Waynesboro holiday lettings

We found 967 holiday rentals — enter your dates for availability
Discover a selection of 29 homes and other holiday rentals in Waynesboro that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for hanging out with the people that matter most, including parking and a TV. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Waynesboro

Showing deals for:27 Nov - 4 Dec

Exterior
Living area
Dining
Private kitchen
Exceptional
(5 reviews)

Majestic Mtn Cabin w quick hiking & overlook access

Nellysford

8% off
£2,052
for 7 nights, 1 chalet
£293 per night
includes taxes & fees
Majestic Mtn Cabin w quick hiking & overlook access
Interior
Spectacular Mountain Views from your private deck in Wintergreen!
Living area
Exterior
Exceptional
(11 reviews)

Wren Time, Wintergreen Mountain Retreat with Hot Tub

Nellysford

7% off
£2,718
for 7 nights, 1 cabin
£388 per night
includes taxes & fees
Wren Time, Wintergreen Mountain Retreat with Hot Tub
Front of House
58" flat screen, basic cable. Living Room
Dining Room Table
Master Bedroom, King Bed, private bathroom
Exceptional
(111 reviews)

Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck

Nellysford

11% off
£1,476
for 7 nights, 1 home
£211 per night
includes taxes & fees
Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck
Private well-lit walkway to your private entrance on home's main floor.
Wall-to-wall windows creating a backdrop of treetops & mountain views.
Living room with full views of valley & mountains. Wood burning fireplace.
Main living floor contains dining, kitchen, living room, and half bath.
Exceptional
(56 reviews)

Spacious + Serene Mtn Top Escape, 4 En Suites

Nellysford

8% off
£2,227
for 7 nights, 1 home
£318 per night
includes taxes & fees
Spacious + Serene Mtn Top Escape, 4 En Suites
Fully Equiped Kitchen
Living area
Living area
Outside your Condo
Exceptional
(129 reviews)

Eagles Court Slopeside Condo, Wifi, Walk to everything!

Nellysford

11% off
£1,144
for 7 nights, 1 apartment
£163 per night
includes taxes & fees
Eagles Court Slopeside Condo, Wifi, Walk to everything!
Dining
Living area
Private kitchen
Living area
Exceptional
(22 reviews)

Above the Clouds! Perfect Escape for Families!

Nellysford

12% off
£2,322
for 7 nights, 1 home
£332 per night
includes taxes & fees
Above the Clouds! Perfect Escape for Families!
Private kitchen
Private kitchen
Exterior detail
Interior
Exceptional
(61 reviews)

Rockfish Farmhouse - Home In the heart of The Rockfish Valley

Afton

8% off
£1,928
for 7 nights, 1 home
£275 per night
includes taxes & fees
Rockfish Farmhouse - Home In the heart of The Rockfish Valley
Living area
Dining
Living area
Interior
Exceptional
(59 reviews)

Spectacular mountain home perfect for multiple families! Just added deck firepit

Nellysford

7% off
£1,720
for 7 nights, 1 home
£246 per night
includes taxes & fees
Spectacular mountain home perfect for multiple families! Just added deck firepit
Property grounds
Outdoor spa tub
Property grounds
Private kitchen
Exceptional
(111 reviews)

Remodeled 3BR/2BA Ski Chalet off Tyro Slope

Nellysford

7% off
£1,343
for 7 nights, 1 home
£192 per night
includes taxes & fees
Remodeled 3BR/2BA Ski Chalet off Tyro Slope
Private kitchen
Interior
Interior
Room
Exceptional
(9 reviews)

Inn at the Woods: Updated Cabin w/Mountain Views

Afton

7% off
£2,007
for 7 nights, 1 cabin
£287 per night
includes taxes & fees
Inn at the Woods: Updated Cabin w/Mountain Views
Interior
Exterior
Fire pit with accessories to use as grill
Private kitchen
Exceptional
(70 reviews)

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Montebello

12% off
£848
for 7 nights, 1 cabin
£121 per night
includes taxes & fees
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Dining area and kitchen.
Enjoy the hot tub under the string lights in the evenings.
10 minute walk to the lodge, lifts and dining (2 min drive)
Main upstairs living area (wide screen lens was used to show entire space)
Exceptional
(6 reviews)

Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

Nellysford

7% off
£1,531
for 7 nights, 1 home
£219 per night
includes taxes & fees
Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard
kitchen
Property grounds
wintergreen cottage...ski slope is to the lower right of photo
master bedroom
Exceptional
(94 reviews)

COZY SKI COTTAGE--SKI IN SKI OUT

Nellysford

7% off
£1,734
for 7 nights, 1 home
£248 per night
includes taxes & fees
COZY SKI COTTAGE--SKI IN SKI OUT
The downstairs full bathroom with shower/tub combo and washer/dryer.
The propane fire pit provides intimacy and warmth!
Our private home.
The first bedroom on the bottom floor.
Exceptional
(25 reviews)

Secluded 20+ Acre Retreat Near Brew & Wine Trails

Afton

7% off
£1,777
for 7 nights, 1 home
£254 per night
includes taxes & fees
Secluded 20+ Acre Retreat Near Brew & Wine Trails
Living area
Living area
Dining
Living area
Exceptional
(28 reviews)

Condo at Fairway Woods, perfect home base for ski season! ☃️🏂

Nellysford

12% off
£1,563
for 7 nights, 1 home
£223 per night
includes taxes & fees
Condo at Fairway Woods, perfect home base for ski season! ☃️🏂
HOA is great at clearing the walkway and parking lot when it snows.
Relax and recharge at Positive Altitude!
Comfy living room with wood burning fire, smart TV and sound bar to stream tunes
Wonderful space to connect with friends and family!
Exceptional
(19 reviews)

Enjoy all 4 seasons at this spacious, pet friendly home! Great views, sleeps 10

Nellysford

7% off
£2,518
for 7 nights, 1 home
£360 per night
includes taxes & fees
Enjoy all 4 seasons at this spacious, pet friendly home! Great views, sleeps 10
Interior
Terrace/patio
Dining
Private kitchen
Exceptional
(6 reviews)

Spacious Estate on 6 acres, King Suite + Efficiency convenient to I-64 in Crozet

Charlottesville

16% off
£2,214
for 7 nights, 1 home
£316 per night
includes taxes & fees
Spacious Estate on 6 acres, King Suite + Efficiency convenient to I-64 in Crozet
Kitchen
Living room
Unit from entrance
Cliffs
Exceptional
(57 reviews)

Best view in Wintergreen! Large, comfortable 3 bedroom, 3 bath condo.

Nellysford

8% off
£2,027
for 7 nights, 1 apartment
£290 per night
includes taxes & fees
Best view in Wintergreen! Large, comfortable 3 bedroom, 3 bath condo.
Interior
Exterior
Property grounds
Interior
Exceptional
(29 reviews)

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

Montebello

12% off
£848
for 7 nights, 1 cabin
£121 per night
includes taxes & fees
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
Interior
Exterior
Interior
Private kitchen
Exceptional
(23 reviews)

New Blue RIdge Mountains Montebello, Virginia with stary stary skies

Montebello

12% off
£848
for 7 nights, 1 cabin
£121 per night
includes taxes & fees
New Blue RIdge Mountains Montebello, Virginia with stary stary skies
Exterior
Living area
Interior
Private kitchen
Exceptional
(5 reviews)

6BR: Every Room Has Private Bath + Mountain Views 2 Decks

Nellysford

8% off
£6,026
for 7 nights, 1 home
£861 per night
includes taxes & fees
6BR: Every Room Has Private Bath + Mountain Views 2 Decks
Master bedroom TV and chest of drawers
Private kitchen
Living area
Morning coffee from Keurig on the deck!
Exceptional
(91 reviews)

Location, location, location mountain side in Wintergreen Mountain Village

Nellysford

11% off
£1,052
for 7 nights, 1 apartment
£150 per night
includes taxes & fees
Location, location, location mountain side in Wintergreen Mountain Village
Living area
Great mountain views, with relaxing pond.
Private kitchen
Room
Exceptional
(65 reviews)

Suite in Shenandoah Valley

Waynesboro

6% off
£1,011
for 7 nights, 1 home
£144 per night
includes taxes & fees
Suite in Shenandoah Valley
Front of Condo Building
Property grounds
Stoney Creek Golf Course open year round!
Interior
Exceptional
(150 reviews)

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

Nellysford

8% off
£991
for 7 nights, 1 apartment
£142 per night
includes taxes & fees
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Head to the scenic city of Waynesboro

Come and experience Waynesboro and its wineries, festivals and art galleries. Travellers especially like the hiking, restaurants and skyscrapers in this scenic and cosmopolitan city. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Waynesboro

Are you searching for things to do in the city? Venture out of your cosy holiday rental and check out everything that makes Waynesboro a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Veritas Vineyard and Winery (4.5 mi / 7.3 km)
  • Afton Mountain Vineyards (4.7 mi / 7.5 km)
  • King Family Vineyards (8.8 mi / 14.1 km)
  • Wintergreen Resort (10.7 mi / 17.3 km)
  • Pippin Hill Farm & Vineyards (14.5 mi / 23.3 km)
  • Cross Keys Vineyards (17.7 mi / 28.5 km)

Exploring the natural features in Waynesboro

Whether you're an active traveller or just want to appreciate the scenery, Waynesboro is a great spot to appreciate mother nature. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Rockfish Gap Entrance Shenandoah (2.8 mi / 4.5 km)
  • Blue Ridge Parkway North Entrance (3.2 mi / 5.1 km)
  • Sherando Lake Recreation Area (12.2 mi / 19.7 km)
  • Crabtree Falls (18.2 mi / 29.4 km)
  • Natural Chimneys (22.5 mi / 36.2 km)
  • George Washington National Forest (25.6 mi / 41.2 km)

Transport to and around Waynesboro

The nearest airport is in Weyers Cave, VA (SHD-Shenandoah Valley Regional), located 13.5 mi (21.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Charlottesville, VA (CHO-Charlottesville-Albemarle), which is 24.7 mi (39.7 km) away.

Frequently asked questions

What is the best area to stay in Waynesboro when booking a holiday rental?
When considering a holiday rental in Waynesboro, Virginia, the downtown area emerges as an excellent choice. This vibrant neighbourhood offers a charming blend of local culture, dining, and easy access to the scenic beauty of the surrounding region. With a variety of properties available, from quaint cottages to modern apartments, visitors can find accommodation that suits their preferences and budget.One of the highlights of staying in downtown Waynesboro is the proximity to the historic Waynesboro Downtown Historic District, where you can explore unique shops and enjoy delightful eateries. Additionally, the nearby Shenandoah Valley Art Centre provides a glimpse into the local art scene, featuring exhibits from talented regional artists.Another appealing area to consider is the vicinity of the Blue Ridge Parkway. Known for its breathtaking views and outdoor activities, this region is great for nature enthusiasts. You can easily access hiking trails and picnic spots, making it an ideal base for those looking to immerse themselves in the stunning landscapes of the Blue Ridge Mountains.
How much does it cost to rent a holiday home in Waynesboro?
Prices for holiday rentals in Waynesboro vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Waynesboro to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Waynesboro holiday house rentals?
You can find great discounts on house rentals in Waynesboro on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Waynesboro ski resort rentals?
For ski resort rentals near Waynesboro, Virginia, the closest ski area is Wintergreen Resort, which is just a short drive away. Visitors looking for accommodation should consider the surrounding areas of Nellysford and the Wintergreen community itself. At Wintergreen Resort, you'll find various lodgings, including comfortable condos and spacious lodges that cater to families and groups. Many of these properties offer amenities such as fully equipped kitchens, fireplaces, and easy access to the ski slopes, making them great for those wanting a convenient ski getaway.In Nellysford, you can discover charming cabins and mountain lodges, often located among the trees and providing a more secluded experience. These rentals typically feature modern comforts, including hot tubs, outdoor decks, and scenic views, ideal for unwinding after a day on the slopes. Furthermore, Nellysford offers proximity to local wineries and hiking trails, enhancing the overall experience for visitors.For those keen on exploring beyond skiing, the area boasts numerous outdoor activities, including hiking and mountain biking in the warmer months, with trails that offer stunning vistas of the Blue Ridge Mountains.
What is the most popular type of holiday rental accomodation in Waynesboro?
In Waynesboro, holiday houses are the most prevalent type of holiday rental, with around 72 available in various neighbourhoods throughout the area. These houses typically offer spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas such as gardens or patios, making them ideal for families or groups looking for comfort and convenience. Additionally, there are about 30 apartments scattered across the town, providing a more compact and convenient option for couples or solo travellers. Many of these apartments come with essential amenities like kitchen facilities and a cosy living space. For those seeking a more rustic experience, there are several cabins available, which often feature unique designs and natural surroundings, superb for immersing oneself in the scenic beauty of the Virginia countryside.
Are there any family house rentals in Waynesboro?
In Waynesboro, Virginia, there are numerous family-friendly house rentals available—specifically, around 23 options throughout the area. This charming city is a great base for families, offering spacious rooms that typically include multiple bedrooms, full kitchens for preparing family meals, and comfortable living areas for relaxation. Many properties may also feature outdoor spaces where children can play and adults can unwind after a busy day.The locale is close to the beautiful Blue Ridge Mountains, making it superb for outdoor enthusiasts who enjoy hiking, biking, and exploring nature. Additionally, visitors can easily access local attractions such as the Waynesboro Heritage Museum and the picturesque Fishburne Park, which offers playgrounds and picnic spots for a family outing.
Can I rent a holiday home with a pool or hot tub in Waynesboro?
In Waynesboro, there are several holiday homes available for rent that feature pools or hot tubs, providing a refreshing option for travellers looking to relax. The city is located in the beautiful Shenandoah Valley, where visitors can enjoy stunning mountain views and access to outdoor activities.Many properties in this area come equipped with amenities such as private pools, hot tubs, spacious outdoor decks, and fully stocked kitchens, making them ideal for families or groups looking to unwind after a day of exploring. Additionally, you may find some rentals with landscaped gardens, barbecue facilities, and comfortable seating areas for alfresco dining.
Can I find long-stay holiday rentals in Waynesboro?
A long-stay holiday rental in Waynesboro is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Waynesboro?
In Waynesboro, there are several pet-friendly house rentals available, with around 17 options to choose from. These accommodations typically feature amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them suitable for families and groups travelling with pets. Many properties offer outdoor spaces where pets can enjoy fresh air, and some even include features like fenced yards for added safety.The area is surrounded by natural beauty, with nearby parks such as the Waynesboro City Park, which provides walking trails and open spaces for pets to explore. Additionally, the Blue Ridge Parkway is not far away, offering breathtaking views and ample opportunities for hiking with your furry companions.
Are there any remote work holiday rentals in Waynesboro?
In Waynesboro, Virginia, there are numerous remote work holiday rentals available, with approximately 99 options to choose from. This charming city is well-suited for those looking to blend work and leisure, offering properties equipped with essential amenities for remote working, such as free Wi-Fi and designated workspaces with desk chairs. Many rentals also provide comfortable living areas, allowing guests to unwind after a productive day.The area is rich in natural beauty, with proximity to the stunning Blue Ridge Parkway and the picturesque Shenandoah National Park, making it an ideal location for those who enjoy outdoor activities during their downtime. Additionally, Waynesboro boasts a vibrant local scene with shops, restaurants, and cultural attractions, ensuring that visitors have plenty of options to explore when they step away from their work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Waynesboro holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Waynesboro with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Waynesboro?
In Waynesboro, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals, and decks or patios where travellers can enjoy the outdoors. Many rentals also feature onsite parking for convenience, ensuring that guests can easily access their vehicles. Additional amenities often include coffee and tea makers for a comforting start to the day.
When is the best time to visit Waynesboro for a holiday rental?
July is the most popular time to visit Waynesboro, Virginia, as the peak season runs from July to September. This vibrant period attracts holidaymakers looking to immerse themselves in the stunning natural beauty of the Shenandoah Valley. With warm temperatures ranging from the mid-teens to high 20s Celsius, it's an ideal time for outdoor activities such as hiking in the nearby George Washington National Forest or enjoying leisurely strolls through the picturesque downtown area.During July, visitors can partake in local events and festivals, adding to the lively option and making it a great month for travellers. The pleasant weather allows for comfortable exploration of the numerous trails and scenic viewpoints that define this region.If you're looking for a more budget-friendly option, consider visiting in December. While it's the low season, this month offers a unique charm with fewer crowds, and you can enjoy peaceful walks amid the winter landscapes. The festive holiday decorations in town create a warm and welcoming ambiance, great for a cozy getaway.
How early should I book a Waynesboro holiday rental?
Book your Waynesboro holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Waynesboro?
In Waynesboro, visitors can enjoy a variety of attractions that highlight the area's natural beauty and historical significance. The Blue Ridge Parkway is a major draw, offering breathtaking views and numerous opportunities for hiking and picnicking. The nearby Shenandoah National Park is another popular destination, featuring scenic drives and trails that appeal to outdoor enthusiasts.In the downtown area, the Wayne Theatre presents a range of performances and events, showcasing local talent and arts. Additionally, the Ridgeview Park provides a lovely setting for leisurely walks, picnics, and family-friendly activities, with its playgrounds and sports facilities.For history buffs, the Waynesboro Heritage Museum offers insights into the city's past, while the nearby historical sites such as the Battle of Waynesboro battlefield commemorate the Civil War era.
Can I change or cancel my Waynesboro home rental booking on Vrbo?
To find Waynesboro holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Waynesboro holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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