Beach Haven Vacation Rentals - Vacation Rentals in Chesapeake Bay

Great Location with 2 King beds 2 queen beds From US $225
         

10.0 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Breathtaking Waterfront Estate From US $887
         

10.0 (71 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Blake House Historic Estate with Private Inn From US $938
         

10.0 (21 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
BRAND NEW immaculate villa From US $657
         

10.0 (10 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Chesapeake Bay

Over 10000+ Luxury Places to Stay in or Near Chesapeake Bay
Sailor's Sunrise Cottage - Chesapeake Bay From US $10,616
         

9.4 (54 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming Oasis near Metro: Arcade, Coffee, Parks From US $10,606
         

9.4 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Chesapeake Bay

Over 6663+ Top-Rated Vacation Rentals with a Pool in or Near Chesapeake Bay
Family and Pet-Friendly, Waterfront with Pier From US $275
         

10.0 (265 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Stunning Waterfront Cottage with Breathtaking Views! From US $449
         

10.0 (220 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Peaceful Cambridge Home on Jenkins Creek From US $371
         

10.0 (213 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Chesapeake Bay

Over 8474+ Pet-Friendly Vacation Rentals in or Near Chesapeake Bay
Cottage on a Private Island in the York River From US $215
         

10.0 (359 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Bluebird Suites DC Financial District From US $161
         

|
8.9 (44 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Hummingbird Inn From US $331
         

|
10.0 (86 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Eastern Shore beach cottage get-away From US $312
         

10.0 (138 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Kingsbay Mansion Bayhouse From US $799
         

10.0 (39 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Chesapeake Bay

Over 3759+ Large Vacation Homes & Villas in or Near Chesapeake Bay
Pentagon City Luxury Apartment From US $126
         

5.8 (17 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
USNA Luxury Home, parking, pet friendly From US $910
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Baydream Believer From US $1,003
         

10.0 (87 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Multi-Generational Waterfront Retreat with Pool! From US $833
         

10.0 (70 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Chesapeake Bay

Over 6458+ Wheelchair Accessible Vacation Homes in or Near Chesapeake Bay
Churchill Living City Center From US $285
         

|
New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern 2BR Oasis with Scenic Rooftop & Gym From US $301
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Chesapeake Bay Varoom and Airbnb Places to Stay Under $200

Over 10500+ Chesapeake Bay Varoom and Airbnb Places to Stay Under $200
Designer Fashion Loft 1 Bedroom Apartment -Royalty Homes From US $137
         

|
5.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Internet
Inn at Huntingfield Creek From US $160
         

|
10.0 (56 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Newly renovated Gem of a Georgetown Home From US $170
         

9.6 (51 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Brand new and modern apartment on Red Line! From US $150
         

10.0 (59 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Colorful Suite in CapitolHill+ Free Parking From US $130
         

9.4 (74 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Chesapeake Bay

Over 15038+ Instantly Bookable Vacation Homes in or Near Chesapeake Bay
2BR Urban Retreat | Gym, Prkng & Scenic Rooftop From US $295
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
PERFECT LOCATION in the heart of history From US $447
         

10.0 (213 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
SANDY HILL SUNSETS From US $248
         

10.0 (74 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
All the comforts of home! From US $251
         

10.0 (72 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Chesapeake Bay Vacation Rentals

With more than 296 Chesapeake Bay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Beachhavenvacationrentals and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chesapeake Bay.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Beachhavenvacationrentals Chesapeake Bay, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chesapeake Bay. Places to stay near Chesapeake Bay are 1339.17 ft² on average, with prices averaging $421 a night.

Beachhavenvacationrentals makes it easy and safe to find and compare vacation rentals in Chesapeake Bay with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Chesapeake Bay

Type Count
Villas 263
Holiday Apartments 18
Vacation Homes 13
B&B 1
Resorts 1

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

Pro Tip: Beachhavenvacationrentals makes it easy to compare the best listings on Beachhavenvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Beachhavenvacationrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chesapeake Bay.

Weather in Chesapeake Bay

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