Best Vacation Homes in Upson
Condo
10.0(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
Oceanfront
Hot Tub
Skiing
Fireplace/Heating
US $232/Night
7 Nights - US $1,622
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
12 Guests
1625.35 ft²
Private Pool- Hot Tub
- Skiing
- Fireplace/Heating
US $438/Night
7 Nights - US $3,064
US $147/Night
7 Nights - US $1,026
House
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
988 ft²
- Skiing
- Fireplace/Heating
Balcony/Terrace
Kitchen
US $396/Night
7 Nights - US $2,774
House
10.0(1 Review)
2 Bedrooms
1 Bath
5 Guests
796.53 ft²
- Private Pool
- Hot Tub
- Skiing
- Fireplace/Heating
US $221/Night
7 Nights - US $1,547
House
9.6(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
Pool- Balcony/Terrace
Internet
US $257/Night
7 Nights - US $1,797
House
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Hot Tub
Spa- Skiing
US $281/Night
7 Nights - US $1,969
House
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Hot Tub
- Spa
- Skiing
US $281/Night
7 Nights - US $1,969
Upson Luxury Rentals
Ski Chalet
20 Bedrooms
22 Baths
42 Guests
- Fireplace/Heating
Pet Friendly
Air Conditioner- Internet
US $3,376/Night
7 Nights - US $23,632
Ski Chalet
10.0(1 Review)
10 Bedrooms
10 Baths
20 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $1,716/Night
7 Nights - US $12,015
Ski Chalet
10.0(1 Review)
9 Bedrooms
10 Baths
18 Guests
- Skiing
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,708/Night
7 Nights - US $11,953
House
10 Bedrooms
6 Baths
32 Guests
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $889/Night
7 Nights - US $6,225
House
9.8(16 Reviews)
5 Bedrooms
4 Baths
18 Guests
- Spa
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $539/Night
7 Nights - US $3,772
Ski Chalet
9.8(19 Reviews)
5 Bedrooms
4 Baths
18 Guests
- Spa
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $537/Night
7 Nights - US $3,756
House
5 Bedrooms
3 Baths
16 Guests
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $516/Night
7 Nights - US $3,614
House
5 Bedrooms
3 Baths
15 Guests
- Oceanfront
- Hot Tub
- Spa
- Skiing
US $516/Night
7 Nights - US $3,614
Upson Pet Friendly Vacation Rentals
Cabin
9.6(10 Reviews)
4 Bedrooms
3 Baths
12 Guests
1700 ft²
- Oceanfront
- Hot Tub
- Spa
- Skiing
US $325/Night
7 Nights - US $2,275
US $133/Night
7 Nights - US $930
US $156/Night
7 Nights - US $1,091
Cabin
9.4(12 Reviews)
4 Bedrooms
3 Baths
12 Guests
1622 ft²
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $369/Night
7 Nights - US $2,581
Ski Chalet
9.4(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $469/Night
7 Nights - US $3,286
New
Apartment
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $321/Night
7 Nights - US $2,247
Upson Large Vacation Homes
House
10.0(19 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Skiing
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $514/Night
7 Nights - US $3,600
Ski Chalet
10.0(1 Review)
6 Bedrooms
2 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Parking
US $371/Night
7 Nights - US $2,599
House
9.6(27 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Skiing
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $475/Night
7 Nights - US $3,326
Cabin
9.6(5 Reviews)
3 Bedrooms
2 Baths
10 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $340/Night
7 Nights - US $2,378
House
9.4(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $387/Night
7 Nights - US $2,708
Ski Chalet
10.0(1 Review)
6 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $673/Night
7 Nights - US $4,708
Condo
9.4(27 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $451/Night
7 Nights - US $3,155
Why Choose Rent By Owner for your Upson 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 Upson
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can greatly enhance your experience, so consider planning your trip during the seasons when this destination offers optimal weather and activities in the region.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you'll enjoy extended daylight and pleasant weather, ideal for outdoor activities and exploring the natural beauty of this area.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
In early fall, the region is vibrant with colorful foliage, making it a perfect time to experience the scenic views and outdoor adventures.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
The winter season offers a peaceful escape with snowy landscapes and fewer visitors, providing a serene atmosphere for quiet getaways.
Average Temperature Daytime: 20°F to 30°F - Nighttime: 0°F to 15°F
Spring (March to May)
Early spring brings a gradual thaw and blooming scenery, making it a less crowded yet charming time to visit and enjoy the area's natural renewal.
Average Temperature Daytime: 40°F to 55°F - Nighttime: 25°F to 35°F
Weekly Weather Forecast for Upson
How to Book Your Upson 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 Upson
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 seating area where you can relax and take in the scenic views of the surrounding region.
- Take advantage of a spacious deck or patio perfect for outdoor dining and entertaining during your stay.
- Explore well-maintained walking trails directly from your property, ideal for nature walks and outdoor adventures.
- Benefit from access to a fire pit for cozy evenings under the stars after a day of exploring the area.
- Make use of outdoor recreational equipment such as kayaks, paddleboards, or bikes often available at the property.
- Relax by a private outdoor pool or hot tub, providing a luxurious way to unwind during warmer months or cooler seasons.
- Appreciate beautifully landscaped gardens or yard space that invite outdoor activities and family fun.
Top Attractions Around Upson
What attractions are nearby?
Enhance your stay by exploring nearby outdoor activities and local attractions that showcase the natural beauty and charm of this region, making your visit to Upson a memorable adventure.
Family Activities
- Upson Lake Recreation Area: Enjoy a family day by the water with swimming, fishing, and picnicking in this scenic spot nearby your vacation rentals.
- Public Forest Trails: Explore the region’s lush landscapes on hiking or biking trails suitable for all ages, offering outdoor adventures just outside your accommodation.
- Local Wildlife Viewing: Discover the region’s diverse fauna through guided tours or leisurely observation around natural habitats close to where you stay.
- Family-Friendly Camping Sites: Spend memorable nights under the stars at designated campgrounds that provide easy access to nature and outdoor activities here.
Adult Activities
- Hiking and Nature Walks: Explore scenic trails that wind through the pristine wilderness, offering an immersive experience in the region's natural beauty.
- Fishing and Boating: Spend your days enjoying tranquil fishing spots and boating opportunities on nearby lakes, perfect for relaxing as an adult visitor.
- Wildlife Observation: Discover diverse wildlife by visiting local conservation areas, ideal for those interested in birdwatching and nature photography.
- Local Dining Experiences: Savor regional cuisine at charming restaurants and eateries that highlight the area’s culinary flavors, enriching your visit here.
Other Places to Stay in Upson, WI
Whitecap Mountains
Upson Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Outdoor Activities: Make the most of your stay by engaging in hiking, fishing, or boating opportunities that highlight the natural beauty of this region.
- Visit Nearby Natural Attractions: Take time to discover scenic spots and tranquil areas close to your rental, enhancing your experience of the area's pristine environment.
- Plan Your Trip During Off-Peak Seasons: Visiting during less busy times can offer a more relaxed atmosphere and better availability for your preferred vacation rentals.
- Utilize Trusted Booking Platforms: Book through reputable vacation rentals to ensure a seamless and dependable stay in the area’s accommodation options.
Transportation Options
- Upson County Airport: You can access the region conveniently through this small local airport, ideal for quick arrivals and departures.
- Regional Bus Services: Public bus transportation connects travelers to nearby towns and cities, making it a practical option for exploring the area without a car.
- Rental Car Services: Several rental agencies operate in the region, allowing you flexibility to explore Upson and its surroundings at your own pace.
- Taxi and Rideshare Options: Taxis and rideshare services are available here, providing a reliable way to get around when you prefer not to drive yourself.
Local Customs Options
- Local Craftsmanship: You’ll notice that the region values handmade goods, reflecting a deep-rooted appreciation for artisanal skills during your stay.
- Traditional Festivals: Participating in local festivals offers you a glimpse into the area's customs and community spirit throughout the year.
- Respect for Nature: The community places a strong emphasis on environmental preservation, which is evident in outdoor etiquette and conservation efforts here.
- Community Gatherings: Regular social events foster a welcoming atmosphere where visitors like you can experience genuine local hospitality.
Upson Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Upson?
There are a lot of options in Upson. If you plan on staying in the Upson area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Upson:
- Ski-in ski-out 3 Bdrm Chalet w sauna on slopes & lake - Sleeps 8
- Twin Peaks - House 2
- Family friendly ski-in/ski out Chalet Whitecap Mountain with high end boot dryer
- Upson Ski-In/Ski-Out, End-Unit Cabin w/Fireplace!
- Ski-In/Ski-Out Condo in Upson - Walk to Lake
- Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2
- Charming, ski-in, ski-out, lake-view chalet w/10 bedrooms, kitchen and AC.
- Million Dollar View! Whitecap Mtns Ski Resort Home
- Alpenhaus Upper ~ Whitecap Ski Village!
- Stunning 3 bed/2bath Cottage with lake frontage. Winter ski in/out Whitecap Mtn
2. Which vacation homes in Upson are best for families?
If you are looking for a family-friendly vacation home in Upson, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Upson:
3. How many Rentbyowner vacation rentals are available in Upson?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 38 in the Upson 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 Upson.
4. What is the cancellation policy for vacation rentals in this area?
The cancellation policy varies depending on the listing owner. You should review the specific property’s policy on the listing page or contact the host directly for detailed information.
5. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or taxes are often outlined on the listing page. It’s best to read the details carefully or reach out to the host for clarification before confirming your reservation.
6. How can I ensure that my booking within this destination is secure?
All bookings are processed through a trusted platform that provides secure payment options. Confirm the listing’s reviews and host credentials to ensure a reliable stay.
7. What amenities are typically included with vacation rentals in this region?
Most listings in this destination offer essential amenities like Wi-Fi, kitchen facilities, and linens. To confirm the specific amenities available, check the property description or contact the host directly.
8. How do I find the most suitable vacation rental in this area for my needs?
Use the search filters on the booking site to narrow down options based on your preferences such as size, amenities, and price range. Reading reviews and contacting hosts can also help you select the perfect place for your stay.
Upson Top Rated Vacation Rentals
Ski Chalet
10.0(20 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Skiing
- Fireplace/Heating
- Pool
US $355/Night
7 Nights - US $2,485
House
10.0(14 Reviews)
3 Bedrooms
3 Baths
9 Guests
1600 ft²
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $278/Night
7 Nights - US $1,944
House
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
- Hot Tub
- Fireplace/Heating
- Pool
Ocean View
US $297/Night
7 Nights - US $2,078
House
3 Bedrooms
2 Baths
9 Guests
- Oceanfront
- Hot Tub
- Spa
- Skiing
US $384/Night
7 Nights - US $2,690
