Vacation rentals in Ashland

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Ashland

  • Total vacation rentals

    Explore 20 vacation rentals in Ashland

  • Nightly prices starting at

    Ashland vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 1,550 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Ashland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Ashland rentals

Top-rated vacation rentals in Ashland

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

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Top guest favorite
A welcoming entrance is framed by brick arches and wooden stairs leading to the upper level. The pathway is lined with gravel and vibrant greenery, including flowering plants, creating an inviting approach to the private entrance.
Guest suite in Glen Allen
4.97 out of 5 average rating, 182 reviews

The BeeHive

Kick back and relax in this calm, stylish space. Private, modern studio suite on the first floor of a single family home in Glen Allen, Virginia. The home is located in a quiet, friendly suburban neighborhood that is close to both Short Pump and downtown Richmond. Just 20 minutes away from downtown Richmond and an even closer 10 minutes to Short Pump, both packed with restaurants, shops, and other attractions. Wooded area behind the home has a hiking path to the Echo Lake Park for nature lovers.

Top guest favorite
The townhouse apartment features a charming exterior with a light grey siding and white trim. A set of stairs leads to the entrance, framed by two flags. Lush green grass and trees surround the property, enhancing the welcoming presence of the home.
Apartment in Hanover
5 out of 5 average rating, 147 reviews

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

Guest favorite
Home in Ashland
4.93 out of 5 average rating, 137 reviews

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!

Top guest favorite
A paved driveway lined with trees leads towards a country guest house, offering a serene path. Inside, a spacious bed is paired with contemporary nightstands and lamps. A private pool shines under clear skies, featuring a neatly manicured surrounding area and lounge chairs for relaxation.
Guesthouse in Glen Allen
4.86 out of 5 average rating, 646 reviews

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.

Top guest favorite
Apartment in Richmond
4.99 out of 5 average rating, 102 reviews

Peaceful, private, upscale apartment near U of R

1 mile from UofR & a 2 min. walk to Three Chopt & Patterson Publix/restaurants, you’ll find a home-away-from-home in this impeccable 700sf one-bedroom apt. The private tree-house-like space includes large comfy couch, queen bed, full kitchen (granite, stainless), washer-dryer, fast wifi, & 2 smart TVs. The apt is above a detached garage not used for cars, which ensures quiet/privacy + off-street parallel parking (in front of them in the alley). Access does require climbing exterior stairs.

Top guest favorite
Guesthouse in Richmond
4.99 out of 5 average rating, 155 reviews

Spacious, pet-friendly nature retreat | The Bohive

Escape to The Bohive off I-95, a charming 1200 sq ft studio, conveniently located just off the interstate & minutes from downtown. On a private “nature reserve”, this is the perfect place to unwind & recharge. Inside, you'll find a comfortable king bed & kitchenette (no stove). The cozy living area has a smart TV, great for relaxing after a long day of exploring. Enjoy coffee on the private deck or immerse yourself in nature before heading out. Great spot for road trippers! STR2024-00002

Guest favorite
The living area features a spacious sectional sofa, complemented by a coffee table and decorative accents. A fireplace serves as a focal point, while large windows allow natural light to enhance the neutral tones of the room. An open layout connects to the kitchen and dining space.
Home in Ashland
4.94 out of 5 average rating, 172 reviews

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.

Top guest favorite
A spacious front yard is presented, featuring a well-maintained lawn that extends towards a charming two-story home. The house includes a welcoming porch and a staircase leading to the upper level, surrounded by a variety of greenery and flowering plants.
Apartment in Rockville
4.97 out of 5 average rating, 355 reviews

The Home Stretch

Welcome to "The Home Stretch", a beautiful quiet place in the country just a few miles from Short Pump (which has great restaurants, Golf Courses, Drive Shack, wineries, Breweries. Our second floor apartment features a private entrance with all the things you may need while you are away from home. It has a spacious living area, eat in kitchen, queen bed and 2 trundle-like twin beds. We are on the premises but not in your space at all. Available day and night should you need anything.

Top guest favorite
A welcoming living room is adorned with blue and white striped walls, showcasing a blend of modern and bohemian styles. The seating includes a leather sofa and a unique armchair, complemented by a natural wood coffee table. A fireplace and entertainment unit provide additional features.
Home in Ashland
4.97 out of 5 average rating, 99 reviews

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.

Top guest favorite
An exterior view showcases a wooden staircase leading to the entrance of the accommodation. The stairs are surrounded by trees, with a pathway made of stone tiles visible in the foreground. The rustic brick wall of the building adds character to the serene natural setting.
Apartment in Ashland
4.97 out of 5 average rating, 151 reviews

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.

Top guest favorite
Cottage in Ashland
4.81 out of 5 average rating, 81 reviews

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.

Top guest favorite
The kitchen area features wooden cabinetry and a spacious white refrigerator. A dining table with four wooden chairs is set to one side, while the living area, equipped with a cozy blue couch, is visible in the background. Natural light illuminates the space.
Guesthouse in Ashland
4.96 out of 5 average rating, 672 reviews

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!

Popular amenities for Ashland vacation rentals

When is the best time to visit Ashland?

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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.