Chesapeake Ski Chalets

Why Choose Rent By Owner for your Chesapeake Ski Chalets?

What makes our Ski Chalets special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Chesapeake

When should you plan your Ski Chalets stay?

Timing your visit to Chesapeake, Virginia, ensures you can enjoy the area’s serene winter atmosphere and optimal conditions for your ski chalet getaway, making it the perfect choice for travelers seeking a tailored vacation experience in this inviting destination.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, you can experience the peak engagement for outdoor activities in the area, making it an ideal time for booking cozy ski chalets that provide warmth after a day on the slopes.

Average Temperature Daytime: around 40°F (4°C) - Nighttime: near 25°F (-4°C)
spring
Early Spring (March to April)

As the region transitions into spring, this period still offers excellent winter sports conditions, drawing visitors seeking the last of the snow and a vibrant atmosphere for their getaway.

Average Temperature Daytime: approximately 50°F (10°C) - Nighttime: about 30°F (-1°C)

Off-Season Highlights

image
Late Spring (May to June)

In late spring, the area sees fewer tourists, providing a quieter setting for those wanting to enjoy a peaceful retreat in their chosen ski chalet.

Average Temperature Daytime: around 70°F (21°C) - Nighttime: roughly 50°F (10°C)
image
Fall (September to November)

During fall, the region's natural beauty shines with colorful foliage, creating a scenic backdrop for your stay while avoiding the busy winter season rush.

Average Temperature Daytime: approximately 65°F (18°C) - Nighttime: about 45°F (7°C)

Weekly Weather Forecast for Chesapeake

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.

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 or patio to relax and take in the scenic views of Chesapeake's surroundings.
  • Make the most of your stay with access to well-maintained walking trails or nature paths nearby.
  • Benefit from a spacious backyard or garden space perfect for outdoor activities or family gatherings.
  • Take advantage of outdoor grilling facilities to prepare delicious meals amidst the fresh air.
  • Relax by a cozy outdoor fire pit, ideal for evening conversations under the stars.
  • Access to a swimming pool or hot tub may be available for ultimate relaxation after a day exploring the region.
  • Utilize convenient parking areas designed to accommodate your vehicle securely during your stay.
image
image

Family Activities

  • Virginia Aquarium & Marine Science Center Engage your family with interactive exhibits and marine life displays at this acclaimed aquarium, providing an educational experience right in this destination.
  • Oak Grove Lake Park Enjoy outdoor fun by exploring walking trails, picnicking areas, and the scenic lake perfect for family outings in the area.
  • Chesapeake Planetarium Introduce your children to the wonders of astronomy through engaging shows and immersive presentations at this local planetarium.
  • Great Dismal Swamp National Wildlife Refuge Experience nature firsthand on guided tours and nature walks through one of the region’s most remarkable wildlife habitats, ideal for family adventures.
image

Adult Activities

  • Chesapeake City Park Enjoy a relaxing day at the park, with opportunities for outdoor picnics, walking trails, and engaging events that showcase the local community.
  • The Great Dismal Swamp National Wildlife Refuge Explore this vast wildlife refuge ideal for nature walks, bird watching, and immersing yourself in the region’s diverse ecosystem.
  • Oak Grove Lake Park Experience serene lakeside views perfect for fishing, kayaking, or simply unwinding amidst scenic surroundings near here.
  • Deep Creek Lock Park Discover historical lock systems and enjoy picturesque views along the canal, making it a great spot for leisurely strolls and photography.

Other Places to Stay in Chesapeake, VA

Deep Creek South
Cahoon Plantation Golf Course
Chesapeake City County
Adventure Kayak Tours Day Tours
Portlock Galleries at SoNo
Chesapeake Veterans' Memorial
Chesapeake City Hall
Western Branch North
Greenbrier West
Greenbrier East

Chesapeake Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining experiences: Take advantage of the area's array of restaurants to enjoy authentic regional cuisine and make your stay more memorable.
  • Plan outdoor activities: Utilize the region’s parks and scenic spots to engage in activities like hiking or picnicking, enhancing your overall visit.
  • Visit nearby cultural sites: Discover the rich history and culture around the area by exploring museums or historic landmarks to deepen your connection to this destination.
  • Book accommodations early: Secure your preferred ski chalets well in advance to ensure a seamless and stress-free stay during peak seasons or popular travel periods.

Transportation Options

  • Chesapeake Regional Airport This regional airport offers convenient domestic flights, making it easy for you to access the area when planning your stay in a cozy ski chalet.
  • Amtrak Passenger Service Providing rail options, Amtrak connects here to major cities, offering a scenic and relaxing transportation alternative for traveling within the region.
  • Local Bus Services The area's public bus system provides affordable and accessible transportation around Chesapeake, ideal for exploring local amenities near your accommodation.
  • Taxi and Rideshare Services Reliable taxi companies and rideshare options like Uber and Lyft are readily available, ensuring seamless travel throughout the destination during your vacation.

Local Customs Options

  • Southern Hospitality: You’ll notice a warm and welcoming attitude from locals, reflecting the region's tradition of friendliness and community spirit.
  • The area embraces its maritime roots with customs such as seafood festivals and boat parades that highlight its connection to water activities.
  • Historical Celebrations: Visitors often experience local events that honor Chesapeake’s rich history, including reenactments and heritage festivals throughout the year.
  • Gullah Cultural Influence: You may encounter unique cultural expressions rooted in Gullah traditions, showcasing the area's diverse heritage and customs.

Frequently Asked Questions About Chesapeake Rental Ski Chalets

2. How many Ski Chalets are available in Chesapeake?

Currently, the total number of properties listed by RBO in 2026 is over 179 in the Chesapeake area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Chesapeake. 

3. What is the cancellation policy for booking a ski chalet in Chesapeake, Virginia?

Cancellation policies vary by property; please review the specific listing details or contact the owner directly to understand the terms and any applicable fees for cancellations.

4. Are there any additional fees or deposits required when booking a ski chalet in this area?

Additional fees such as cleaning fees, security deposits, or service charges may apply. Details are provided on each listing, and you should confirm these before completing your reservation.

5. How do I ensure the ski chalet I choose is suitable for my group size and needs?

Each listing includes detailed information about capacity, amenities, and layout. Review the property description thoroughly and reach out to the host if you have specific requirements.

6. What amenities are typically available in ski chalets near Chesapeake, Virginia?

Most properties offer essential amenities like Wi-Fi, heating, kitchen facilities, and parking, with some providing additional features such as fireplaces or outdoor spaces. Check individual listings for precise details.

7. How can I contact the property owner if I have questions before booking a ski chalet?

You can use the messaging feature on the booking platform to communicate directly with the property owner or manager for any inquiries regarding the stay or specific accommodations.

More Rentals You May Like Near Chesapeake