night

Guest favourite

Cottage in Sperryville

4.96 out of 5 average rating, 362 reviews

The River Cottage: Main Street Sperryville, VA

A Quaint private building, originally built as a Blacksmith Shop. Conestoga wagons were made behind this building near the Thornton River.; now guest will enjoy a recently renovated and spacious one room 'suite' right off of Main Street. Queen bed with plush bedding. Private bathroom with shower. Kitchenette with hotplate, smoothie maker, coffee maker, and microwave. Private deck that overlooks the Thornton River. Outdoor shower.

Sep. 17 – 24

$428 CAD per night

Guest favourite

Cabin in Luray

4.95 out of 5 average rating, 168 reviews

Dreamy Couples Cabin in the Shenandoah Forrest

A hidden gem by all means, The Madeline Cabin invites you in with the warmest regards. You'll be hosted by Ritter Stays, a young family-run company that believes in the magic of hospitality and what it can offer to those who are traveling. We hope that upon your stay you will be reconnected to nature and to the ones you came with. Simplistic, beautiful, and serene, your dreamy getaway awaits. We are so happy to host you.

Jan. 26 – Feb. 2

$216 CAD per night

Guest favourite

Tiny homes in Linville

4.99 out of 5 average rating, 601 reviews

The spring house at Thistle Hollow

Beautifully renovated spring house on the grounds of the 1800s Peter Breneman House. Soak up peace and quiet in one of the most beautiful corners of the Shenandoah Valley. Enjoy starry skies, sunrises, and birdwatching from your private porch. 9 minutes from Eastern Mennonite University, 13 minutes from James Madison University, and 45 minutes from the entrance to Shenandoah National Park.

Aug. 18 – 25

$171 CAD per night

Guest favourite

Farm stay in Sperryville

4.91 out of 5 average rating, 129 reviews

Carriage House @ Sharp Rock Winery and Old Rag Mtn

Join us at Sharp Rock Vineyards in our 1850 Carriage House, a cozy one room cottage perfect for a couple, set above a rushing trout stream at the base of Old Rag Mountain. Enjoy the peace of a private setting only minutes from Shenandoah National Park and hiking at Old Rag and White Oak Canyon. We are 10 minutes from Sperryville and close to local wineries, breweries, and eateries.

Dec. 25 – Jan. 1

$249 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Sperryville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Sperryville's top sights

Headmasters Pub23 locals recommend

Rappahannock Pizza Kitchen (RPK)41 locals recommend

Before & After24 locals recommend

Burgers N Things3 locals recommend

Copper Fox Distillery49 locals recommend

Thornton River Grille19 locals recommend

Other great vacation rentals in Sperryville

Guest favourite

Cabin in Lost River

4.96 out of 5 average rating, 112 reviews

Rustic and stylish mountain getaway

Apr. 15 – 22

$158 CAD per night

Guest favourite

Apartment in Culpeper

4.98 out of 5 average rating, 147 reviews

TreeTop at Mt Run Lake (Private Guest Apartment)

Mar. 14 – 21

$166 CAD per night

Guest favourite

Guest suite in Brandy Station

4.98 out of 5 average rating, 133 reviews

Studio apartment at historic Glenmore

Sep. 12 – 19

$131 CAD per night

Guest favourite

Guesthouse in Elkton

4.99 out of 5 average rating, 160 reviews

Noná’s Nest

Oct. 15 – 22

$140 CAD per night

Guest favourite

Guesthouse in Marshall

5.0 out of 5 average rating, 102 reviews

Moon Hold Cottage - Retreat, Refresh, Recharge

Aug. 1 – 8

$171 CAD per night

Guest favourite

Home in Culpeper

4.95 out of 5 average rating, 350 reviews

Charming Restored Farmhouse Minutes from Culpeper

Jan. 18 – 25

$241 CAD per night

Guest favourite

Home in Edinburg

4.98 out of 5 average rating, 353 reviews

Jay Birds Nest - Pet Friendly

Dec. 8 – 15

$166 CAD per night

Guest favourite

Guest suite in Syria

4.97 out of 5 average rating, 200 reviews

❤️Old Rag Mountain Views on 70 Acres near SNP!

Jul. 16 – 23

$204 CAD per night

Show all

Quick stats about vacation rentals in Sperryville

Total rentals
10 properties
Local attractions
Headmasters Pub, Rappahannock Pizza Kitchen (RPK), and Before & After
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
1.4K reviews
Nightly prices starting at
$246 CAD before taxes and fees

Vacation rentals in Sperryville

Top-rated vacation rentals in Sperryville

Tiny homes in Reva

Farm stay in Sperryville

Guesthouse in Flint Hill

Guesthouse in Syria

Home in Sperryville

Guest suite in Culpeper

Yurt in Etlan

Guesthouse in Boston

Cottage in Sperryville

Cabin in Luray

Tiny homes in Linville

Farm stay in Sperryville

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Sperryville vacation rentals

Stay near Sperryville's top sights

Other great vacation rentals in Sperryville

Cabin in Lost River

Apartment in Culpeper

Guest suite in Brandy Station

Guesthouse in Elkton

Guesthouse in Marshall

Home in Culpeper

Home in Edinburg

Guest suite in Syria

Quick stats about vacation rentals in Sperryville

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore