26721+ Vacation Home Rentals in Chesapeake Bay |
  1. USA
  2. Chesapeake Bay

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

About Chesapeake Bay Vacation Rentals

Explore over 26721 vacation rentals in Chesapeake Bay 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 Bay 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 Bay. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Chesapeake Bay tailored to your preferences. On average, these rentals offer 737.66 ft² of space, and are priced at an average of US $338 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Chesapeake Bay 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 Bay

Type Count
Vacation Homes 11162
Holiday Apartments 7456
Cottages 610
B&B 426
Villas 276
Others 96
Cabin Rentals 94
Unique Vacation Rentals 50
Unique Vacation Rentals 12
Ski Chalet Rentals 3

Use these Quick Filters to Find a Vacation Rental in Chesapeake Bay

★ Pro Tip: Discover Your Ideal Vacation Rental in Chesapeake Bay 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 Bay, US

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

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chesapeake Bay, US

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


White House
Busch Gardens Williamsburg
National Mall
Virginia Beach Boardwalk
Washington Monument
National Aquarium in Baltimore
Colonial Williamsburg
Walter E. Washington Convention Center
George Washington University
Arlington National Cemetery
Smithsonian National Air and Space Museum
Naval Station Norfolk
Lincoln Memorial
Baltimore Cruise Terminal
University of Maryland-College Park
Johns Hopkins University
Capital One Arena
United States Capitol
Baltimore Convention Center
National Museum of Natural History

Other Places to Stay in Chesapeake Bay, US


Maryland 16,631 Properties
Northern Chesapeake Bay 10,011 Properties
Washington 3,543 Properties
District of Columbia 3,413 Properties
Norfolk - Virginia Beach 3,077 Properties
Northwest 2,037 Properties
Virginia Beach 2,007 Properties
Anne Arundel County 1,425 Properties
Baltimore 1,410 Properties
Northeast Virginia Beach 1,159 Properties
Alanton 1,121 Properties
Arlington 1,075 Properties

Complexes around Chesapeake Bay, US


Wyndham Patriots Lockoff Williamsburg 165 Properties
Phoenixpark Washington 22 Properties
Alexandria 47 Properties
Virginia Beach Oceanfrnt 94 Properties
Wyndham National Harbor 64 Properties
Inn 19 Properties
Ballston 41 Properties
Enjoy Beauty The Chesapeake Bay 41 Properties
Bethesda 33 Properties
Georgetown 27 Properties
Crystal City Arlington Va 6 Properties
Dupont Circle Nr U Street Metro Glen Mkt 12 Properties
Capitol Hill 14 Properties
Pentagon City 11 Properties
Prince George St Annapolis 6 Properties
See More Complexes

Frequently Asked Questions About Chesapeake Bay?

What are the top vacation rentals in Chesapeake Bay?

When organizing your trip to Chesapeake Bay, 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 Bay. Peruse our collection of highly-rated properties and secure your reservation today.

How many vacation rentals have private pools in Chesapeake Bay?

Uncover 1330 vacation rentals boasting private pools near Chesapeake Bay. Explore top-rated RBO homes offering access to a swimming pool:

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

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

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

Discover the ideal vacation rental in Chesapeake Bay with SunSki Resorts™. We provide an extensive selection of over 26721 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 Bay.

Nearby Neighborhood (16) 
Neighborhood Property Count
Northwest Vacation Rentals in Chesapeake Bay, US 2037
Northeast Virginia Beach Vacation Rentals in Chesapeake Bay, US 1159
Northeast Vacation Rentals in Chesapeake Bay, US 792
Capitol Hill Vacation Rentals in Chesapeake Bay, US 661
Downtown Washington D.C. Vacation Rentals in Chesapeake Bay, US 659
Downtown Baltimore Vacation Rentals in Chesapeake Bay, US 567
Crystal City Vacation Rentals in Chesapeake Bay, US 253
Dupont Circle Vacation Rentals in Chesapeake Bay, US 213
Rosslyn Vacation Rentals in Chesapeake Bay, US 194
Downtown Vacation Rentals in Chesapeake Bay, US 141
Old Town Alexandria Vacation Rentals in Chesapeake Bay, US 134
Fells Point Vacation Rentals in Chesapeake Bay, US 65
Georgetown Vacation Rentals in Chesapeake Bay, US 56
Foggy Bottom Vacation Rentals in Chesapeake Bay, US 49
Pentagon City Vacation Rentals in Chesapeake Bay, US 39
Chic's Beach Vacation Rentals in Chesapeake Bay, US 38

People Also Ask

There are 26721 Chesapeake Bay, US Vacation Rentals

Recently Booked Vacation Rentals in Chesapeake Bay