
Holiday houses in Ashland
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Ashland

Total holiday rentals
Explore 20 holiday rentals in Ashland

Nightly prices starting at
Ashland holiday rentals start at $70 AUD per night before taxes and fees

Verified guest reviews
Over 1,550 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Ashland holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Ashland rentals
Top-rated holiday rentals in Ashland
Guests agree: these stays are highly rated for location, cleanliness and more.

Apartment for 4 close to Ashland, RIR & The Meadow
This is a townhouse apartment located almost directly across the road from the historic Hanover Courthouse, and just a short walk from the historic Hanover Tavern. There are two bedrooms with queen beds, and one bathroom, all upstairs. Parking is free and directly in front of the apartment. There is one Smart TV with DISH network, Netflix, and Peacock streaming. WiFi is also included. There is a fully equipped kitchen and a coffee bar with a Keurig coffee pot. No smoking or vaping is allowed
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Charming 3-Bedroom Home in the Heart of Ashland
Ashland’s Whistle Stop – In the heart of the Center Of The Universe. Come & enjoy this beautifully remodeled & quaintly decorated 3-bedroom 2.5-bathroom home that will enfold you in the look & feel of the Town of Ashland. Come & enjoy the custom décor that celebrates all that Ashland has to offer, such as the Train Room, the Randolph Macon inspired bedroom, the Center of the Universe Billiards Room. This home has everything you will need or want to unwind for a weekend away or an extended stay!
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Private and Quiet Pool House Convenient Location
Pool is open for the season, it’s a private pool dedicated to our Airbnb guests only. This country guest house is very clean with a simple design. It's conveniently located seven miles away from Short Pump where you can enjoy dining, shopping, and entertainment. You will experience a quite relaxing retreat without leaving the city. We provide 4G wireless hotspot internet and a comfortable computer working space for business travelers. Grocery stores, business center, and banks are nearby.
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Luminous Architectural Gem
This luxurious space is filled with natural light streaming through the large windows. Exposed beams create a warm atmosphere. The open plan layout maximizes functionality, featuring a sleek modern kitchenette, a comfortable king size bed, and a stylish living area with a plush sofa and smart TV. The bathroom is crisp and contemporary with premium fixtures. Perfect for solo travelers or couples, the bright, beam-accented retreat offers a blend of comfort and character in an intimate setting.
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Glen Allen Mid-Century Modern Casita
Welcome to the Mid-Century Modern Casita located on the border of Henrico County and Richmond City; Situated in a safe and welcoming neighborhood with easy access to the best Richmond has to offer. Every detail has been carefully considered. This home is fully equip with a washer/dryer, cookware, fast internet, smart TVs, river towels and much more to make for an accommodating stay. Conveniently located to Virginia's top attractions, we are the perfect stopping ground for your next trip!
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Clean & Cozy getaway close to Kings Dominion & RMC
Clean & Cozy 3 bedroom, 2 full bath, located in Ashland, Va. Fully fenced in back yard, Board games & kid books for family time. YMCA, library & parks with in walking distance.1.3 miles from Randolph Macom College, 9 miles from King dominion,14 miles to Richmond Raceway, multiple restaurants, coffee shops & stores with-in 3 miles. Peaceful, cozy & quiet neighborhood. Absolutely NO PARTIES, NO "gatherings" NO Smoking, Any evidence of smoking inside will result in an additional $300 fee.
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For Art Sake - Colorful Cape
This unique place has a style all its own. Located in the quaint town of Ashland, our house backs up to Randolph Macon College. This house is walking distance to the college, restaurants and night life, library, Amtrak station, post office and many more amenities. Our cape has a clean, crisp bohemian/modern vibe filled with artwork, that will ensure you that you are away on a relaxing vacation. The yard is fully fenced with outdoor dining and grilling and is pet friendly.
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Ashland Aerie
Relax in this peaceful, stylish space for one, located north of Richmond. Park in the carport and go upstairs (21 steps) to enjoy privacy, convenience, and safety - with kitchenette, small washer/dryer, smart TV, desk, and exterior cameras. Ashland, less than three miles south, has restaurants (many), grocery stores, laundromats, a movie theater, a public library, churches, a post office, and Randolph Macon College. King’s Dominion and Meadow Event Park are six miles north.
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Charming Carriage House Historic Ashland
Charming, renovated carriage house privately located behind my Victorian home in the heart of Ashland's Historic District. Just two blocks from the center of town and the railroad station. Ashland has many restaurants, breweries, shops , a theater and activities at Randolph Macon College. Historic Richmond is less than 30 minutes away, the mountains and beach and Washington DC less than 2 hours away by car. The area is very bike friendly and wonderful for walkers.
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2 Bdrms★Pet Friendly★4K Theater★Fire Pit★Fast Wifi
Minutes from I-95 "The Cottage" is a great stop along your journey just 15 minutes to Kings Dominion or Meadow Event Park. Surf high speed internet, catch up on laundry, dine in Ashland or have a cookout and share stories around the campfire. You’ll love the Cottage because of the clean accommodations, complete kitchen, quiet neighborhood, home theater, comfy beds & pet friendly! The Cottage is great for Families, Couples, Business Travelers & Fun Seekers!
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The Duncan: Eco-luxury | Walk to RMC & Downtown
Unwind in our Federalist retreat with authentic MCM furnishings and global art. The Duncan is walkable to Amtrak, RMC, and downtown. Designed for sustainability and comfort with organic cotton linens, down bedding, and wool rugs. Enjoy a dedicated office, private gym, and large landscaped yard. Relax with coffee on the screened porch, a Solo Stove in the half-acre native garden, or stroll to nearby shops.
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Doswell Comfort
Relax from your travels in a cozy country home. Have morning coffee/tea on the porch onto the large yard & breezy tree lines. Close to local attractions; suitable for all families (pet friendly). Kings Dominion - 2 miles State Fairgrounds - 3.5 miles Randolph-Macon University - 7 miles Town of Ashland - 7 miles City of Richmond - 25 miles Central to multiple locations in Historic Hanover.
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Popular amenities for Ashland holiday rentals
Other great holiday rentals in Ashland

Peaceful 10-Acre Retreat | Pet-Friendly + Fire Pit
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The Cove | Fresh | Modern | 3BR | By Highways
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Peaceful 3 BR Ranch | King Bed | Fireplace
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Modern Glen Allen Home w/Game Room & Screened deck
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Luxurious Spacious Retreat Close to Everything
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The Safari House: Where Adventure & Comfort Awaits
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Lake/retreat shortpump Richmond Castlewood Estate
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Waterfront Escape | Hot Tub, Canoe & SUP
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When is the best time to visit Ashland?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $139 AUD | $139 AUD | $174 AUD | $192 AUD | $181 AUD | $180 AUD | $160 AUD | $160 AUD | $160 AUD | $160 AUD | $167 AUD | $163 AUD |
| Avg. temp | 4°C | 5°C | 9°C | 15°C | 19°C | 24°C | 26°C | 25°C | 22°C | 16°C | 10°C | 5°C |
Frequently Asked Questions
What are the best places to stay in Ashland?
Consider staying near downtown Ashland for easy access to shops, dining, and local attractions. The surrounding neighborhoods often have charming vacation rentals suited for various group sizes.
What are the best things to do in Ashland with kids?
Children often enjoy watching trains in the heart of town, visiting community parks, and exploring interactive exhibits at the Ashland Museum. Seasonal fairs and markets bring family-friendly entertainment throughout the year.
What are some of the best things to do in Ashland?
Ashland has walking tours along the train tracks, art galleries, and locally owned shops and eateries. Many guests enjoy community parks and cultural exhibits throughout the year.
How is the weather in Ashland?
Ashland has cool winters around 29–48°F (-2–9°C) and warm, humid summers near 69–90°F (21–32°C). Spring and fall are mild, with blooming trees and comfortable afternoons.
When is the best time to visit Ashland?
Spring and fall are often recommended for mild weather and colorful scenery. Summer welcomes outdoor festivities, while winter sees cozy events and local holiday traditions.
What are the best places to visit in Ashland?
Explore Ashland's historic Main Street, visit the Ashland Museum, and enjoy artwork at local galleries. The area has green spaces, seasonal markets, and classic train-themed attractions for a unique experience.
What are some hiking trails in Ashland?
Ashland has paved and natural walking trails in its parks and green spaces. For a longer hike, nearby nature preserves and wooded areas invite exploration through forested paths.
What are some family activities we can do in Ashland?
Families can explore playgrounds, watch trains roll through the center of town, and learn at the Ashland Museum. Seasonal events, outdoor concerts, and local ice cream shops are frequently suggested.
What are some of the best day trip ideas from Ashland?
Ashland is near historic sites, riverfront areas, and botanical gardens often recommended for day trips. Wineries, cultural centers, and outdoor recreation spots add variety for those looking to explore beyond town.
Are there any pet friendly accommodations available in Ashland?
Many vacation rentals in Ashland welcome pets, especially around downtown and residential areas. Parks and walking trails make it easy to enjoy time outside with your dog.
What are some local tips for visiting Ashland?
Enjoy train-watching from downtown benches, check out seasonal markets, and follow mural walks for hidden artwork. Locals suggest bringing comfortable footwear and sampling regional specialties.
What is Ashland known for?
Ashland is known for its historic railroad heritage, locally rooted arts scene, and welcoming community atmosphere. The town has lively festivals and preserved landmarks reflecting its cultural history.
What are the best hidden gems to explore in Ashland?
Explore local art studios, historic railroad sites, and tucked-away cafés near Main Street. Community gardens and mural walks provide creative touches often favored by visitors.
What are the best foods to try in Ashland?
Sample locally roasted coffee, Southern-inspired comfort dishes, and homemade desserts from neighborhood bakeries. Farm-fresh produce and small-batch treats are frequently suggested by residents.
What should I bring for a trip to Ashland?
Pack comfortable walking shoes, clothing for variable temperatures, and a light rain jacket. A camera and reusable water bottle are handy for exploring local sights and parks.
What is the nightlife in Ashland like?
Nightlife in Ashland has relaxed restaurants, casual bars, and occasional live music performances. Community gatherings and evening events are often hosted in local venues, creating a friendly atmosphere.
What are the most popular events or festivals in Ashland?
Ashland hosts train-themed events, art festivals, and markets throughout the year, with seasonal celebrations often held in late spring and around the holidays. Outdoor concerts and community fairs are popular traditions.
Are there family friendly vacation rentals in Ashland?
Many vacation rentals in Ashland are family friendly, especially those located near parks and downtown. Spacious layouts, welcoming hosts, and easy access to attractions are common features.
Destinations to explore
- New York Holiday rentals
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- Myrtle Beach Holiday rentals
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- North Myrtle Beach Holiday rentals
- Virginia Beach Holiday rentals
- Raleigh Holiday rentals
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- Wilmington Holiday rentals
- Kings Dominion
- Lake Anna State Park
- Pocahontas State Park
- Greater Richmond Convention Center
- Brown's Island
- The National
- Forest Hill Park
- Libby Hill Park
- Virginia Holocaust Museum
- Ingleside Vineyards
- The Poe Museum
- Altria Theater
- Science Museum of Virginia
- Children's Museum of Richmond
- Fredericksburg Battlefield Visitors Center
- James Madison's Montpelier
- Virginia State Capitol-Northwest
- American Civil War Museum
- Jefferson Park
- Metro Richmond Zoo
- General's Ridge Vineyard
- Hollywood Cemetery





