Best Vacation Homes in Ashland
House
10.0(49 Reviews)
3 Bedrooms
1 Bath
6 Guests
Parking
Ocean View
Balcony/Terrace
View
US $337/Night
7 Nights - US $2,356
Resort
9.6(56 Reviews)
5 Baths
21 Guests
908.47 ft²
Private Beach- Parking
- Ocean View
- Balcony/Terrace
US $154/Night
7 Nights - US $1,078
House
9.6(100 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
US $192/Night
7 Nights - US $1,344
Apartment
10.0(45 Reviews)
1 Bedroom
1 Bath
6 Guests
700 ft²
- Parking
- Kitchen
- Air Conditioner
Internet
US $328/Night
7 Nights - US $2,294
Hotel
10.0(11 Reviews)
1 Bath
779.31 ft²
- Parking
Skiing- View
- Air Conditioner
US $209/Night
7 Nights - US $1,463
House
10.0(26 Reviews)
2 Bedrooms
1 Bath
4 Guests
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $213/Night
7 Nights - US $1,490
Cabin
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $370/Night
7 Nights - US $2,590
Apartment
9.8(24 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $232/Night
7 Nights - US $1,621
Ashland Luxury Rentals
New
House
1 Bedroom
1 Bath
11 Guests
Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
US $921/Night
7 Nights - US $6,446
House
10.0(19 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $813/Night
7 Nights - US $5,694
Cabin
10.0(106 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $689/Night
7 Nights - US $4,822
House
1 Bedroom
2 Baths
5 Guests
- Hot Tub
- Air Conditioner
- Internet
Pet Friendly
US $665/Night
7 Nights - US $4,657
Cabin
10.0(109 Reviews)
4 Bedrooms
2 Baths
14 Guests
- Parking
Spa- Balcony/Terrace
- Kitchen
US $532/Night
7 Nights - US $3,722
House
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $515/Night
7 Nights - US $3,606
New
Cabin
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $431/Night
7 Nights - US $3,015
New
Cabin
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $420/Night
7 Nights - US $2,941
Ashland Pet Friendly Vacation Rentals
House
9.8(7 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $384/Night
7 Nights - US $2,689
Hotel
8.4(136 Reviews)
3 Baths
375.84 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $159/Night
7 Nights - US $1,113
Cottage
9.4(76 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $288/Night
7 Nights - US $2,014
House
9.0(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $303/Night
7 Nights - US $2,122
Hotel
7.9(180 Reviews)
20 Baths
280.4 ft²
Private Pool- Private Beach
- Oceanfront
- Hot Tub
US $119/Night
7 Nights - US $835
Apartment
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $59/Night
7 Nights - US $410
House
10.0(1 Review)
3 Bedrooms
1 Bath
5 Guests
1400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $120/Night
7 Nights - US $839
New
Cabin
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $340/Night
7 Nights - US $2,381
Ashland Large Vacation Homes
Other
9.6(5 Reviews)
6 Bedrooms
2 Baths
8 Guests
- Parking
Pool- Balcony/Terrace
- Kitchen
US $332/Night
7 Nights - US $2,323
House
9.8(27 Reviews)
4 Bedrooms
2 Baths
10 Guests
2700 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $475/Night
7 Nights - US $3,323
House
3 Bedrooms
2 Baths
10 Guests
- Air Conditioner
- Pet Friendly
Child Friendly
Laundry
US $142/Night
7 Nights - US $994
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?
Understanding the optimal time to visit can enhance your experience here, as each season in this destination offers unique opportunities to enjoy its natural beauty and local charm.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you'll enjoy longer daylight hours and vibrant outdoor activities in this region. It's an ideal time to explore scenic views and participate in seasonal events.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn brings a spectacular display of fall foliage, making it a favorite season for visitors seeking picturesque scenery and outdoor excursions in the area.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Spring (March to May)
Early spring offers a quieter experience as temperatures begin to rise, perfect for relaxing stays before the busy summer season starts.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
Winter (December to February)
The winter months attract visitors looking for peaceful escapes and wintertime beauty, with opportunities for seasonal tranquility and cozy accommodations.
Average Temperature Daytime: 20°F to 30°F - Nighttime: 0°F to 15°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.
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 outdoor grilling with a private barbecue area for memorable family dinners.
- Relax on a spacious deck or patio that offers stunning views of the surrounding natural beauty.
- Take advantage of a fire pit to gather around and share stories under the starry night sky.
- Explore nearby trails and paths perfect for hiking, biking, or nature walks right outside your door.
- Make use of a lakeside dock or access point if the property is near water, ideal for fishing or kayaking.
- Benefit from ample outdoor parking space, making your arrival and departure hassle-free.
- Depending on the property, enjoy amenities like outdoor volleyball courts or tennis areas to stay active during your stay.
Top Attractions Around Ashland
What attractions are nearby?
In this charming region, you can enjoy a variety of outdoor activities such as hiking, fishing, and exploring scenic trails just minutes from your vacation rental.
Family Activities
- Bayfield Maritime Museum: Discover local maritime history and enjoy interactive exhibits that engage children and adults alike, perfect for family outings in the region.
- Northern Great Lakes Visitor Center: Explore engaging educational displays and scenic trails that offer an enriching experience for all ages here in this beautiful part of Wisconsin.
- Castle Craig Conservation Area: Venture into nature with hikes and outdoor activities suitable for families looking to enjoy the natural beauty of the area.
- Madeline Island Ferry Ride: Take a scenic ferry trip to Madeline Island for outdoor adventures, beaches, and cultural experiences that make for a memorable family day in this area.
Adult Activities
- Exploring the Ashland Marina: You can enjoy scenic boat tours and water activities that showcase the region's stunning Lake Superior shoreline.
- Visiting the Bayfield Maritime Museum: This destination offers insights into the area's maritime history, perfect for those interested in local culture and heritage.
- Hiking along the North Country National Scenic Trail: Experience breathtaking views and diverse landscapes as you explore this popular outdoor activity here.
- Sampling local flavors at Ashland’s craft breweries: Discover artisanal brews and vibrant social scenes that highlight the area's thriving craft beverage community.
Other Places to Stay in Ashland, WI
Odanah
Moquah
Barksdale
Pilsen
Northern Great Lakes Visitor Center
Ashland Historical Museum
Maslowski Beach
White River
Chequamegon Bay Golf Course
Sanborn
Ashland Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the region's acclaimed eateries to experience authentic flavors unique to here and make your stay more memorable.
- Plan Outdoor Activities: Engage in the area's natural beauty by scheduling outdoor pursuits like hiking or boating, which showcase the best of this destination’s scenic landscape.
- Visit Nearby Attractions: Discover the local attractions and cultural sites that highlight the history and charm of the region during your visit.
- Choose the Perfect Vacation Rental: Select a well-reviewed property in the area to enjoy comfort, convenience, and easy access to all that the destination has to offer.
Transportation Options
- Ashland Transit System: This local bus service provides convenient transportation around the area, making it easy for you to explore your surroundings without hassle.
- Amtrak Stations: The nearby Amtrak station offers reliable rail travel options connecting you to major cities and further exploring this scenic region.
- Rental Cars: Numerous car rental agencies are available here, giving you the flexibility to discover the natural beauty and attractions at your own pace.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber operate in this destination, providing quick and convenient transfers from the airport or around town.
Local Customs Options
- Local Fishing Traditions: Embrace the region's strong fishing culture, where freshwater fishing is a cherished activity for both locals and visitors alike.
- Native Heritage Celebrations: Participate in events that honor the area's Native American history, highlighting long-standing customs and storytelling traditions.
- Craftsmanship and Artisanal Goods: Discover local artisans who celebrate their heritage through handcrafted goods, reflecting the region's unique cultural influences.
- Seasonal Festivals: Experience the region’s vibrant seasonal festivals that showcase community spirit and local customs throughout the year.
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:
- River Rock Cottage Is Located On The Shore Of Lake Superior On Chequamegon Bay.
- Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails.
- Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior
- North Apartment with Lake Superior Views
- A Cozy Getaway in Ashland
- Reconnect with family & friends while enjoying panoramic views of Lake Superior
- Second Wind Country Inn
- Charming 2-bedroom farmhouse in serene Ashland with AC
- Cozy Cabin Overlooking Chequamegon Bay in Ashland, Wisconsin
- The Ashland Home
2. 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:
3. How many Rentbyowner vacation rentals are available in Ashland?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 50 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.
4. What is the cancellation policy for vacation rentals in Ashland, Wisconsin?
Cancellation policies vary by property, so you should review the specific listing's terms before booking. Many listings offer flexible options, but it's best to confirm directly with the owner or through the booking platform.
5. Are there any additional fees I should be aware of when booking a vacation rental in this region?
Additional fees such as cleaning charges, service fees, or taxes are typically outlined in the listing details. It’s advisable to read the full description or contact the owner for clarity on any extra costs involved.
6. How do I confirm the availability of a vacation rental in the area?
Availability calendars are usually kept up-to-date on the listing page. For real-time confirmation, you can also reach out directly to the property owner or manager to ensure the dates you want are open.
7. What amenities can I expect from vacation rentals near this destination?
Amenities vary by property, but many offer essentials like Wi-Fi, kitchens, and outdoor spaces. To find accommodations that meet your needs, check the amenities list on each listing or contact the owner for specific questions.
8. Is it possible to modify or extend my stay once I've booked a vacation rental here?
Modifications or extensions depend on the property's policies and availability. To make changes, communicate directly with the owner or host through the booking platform to discuss possible arrangements.
Ashland Top Rated Vacation Rentals
Hotel
8.5(382 Reviews)
1 Bath
275.83 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $197/Night
7 Nights - US $1,376
US $279/Night
7 Nights - US $1,952
Hotel
7.7(310 Reviews)
1 Bath
- Private Pool
- Breakfast
- Parking
- Pool
US $179/Night
7 Nights - US $1,253
Hotel
7.3(201 Reviews)
7 Baths
269.1 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $109/Night
7 Nights - US $765
