168+ Vacation Home Rentals in Chesapeake |
  1. USA
  2. Virginia
  3. Norfolk - Virginia Beach
  4. Chesapeake

Chesapeake Vacation Rentals & Ski-in/Ski-out Homes

About Chesapeake Vacation Rentals

Explore over 168 vacation rentals in Chesapeake with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Chesapeake for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Chesapeake. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Chesapeake tailored to your preferences. On average, these rentals offer 448.85 ft² of space, and are priced at an average of US $190 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Chesapeake at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

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Top Types of Ski Accommodations in Chesapeake

Type Count
Vacation Homes 59
Holiday Apartments 20
Cottages 2
Others 1
Unique Vacation Rentals 1

Use these Quick Filters to Find a Vacation Rental in Chesapeake

★ Pro Tip: Discover Your Ideal Vacation Rental in Chesapeake with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.

Weather in Chesapeake, VA

View the weather forecast for Chesapeake before booking your Chesapeake Vacation Rentals to confirm your best time to go.

December - February
High 62°F       Low 35°F
March - May
High 76°F       Low 41°F
June - August
High 90°F       Low 69°F
September - November
High 80°F       Low 44°F

Top Attractions Around Chesapeake, VA

Sunski offers a large selection of top attractions around Chesapeake . Research things to do on your vacation before you visit Chesapeake.


Greenbrier Mall
Chesapeake Square Mall
Great Dismal Swamp National Wildlife Refuge
Chesapeake Conference Center
Chesapeake Veterans' Memorial
Chesapeake City Park
Chesapeake City Hall
Chesapeake Arboretum
Chesapeake Golf Club
Chesapeake Central Library
Jillian's Billiards
Portlock Galleries at SoNo
Oak Grove Lake Park
Float First
Cahoon Plantation Golf Course
Adventure Kayak Tours Day Tours
Lake Drummond
Chesapeake Regional Medical Center
Virginia Beach Boardwalk
Naval Station Norfolk

Other Places to Stay in Chesapeake, VA


Great Bridge East 535 Properties
Cahoon Plantation Golf Course 170 Properties
Chesapeake City County 166 Properties
Deep Creek South 165 Properties
Portlock Galleries at SoNo 154 Properties
Chesapeake Veterans' Memorial 154 Properties
Great Bridge 137 Properties
Greenbrier West 82 Properties
South Norfolk 79 Properties
Jolliff 45 Properties
Greenbrier East 38 Properties
Western Branch North 29 Properties

Complexes around Chesapeake, VA


Inn 3 Properties
Breakfast The Virginia Beach Business District 3 Properties
Stay America Suites Chesapeake Crossways Blvd 3 Properties
Comfort Norfolk 2 Properties
Econo Lodge Chesapeake Route 2 Properties
Breakfast Business Travelers 1 Properties
Rental 1 Properties

Frequently Asked Questions About Chesapeake?

What are the top vacation rentals in Chesapeake?

When organizing your trip to Chesapeake, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Chesapeake. Peruse our collection of highly-rated properties and secure your reservation today.

How many vacation rentals have private pools in Chesapeake?

Uncover 6 vacation rentals boasting private pools near Chesapeake. Explore top-rated RBO homes offering access to a swimming pool:

Which vacation homes or resorts in Chesapeake are best for families?

Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Chesapeake. Enjoy great views, locations and save money with SunSki Resorts.™

How many SunSkiResorts vacation rentals or resorts are available in Chesapeake?

Discover the ideal vacation rental in Chesapeake with SunSki Resorts™. We provide an extensive selection of over 168 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Chesapeake.

Nearby Neighborhood (7) 
Neighborhood Property Count
Greenbrier East Vacation Rentals in Chesapeake, Virginia 38
Western Branch North Vacation Rentals in Chesapeake, Virginia 29
Greenbrier West Vacation Rentals in Chesapeake, Virginia 82
Great Bridge Vacation Rentals in Chesapeake, Virginia 137
Deep Creek South Vacation Rentals in Chesapeake, Virginia 165
Churchland Vacation Rentals in Chesapeake, Virginia 73
Great Bridge East Vacation Rentals in Chesapeake, Virginia 535

People Also Ask

There are 168 Chesapeake, VA Vacation Rentals

Recently Booked Vacation Rentals in Chesapeake