Best Vacation Homes in Calvert County
3000 ft²
10 Guests
1 Bedroom
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
AU $1,139/Night
For 7 Nights AU $7,972
1302.43 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- View
AU $405/Night
For 7 Nights AU $2,834
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $972/Night
For 7 Nights AU $6,807
5 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Air Conditioner
- Internet
AU $662/Night
For 7 Nights AU $4,634
2400.35 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $690/Night
For 7 Nights AU $4,828
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
AU $547/Night
For 7 Nights AU $3,827
16 Guests
5 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Child Friendly
AU $512/Night
For 7 Nights AU $3,584
7 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
AU $240/Night
For 7 Nights AU $1,684
Calvert County Luxury Rentals
12 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
AU $2,482/Night
For 7 Nights AU $17,375
3003.13 ft²
10 Guests
1 Bedroom
4 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
AU $1,701/Night
For 7 Nights AU $11,908
4004.17 ft²
14 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $1,598/Night
For 7 Nights AU $11,184
4000 ft²
14 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
AU $1,514/Night
For 7 Nights AU $10,600
13 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $1,359/Night
For 7 Nights AU $9,514
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Pet Friendly
AU $1,322/Night
For 7 Nights AU $9,256
2868 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
AU $1,264/Night
For 7 Nights AU $8,851
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
AU $1,157/Night
For 7 Nights AU $8,098
Calvert County Pet Friendly Vacation Rentals
1300 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cabin
- Fireplace/Heating
- Pool
- Ocean View
AU $487/Night
For 7 Nights AU $3,407
16501.07 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Beach
- Oceanfront
- Fireplace/Heating
AU $759/Night
For 7 Nights AU $5,310
1600 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $592/Night
For 7 Nights AU $4,144
1302.43 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Spa
- Fireplace/Heating
- View
AU $772/Night
For 7 Nights AU $5,405
800 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $327/Night
For 7 Nights AU $2,293
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
AU $796/Night
For 7 Nights AU $5,568
300 ft²
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Cottage
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
AU $562/Night
For 7 Nights AU $3,932
6 Guests
2 Bedrooms
1 Bathroom
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
AU $392/Night
For 7 Nights AU $2,745
Calvert County Large Vacation Homes
2194 ft²
10 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $442/Night
For 7 Nights AU $3,091
1603.82 ft²
11 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- Balcony/Terrace
- View
- Parking
AU $311/Night
For 7 Nights AU $2,174
10 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $465/Night
For 7 Nights AU $3,255
2002.09 ft²
11 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Pool
- Pet Friendly
- Parking
AU $688/Night
For 7 Nights AU $4,818
5000 ft²
12 Guests
4 Bedrooms
5 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
AU $975/Night
For 7 Nights AU $6,826
10 Guests
4 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Child Friendly
AU $824/Night
For 7 Nights AU $5,772
1740 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $696/Night
For 7 Nights AU $4,869
11 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $482/Night
For 7 Nights AU $3,372
Why Choose Rent By Owner for your Calvert County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Calvert County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as the area offers unique attractions and scenic beauty that vary throughout the seasons, making it ideal to plan your vacation when the weather and local events align with your preferences.
Peak Season Highlights
Late Spring to Early Summer (May - June)
This period offers warm weather ideal for exploring the area's scenic landscapes and outdoor activities, making it a popular time for visitors seeking vibrant local events.
Average Temperature Daytime: 75°F - Nighttime: 60°F
Early Fall (September - October)
During these months, the region experiences mild temperatures and beautiful fall foliage, perfect for enjoying outdoor adventures and serene coastal views.
Average Temperature Daytime: 70°F - Nighttime: 55°F
Off-Season Highlights
Winter (December - February)
The quiet winter months bring cooler temperatures and fewer crowds, offering a peaceful retreat for those looking to escape the busier seasons here.
Average Temperature Daytime: 45°F - Nighttime: 30°F
Late Fall to Early Winter (November - December)
As the area transitions into winter, you can enjoy fewer tourists and more affordable rental options while experiencing the calm of the off-peak season.
Average Temperature Daytime: 50°F - Nighttime: 40°F
Weekly Weather Forecast for Calvert County
How to Book Your Calvert County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Calvert County
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor seating areas such as patios or decks to relax and unwind amidst scenic views.
- Take advantage of private or shared grilling stations to prepare delicious meals outdoors.
- Make the most of spacious yards or gardens perfect for leisurely walks or outdoor activities.
- Look for properties with access to nearby water features, including docks or waterfront areas, ideal for boat outings or fishing.
- Utilize outdoor fire pits for cozy evenings under the stars with family and friends.
- Find accommodations with swimming pools or hot tubs to add a touch of luxury to your stay here.
- Explore properties featuring outdoor recreational equipment, such as kayaks or paddleboards, for enhanced adventure in the region’s waterways.
Top Attractions Around Calvert County
What attractions are nearby?
While staying here, you can enjoy a variety of outdoor activities and scenic explorations just moments from your vacation rental in Calvert County, Maryland, offering you the perfect opportunity to experience the natural beauty and tranquil atmosphere that make this destination so special.
Family Activities
- Calvert County Marine Museum: Explore this family-friendly museum where you can learn about local maritime history and enjoy hands-on exhibits that captivate children and adults alike.
- Flag Ponds Nature Park: Spend a day at this scenic park, perfect for beachcombing, picnicking, and discovering the region’s natural beauty along Maryland’s shores with your loved ones.
- Calvert Cliffs State Park: Embark on an outdoor adventure by exploring the hiking trails and hunting for fossils along the picturesque cliffs overlooking the Chesapeake Bay.
- Bayside History Museum: Discover the region's rich history through engaging exhibits designed to educate and entertain young explorers and their families visiting here.
Adult Activities
- Boating and Sailing on the Patuxent River: You can enjoy exploring the scenic waterways with boat rentals or sailing excursions, offering a peaceful way to experience the region's natural beauty.
- Visiting Calvert Marine Museum: This museum provides insights into maritime history, featuring exhibits that showcase the area's rich nautical heritage, perfect for a leisurely day of learning.
- Wine Tasting at Local Vineyards: Discover the flavors of the region by visiting nearby vineyards, where you can indulge in tastings amid picturesque vineyard landscapes.
- Relaxing at Calvert Cliffs State Park: Spend your time hiking along trails that lead to stunning cliffs and discovering unique geological formations, all while enjoying the tranquility of the coastal environment.
Other Places to Stay in Calvert County, MD
Dunkirk
Fridays Creek Winery
Calvert Cliffs State Park
Chesapeake Beach
Dowell
Port Republic
Prince Frederick
Calvert Beach-Long Beach
North Beach
Chesapeake Ranch Estates-Drum Point
St. Leonard
Calvert County Travel Tips
How Can You Make the Most of Your Stay?
- Explore the Local Waterfronts: Take advantage of the area's scenic waterways by engaging in activities like kayaking or fishing, which showcase the natural beauty of your vacation rental’s proximity to the water.
- Visit Nature and Wildlife Areas: Discover the region's parks and wildlife refuges to enjoy serene outdoor experiences and observe local flora and fauna during your stay.
- Sample Regional Cuisine: Indulge in the area's fresh seafood and locally-inspired dishes at nearby eateries or markets, enriching your visit with authentic flavors.
- Plan Off-the-Beaten-Path Excursions: Venture beyond typical tourist spots to uncover hidden gems and unique local experiences that make your trip memorable.
Transportation Options
- Local Bus Service: The region offers reliable local bus routes that connect key areas, making it easy for you to explore without a car.
- Car Rentals: Renting a vehicle here provides the flexibility to visit scenic spots and hidden gems at your own pace within this coastal destination.
- Taxis and Rideshare Services: Taxis and popular rideshare options are readily available, offering convenient transportation for quick trips or when arriving from nearby airports.
- Water Transportation: Given the area's proximity to water, ferries and boat charters can be an enjoyable way to experience the region’s scenic waterfront views.
Local Customs Options
- Crab Feast Celebrations: Participating in the regional crab feasts is a cherished tradition, where locals gather to enjoy fresh Chesapeake Bay blue crabs with friends and family.
- Boat Building and Maritime Heritage: You’ll notice a strong maritime influence here, as boat building and seafaring skills are an integral part of the area's cultural identity.
- Historical Shoreline Festivals: The region hosts festivals that celebrate its rich history along the Chesapeake Bay, highlighting the area's past and community spirit.
- Southern Hospitality and Folk Traditions: Expect warm welcomes and traditional Southern hospitality, often expressed through local music, storytelling, and community gatherings.
Frequently Asked Questions About Calvert County?
1. What are the top vacation rentals in Calvert County?
There are a lot of options in Calvert County. If you plan on staying in the Calvert County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Calvert County:
- Waterfront Cabin with Million Dollar View and Luxury Bath! Find Shark's Teeth!
- Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
- Waterfront Wildlife Retreat on the Patuxent River
- Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
- Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.
- Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
- A breathtaking secluded luxury waterfront cottage, complete with a private pier.
- The Blue Crab Beach House - Free beach passes
- Bay view from Calvert Cliffs, Solomons Island & State Park nearby
- Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
2. How many vacation rentals have private pools in Calvert County?
There are 4 vacation rentals with private pools near Calvert County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Calvert County are best for families?
If you are looking for a family-friendly vacation home in Calvert County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Calvert County:
4. How many Rentbyowner vacation rentals are available in Calvert County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 252 in the Calvert County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Calvert County.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property, so it's best to review the specific listing details or contact the property owner directly to understand their terms and any potential fees.
6. How do I find the most suitable vacation rental in Calvert County?
You can filter your search based on preferences such as size, amenities, and location within the region. Reading reviews and contacting hosts can also help ensure you select the best option for your stay.
7. Are there any additional fees I should be aware of before booking?
Additional fees like cleaning, service charges, or taxes are typically outlined on the listing page. Be sure to review these details carefully or ask the host if anything is unclear.
8. What should I know about checking in and check-out procedures?
Check-in and check-out times, along with specific instructions, are provided in each listing. Contact the property owner if you need any assistance or have special requests.
9. Is it safe to book vacation rentals here during peak seasons?
Yes, many travelers find this destination to be very accommodating during peak times. Always verify the credibility of the listing and communicate directly with the host to ensure a secure and pleasant stay.
Calvert County Top Rated Vacation Rentals
1250 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
AU $304/Night
For 7 Nights AU $2,131
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Pool
- Ocean View
AU $555/Night
For 7 Nights AU $3,886
2000 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
AU $556/Night
For 7 Nights AU $3,890
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Pool
- Kitchen
AU $567/Night
For 7 Nights AU $3,968
8 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $1,006/Night
For 7 Nights AU $7,045
2000 ft²
11 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Private Pool
- Pool
- Balcony/Terrace
AU $712/Night
For 7 Nights AU $4,982
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
AU $194/Night
For 7 Nights AU $1,356
308.12 ft²
24 Guests
8 Bathrooms
Free Cancellation
Resort
- Private Pool
- Oceanfront
- Fireplace/Heating
AU $590/Night
For 7 Nights AU $4,127
