Best Vacation Homes in Ashland
House
10.0(62 Reviews)
2 Bedrooms
2 Baths
4 Guests
2200 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $211/Night
7 Nights - US $1,476
House
5 Bedrooms
5 Baths
15 Guests
5005.22 ft²
- Fireplace/Heating
- Parking
Internet
Child Friendly
US $714/Night
7 Nights - US $5,000
Hotel
9.4(674 Reviews)
1 Bath
- Fireplace/Heating
Pool- Balcony/Terrace
Breakfast
US $93/Night
7 Nights - US $653
House
10.0(26 Reviews)
2 Bedrooms
1 Bath
4 Guests
980 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $165/Night
7 Nights - US $1,156
House
1 Bedroom
3 Baths
8 Guests
1797.57 ft²
Hot Tub- Pet Friendly
- Parking
Air Conditioner
US $147/Night
7 Nights - US $1,027
House
9.8(97 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $141/Night
7 Nights - US $989
House
9.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
1345 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $134/Night
7 Nights - US $935
Condo
3 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $228/Night
7 Nights - US $1,595
Ashland Luxury Rentals
House
10.0(29 Reviews)
10 Bedrooms
8 Baths
20 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,070/Night
7 Nights - US $7,493
House
10.0(9 Reviews)
7 Bedrooms
3 Baths
17 Guests
4800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $963/Night
7 Nights - US $6,739
House
10.0(5 Reviews)
5 Bedrooms
4 Baths
15 Guests
5000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $688/Night
7 Nights - US $4,813
House
9.8(8 Reviews)
5 Bedrooms
3 Baths
9 Guests
2700 ft²
- Hot Tub
Spa- Fireplace/Heating
- Balcony/Terrace
US $470/Night
7 Nights - US $3,292
House
9.8(105 Reviews)
4 Bedrooms
3 Baths
12 Guests
3200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $432/Night
7 Nights - US $3,025
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $413/Night
7 Nights - US $2,893
House
8.4(19 Reviews)
4 Bedrooms
2 Baths
10 Guests
1200 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $340/Night
7 Nights - US $2,380
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
1750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $336/Night
7 Nights - US $2,355
Ashland Pet Friendly Vacation Rentals
House
2 Bedrooms
1 Bath
1 Guest
1005 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $162/Night
7 Nights - US $1,133
Hotel
8.4(182 Reviews)
6 Baths
303.18 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $98/Night
7 Nights - US $685
Apartment
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $160/Night
7 Nights - US $1,121
Hotel
8.0(241 Reviews)
1 Bath
333.68 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
US $75/Night
7 Nights - US $525
Apartment
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $143/Night
7 Nights - US $1,000
House
4 Bedrooms
3 Baths
16 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $256/Night
7 Nights - US $1,793
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $224/Night
7 Nights - US $1,565
House
9.6(29 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $202/Night
7 Nights - US $1,417
Ashland Large Vacation Homes
House
10.0(38 Reviews)
4 Bedrooms
2 Baths
10 Guests
1600 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $261/Night
7 Nights - US $1,825
House
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $400/Night
7 Nights - US $2,800
Cabin
10.0(50 Reviews)
4 Bedrooms
3 Baths
20 Guests
3000 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $185/Night
7 Nights - US $1,298
House
9.6(8 Reviews)
5 Bedrooms
1 Bath
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $359/Night
7 Nights - US $2,510
House
8.0(1 Review)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $424/Night
7 Nights - US $2,966
US $654/Night
7 Nights - US $4,577
House
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $653/Night
7 Nights - US $4,574
House
10.0(26 Reviews)
3 Bedrooms
1 Bath
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $238/Night
7 Nights - US $1,669
Why Choose Rent By Owner for your Ashland Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Ashland
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can significantly enhance your experience, as each season offers unique opportunities to enjoy the area's natural beauty and local events, making it essential to plan your trip according to the climate and activities available during your preferred travel period.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this time, the area experiences pleasant weather that is ideal for outdoor activities and exploring local scenery.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Fall (September to October)
The region offers beautiful autumn foliage, making it a popular time for experiencing natural beauty and outdoor events.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
With colder temperatures and fewer visitors, this season provides a peaceful retreat and a chance to enjoy cozy accommodations.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
Late Fall to Early Winter (November to December)
This period sees decreased tourist activity, offering quieter surroundings and more affordable rates for your stay here.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Ashland
How to Book Your Ashland Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Ashland
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or deck ideal for relaxing or dining al fresco amid scenic views.
- Take advantage of spacious yards or gardens perfect for outdoor activities and gatherings.
- Make use of community or shared outdoor pools, especially during warmer months in this charming region.
- Benefit from access to nearby hiking trails or nature walks that showcase the natural beauty of the area.
- Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
- Experience outdoor recreation options such as kayaking, fishing, or boating if located near water bodies.
- Find convenient parking with dedicated outdoor spaces to easily explore all that here has to offer.
Top Attractions Around Ashland
What attractions are nearby?
While visiting, you can enjoy a variety of outdoor activities and local attractions just moments from your accommodation in Ashland, Illinois, offering you an authentic experience of the region’s natural beauty and cultural charm.
Family Activities
- Deer Run School and Museum: Explore local history at this family-friendly site that offers engaging exhibits and interactive displays about the area's educational heritage.
- Lakeview Park: Enjoy a day outdoors with picnicking, playgrounds, and scenic walking paths that make it perfect for family outings in the region.
- Fishing at nearby lakes: Spend quality time together by casting lines at the tranquil lakes surrounding here, ideal for relaxing family fishing experiences.
- Community events and festivals: Participate in seasonal celebrations, fairs, or outdoor concerts hosted in the area, providing fun activities for all ages.
Adult Activities
- Wineries and Wine Tasting Tours: Explore the local vineyards with guided tastings that showcase the region's celebrated wine culture, perfect for a relaxing day in this charming area.
- Historic Downtown Strolls: Wander through the historic streets filled with boutique shops, cozy cafes, and unique art galleries, offering an authentic taste of community life here.
- Outdoor Recreation at State Parks: Engage in outdoor activities like hiking, picnicking, or birdwatching at nearby state parks that highlight the natural beauty of the region.
- Cultural Events and Festivals: Participate in local festivals and arts events often held throughout the year, giving you an immersive experience into the area's vibrant cultural scene.
Ashland Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Events and Activities: Check the area's community calendars to discover events and festivals that enhance your experience while staying in this charming destination.
- Choose the Right Vacation Rental Location: Select a property close to key attractions or scenic spots to maximize your time enjoying all that the region has to offer.
- Plan Outdoor Adventures: Take advantage of nearby parks and natural settings to engage in outdoor activities such as hiking, biking, or leisurely walks during your visit.
- Connect with Local Cuisine: Use your stay as an opportunity to sample regional flavors at local eateries or even arrange for a cooking experience at your vacation rental.
Transportation Options
- Car Rentals: You can easily rent a car in Ashland to explore the area's scenic routes and local attractions at your own pace.
- Public Transit: The regional bus services provide an economical way to get around, connecting you to nearby towns and amenities.
- Taxi Services: Taxis and ride-sharing options are readily available for convenient transportation within the destination and its surroundings.
- Bicycle Rentals: Biking is a popular choice here, with bike rentals offering an eco-friendly and flexible way to discover the region's beauty.
Local Customs Options
- Community Celebrations: Participating in local festivals and parades offers a glimpse into the area's rich cultural traditions during your stay.
- Food Traditions: Sampling regional specialties at community gatherings provides an authentic taste of the region's culinary heritage.
- Historic Respect: Visitors often observe respectful attitudes towards historic landmarks, reflecting the area's pride in its history.
- Local Etiquette: Engaging politely with residents and observing customary greetings ensures a warm and welcoming experience here.
Ashland Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Ashland?
There are a lot of options in Ashland. If you plan on staying in the Ashland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Ashland:
- 3 BR, w/garage &1BR set up as home office w/printer
- Family friendly home off bike trail and quiet subdivision with lots of updates!
- Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg
- Pet friendly remodeled bungalow home just two blocks from Washington Park.
- Holly & Matt Suite @ Three Pines Petersburg
- The Hidden Gem- Superb 7-bedroom Studio with arcade, theater and more!
- Great for Groups: Home 3 Mi to Dtwn Springfield!
- 7 Min to Scheels Sports Complex Sleeps 5 Projector Bunk Bed
- Top-Rated Premier 3-Bedroom Spotless & Charming Home
- Hay Rake Country Acres-Peaceful Getaway - 4BR, 2BA - Sleeps 8
2. How many vacation rentals have private pools in Ashland?
There are 2 vacation rentals with private pools near Ashland. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Ashland are best for families?
If you are looking for a family-friendly vacation home in Ashland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Ashland:
4. How many Rentbyowner vacation rentals are available in Ashland?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 84 in the Ashland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Ashland.
5. What is the cancellation policy for vacation rentals in Ashland, Illinois?
Cancellation policies vary by listing. To understand the specific terms, please review the cancellation details listed on the property page or contact the property owner directly before booking.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, service fees, or local taxes are typically included in the listing details. Be sure to read the full description and fee breakdown to ensure transparency before completing your reservation.
7. How do I ensure my booking is secure and reliable for this destination?
Bookings are secured through a trusted platform that verifies listings and hosts. Confirm the listing's reviews and ratings, and communicate through the platform to maintain a safe transaction process.
8. What amenities are commonly available in vacation rentals in the region?
Most properties offer essential amenities like Wi-Fi, parking, and kitchen facilities. For specific amenities, check the detailed listing or contact the property owner to confirm what’s included during your stay.
9. What is the best way to get assistance if I encounter issues during my stay?
For support, contact the property owner directly through the messaging system provided. If urgent, the platform offers customer support to help resolve any problems efficiently while you are in this area.
Ashland Top Rated Vacation Rentals
US $125/Night
7 Nights - US $875
US $124/Night
7 Nights - US $870
Hotel
8.7(45 Reviews)
3 Baths
283.45 ft²
- Private Pool
Oceanfront- Fireplace/Heating
- Pool
US $130/Night
7 Nights - US $908
US $85/Night
7 Nights - US $598
Hotel
8.0(1005 Reviews)
1 Bath
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $78/Night
7 Nights - US $543
Hotel
7.9(103 Reviews)
1 Bath
495.14 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Parking
US $98/Night
7 Nights - US $685
Hotel
7.8(494 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $83/Night
7 Nights - US $582
Hotel
7.8(454 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $103/Night
7 Nights - US $722
