Winters Vacations Rentals - Vacation Rentals in Northern Chesapeake Bay

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

10.0 (3 Reviews)
Villa
  • 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
PERFECT LOCATION in the heart of history From US $447
         

10.0 (213 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Eastern Shore beach cottage get-away From US $312
         

10.0 (138 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Northern Chesapeake Bay

Over 10000+ Luxury Places to Stay in or Near Northern 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 Northern Chesapeake Bay

Over 3035+ Top-Rated Vacation Rentals with a Pool in or Near Northern 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
Heart of the City - HalfBlock to METRO - Columbia Heights. From US $70
         

10.0 (162 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
St. Michael's Premier In-Town Rental with heated pool. From US $765
         

10.0 (147 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Northern Chesapeake Bay

Over 5286+ Pet-Friendly Vacation Rentals in or Near Northern Chesapeake Bay
Bluebird Suites DC Financial District From US $161
         

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

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10.0 (86 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Colorful Suite in CapitolHill+ Free Parking From US $130
         

9.4 (74 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Del Ray Designer Home walk to Shops, Cafes, Fun From US $414
         

9.6 (62 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV

Large Vacation Homes & Villas in Northern Chesapeake Bay

Over 2069+ Large Vacation Homes & Villas in or Near Northern Chesapeake Bay
Multi-Generational Waterfront Retreat with Pool! From US $833
         

10.0 (70 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
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
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock From US $874
         

9.8 (75 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious, Relaxing, 4 Bd 3.5 Ba Home In Petworth! From US $352
         

8.0 (87 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Northern Chesapeake Bay

Over 4534+ Wheelchair Accessible Vacation Homes in or Near Northern Chesapeake Bay
Churchill Living City Center From US $285
         

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New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
2BR Urban Retreat | Gym, Prkng & Scenic Rooftop From US $295
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Downtown 2BR in Woodmont Triangle | Steps to Metro From US $253
         

6.8 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Woodmont Triangle| Pet-friendly 1BR | nr Glen Echo Park From US $156
         

9.4 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Stay in the landmark Lighthouse! From US $354
         

10.0 (107 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
New Downtown Annapolis Condo With Free Parking From US $290
         

10.0 (34 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Northern Chesapeake Bay Varoom and Airbnb Places to Stay Under $200

Over 6146+ Northern Chesapeake Bay Varoom and Airbnb Places to Stay Under $200
Newly renovated Gem of a Georgetown Home From US $170
         

9.6 (51 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Designer Fashion Loft 1 Bedroom Apartment -Royalty Homes From US $137
         

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

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10.0 (56 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Brand new and modern apartment on Red Line! From US $150
         

10.0 (59 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Northern Chesapeake Bay

Over 9133+ Instantly Bookable Vacation Homes in or Near Northern Chesapeake Bay
Posh 2BR Retreat | Gym, Prkng & Scenic Rooftop From US $286
         

New
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Rare find! Chic cottage, salt water heated pool May 15-Oct15. From US $871
         

About Northern Chesapeake Bay Vacation Rentals

With more than 15651 Northern Chesapeake Bay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Wintersvacationsrentals 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 Northern Chesapeake Bay.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Wintersvacationsrentals Northern 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 Northern Chesapeake Bay. Places to stay near Northern Chesapeake Bay are 764.69 ft² on average, with prices averaging $350 a night.

Wintersvacationsrentals makes it easy and safe to find and compare vacation rentals in Northern 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 Northern Chesapeake Bay

Type Count
Vacation Homes 6484
Holiday Apartments 5312
Hotels with Suites 2215
B&B 343
Cottages 219
Resorts 142
Villas 77
Others 50
Cabin Rentals 42
Hostels 16
Ski Chalet Rentals 3

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

Pro Tip: Wintersvacationsrentals makes it easy to compare the best listings on Wintersvacationsrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Wintersvacationsrentals 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 Northern Chesapeake Bay.

Weather in Northern Chesapeake Bay

View the weather forecast for Northern Chesapeake Bay before booking your Northern 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