Bespoke Usa Travel - Vacation Rentals in Chesapeake City

Inn At The Canal Bed & Breakfast From US $231
         

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8.6 (504 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal From US $354
         

Chesapeake Bay House with Dock & Private Beach From US $483
         

10.0 (178 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Chesapeake City Quiet Overlook From US $523
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Waterfront Lodge packed with Amenities From US $886
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Chesapeake City

Over 64+ Luxury Places to Stay in or Near Chesapeake City
Chesapeake Point | Waterfront w/HOT TUB + Beach! From US $1,348
         

9.8 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Chesapeake City

Over 9+ Top-Rated Vacation Rentals with a Pool in or Near Chesapeake City
Veazey Cove | 8,000 sq ft Waterfront Home w/Pool + Hot Tub! From US $849
         

9.6 (35 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Stunning waterfront villa, indoor pool, kids swingset From US $1,295
         

5.0 (1 Review)
Villa
  • Air Conditioner
  • Pet Friendly
  • Pool

Pet-Friendly Vacation Rentals in Chesapeake City

Over 10+ Pet-Friendly Vacation Rentals in or Near Chesapeake City
Charming 2-bedroom cabin close to Fair Hill on horse farm From US $369
         

9.6 (14 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Oasis Waterfront Retreat on the Chesapeake's Elk River. From US $243
         

10.0 (84 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
The Cove On The Waterfront From US $238
         

10.0 (75 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
-Sunset River Shack-Amazing water views of the upper Chesapeake bay From US $295
         

9.8 (16 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunset River Shack -amazing waterfront view From US $308
         

9.4 (3 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunset River Cottage -The perfect waterfront getaway! From US $298
         

9.0 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Chesapeake City

Over 4+ Large Vacation Homes & Villas in or Near Chesapeake City
New! Chesapeake Bay house with amazing views From US $575
         

4.8 (30 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

Chesapeake City Varoom and Airbnb Places to Stay Under $200

Over 11+ Chesapeake City Varoom and Airbnb Places to Stay Under $200
Country Get Away 1 Bedroom Apartment From US $82
         

9.8 (40 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Historic Chesapeake City Stay From US $154
         

9.0 (19 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Adventure Mobile From US $163
         

New
House
  • Air Conditioner
  • Security/Safety
  • Child Friendly
Short Term Water Oriented Furnished Apartment From US $159
         

10.0 (31 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Bonfire by the Creek From US $186
         

9.8 (87 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Rustic 1 room Cabin
New
From US $90
         

New
Cabin
  • Security/Safety
  • Bedding/Linens
  • Child Friendly
Quiet & Private with Fire Pit Out Back! From US $186
         

9.8 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Comfy, Cozy & Perfect! From US $186
         

9.8 (38 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Chesapeake City

Over 14+ Instantly Bookable Vacation Homes in or Near Chesapeake City
Patio & Water Views: Serene Bohemia River Escape! From US $387
         

Chesapeake City Charm at the Boho House! From US $555
         

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC From US $201
         

Waterfront House on the Upper Chesapeake Bay From US $209
         

9.6 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Waterfront Cottage on the C&D Canal! From US $562
         

8.0 (5 Reviews)
Cottage
  • Air Conditioner
  • TV
  • Balcony/Terrace

About Chesapeake City Vacation Rentals

With more than 73 Chesapeake City vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bespokeusatravel 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 City.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bespokeusatravel Chesapeake City, 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 City. Places to stay near Chesapeake City are 1561.7 ft² on average, with prices averaging $617 a night.

Bespokeusatravel makes it easy and safe to find and compare vacation rentals in Chesapeake City 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 City

Type Count
Vacation Homes 50
Cottages 9
Holiday Apartments 5
Cabin Rentals 4
Villas 3
B&B 1
Others 1

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

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

Weather in Chesapeake City

View the weather forecast for Chesapeake City before booking your Chesapeake City 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