Photo by Ronanne Vinson

Calvert County holiday rentals

We found 296 holiday rentals — enter your dates for availability
Select from 121 homes, 31 cottages and other holiday rentals in Calvert County to find one that's perfect for your trip. Holiday rentals offer the best amenities for your family, friends or furry companion, such as a pool and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Popular Calvert County destinations on Stayz

Holiday rentals with weekly discounts – Calvert County

Showing deals for:18 Dec - 25 Dec

Dining
Property grounds
Exterior
Marina
Exceptional
(9 reviews)

Houseboat on Solomons Island

Solomons

8% off
AU$3,121
for 7 nights, 1 houseboat
AU$446 per night
includes taxes & fees
Houseboat on Solomons Island
Exterior
Dining
Living area
Terrace/patio
Exceptional
(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
AU$5,451
for 7 nights, 1 home
AU$779 per night
includes taxes & fees
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Convenient open-concept design: kitchen, dining and living areas
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Exceptional
(163 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
AU$3,312
for 7 nights, 1 home
AU$473 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Dining room showing steps to loft. Dining room seats 8-10
French doors from kitchen go to backyard wrap-around deck
Ariel view of the house, pool, dock, lagoon and beautiful Chesapeake Bay.
View of the lagoon and Chesapeake bay from the living room.
Wonderful
(21 reviews)

Serenity Bay-Spacious House-Prv Pool-6 bdrms-5baths-Hot Tub-AskAbout 2NightStays

Lexington Park

5% off
AU$7,219
for 7 nights, 1 home
AU$1,031 per night
includes taxes & fees
Serenity Bay-Spacious House-Prv Pool-6 bdrms-5baths-Hot Tub-AskAbout 2NightStays
Dining
Exterior
Living area
Private kitchen
Exceptional
(25 reviews)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman Island

8% off
AU$4,056
for 7 nights, 1 cottage
AU$579 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Living area
Outdoor dining
Exterior detail
Property grounds
Exceptional
(11 reviews)

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck

Huntingtown

8% off
AU$5,023
for 7 nights, 1 cottage
AU$718 per night
includes taxes & fees
Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
Property grounds
Exterior
Dining
Living area
Wonderful
(17 reviews)

Magnificent Water Front Property

Solomons

7% off
AU$7,906
for 7 nights, 1 home
AU$1,129 per night
includes taxes & fees
Magnificent Water Front Property
Directly next door to Sunrise Garden park
Beautiful North Beach, MD
Open-concept living area and kitchen
Beautiful views from your own private balcony!
Exceptional
(21 reviews)

Unbelievable beach views for 6

North Beach

8% off
AU$3,617
for 7 nights, 1 apartment
AU$517 per night
includes taxes & fees
Unbelievable beach views for 6
Beach
Property grounds
Room
Interior
Wonderful
(15 reviews)

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict

8% off
AU$2,269
for 7 nights, 1 cottage
AU$324 per night
includes taxes & fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
steps to the loft
entryway
Exterior
dining area
Exceptional
(61 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off
AU$1,857
for 7 nights, 1 cottage
AU$265 per night
includes taxes & fees
Soul Oasis - home on the Chesapeake Bay
Exterior
Living area
Private kitchen
Dining
Exceptional
(7 reviews)

Waterfront- 5-bedroom house with dock in charming North Beach

North Beach

8% off
AU$10,883
for 7 nights, 1 home
AU$1,555 per night
includes taxes & fees
Waterfront- 5-bedroom house with dock in charming North Beach
Living Room into Kitchen/Dining
Foyer into Living Room
Foyer with stairs to second floor peak into 1st floor master bedroom
Kitchen/dining
Exceptional
(91 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
AU$5,996
for 7 nights, 1 home
AU$857 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Life is good!
Every sunrise brings new hope for a brighter future.
Gather around the table for family dinner.
Star light, star bright, first star I see tonight.
Exceptional
(52 reviews)

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek

8% off
AU$2,771
for 7 nights, 1 cottage
AU$396 per night
includes taxes & fees
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Private kitchen
Room
Interior
Living area
Exceptional
(17 reviews)

Bay Charm. 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil!

Prince Frederick

8% off
AU$2,965
for 7 nights, 1 home
AU$424 per night
includes taxes & fees
Bay Charm. 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil!
Exterior
Outdoor dining
Exterior detail
Outdoor dining
Exceptional
(174 reviews)

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

St Leonard

6% off
AU$2,082
for 7 nights, 1 cottage
AU$297 per night
includes taxes & fees
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
Partial view of the water
Hilltop cottage December
Private kitchen
Open floor plan, dining table and sleep sofa
Exceptional
(30 reviews)

Quiet Woodland cottage near St. Leonard's Creek

Lusby

8% off
AU$1,350
for 7 nights, 1 cottage
AU$193 per night
includes taxes & fees
Quiet Woodland cottage near St. Leonard's Creek
Exterior
Foyer
Property grounds
Room
Exceptional
(27 reviews)

Guest Quarters at the Inn - 102

North Beach

8% off
AU$2,054
for 7 nights, 1 apartment
AU$293 per night
includes taxes & fees
Guest Quarters at the Inn - 102
Living room
Coffee, tea, cream, and sugar provided
Stairs leading to bedrooms
Side view
Exceptional
(16 reviews)

Two bedroom two bath home on charming Solomons Island

Solomons

8% off
AU$3,350
for 7 nights, 1 apartment
AU$479 per night
includes taxes & fees
Two bedroom two bath home on charming Solomons Island
Two bar stools are available at the kitchen bar.
The front porch has ceiling fans to help keep you cool.
Front room and steps to upstairs
Exterior
Exceptional
(57 reviews)

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

Fishing Creek

7% off
AU$1,890
for 7 nights, 1 home
AU$270 per night
includes taxes & fees
Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly
Marina
Interior
Interior
Interior
Exceptional
(55 reviews)

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

West River

12% off
AU$1,773
for 7 nights, 1 cottage
AU$253 per night
includes taxes & fees
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
View of parking pad 1 car is backed in and 1 for studio on the bay pulled in.
Living area
Exterior detail
Private kitchen
Exceptional
(31 reviews)

Studio on the Bay.

Saint Leonard

8% off
AU$1,740
for 7 nights, 1 apartment
AU$249 per night
includes taxes & fees
Studio on the Bay.
The deck is for your use
View from driveway
Interior
Kitchen is stocked with pots pans, dishes etc
Exceptional
(17 reviews)

Solomons Island with views of harbor!

Solomons

8% off
AU$2,115
for 7 nights, 1 apartment
AU$302 per night
includes taxes & fees
Solomons Island with views of harbor!
Living area
Foyer
Room
Exterior
Exceptional
(21 reviews)

Guest quarters at the inn - 205

North Beach

8% off
AU$2,479
for 7 nights, 1 apartment
AU$354 per night
includes taxes & fees
Guest quarters at the inn - 205
Room
Foyer
Bathroom
Exterior
Exceptional
(18 reviews)

Guest Quarters at the Inn - 101

North Beach

8% off
AU$2,054
for 7 nights, 1 apartment
AU$293 per night
includes taxes & fees
Guest Quarters at the Inn - 101

Choose a holiday rental for your Calvert County getaway

Learn about the unique charm of Calvert County with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Calvert County

Are you searching for attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Calvert County a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Running Hare Vineyard (5.3 mi / 8.5 km)
  • Chesapeake Beach Water Park (10.9 mi / 17.5 km)
  • Maryland International Raceway (18.8 mi / 30.2 km)
  • Budds Creek Motocross Park (18.8 mi / 30.3 km)
  • White Plains Golf Course (21.4 mi / 34.4 km)
  • Thanksgiving Farm Wines (23.7 mi / 38.2 km)

Exploring the natural landscape of Calvert County

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Calvert County is a great spot to appreciate mother nature. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Matoaka Beach (5.2 mi / 8.4 km)
  • Breezy Point Beach (6 mi / 9.7 km)
  • Flag Ponds Nature Park (6.9 mi / 11 km)
  • Cove Point Beach (13.1 mi / 21.1 km)
  • St. Mary's River State Park (18.9 mi / 30.5 km)
  • Blackwater National Wildlife Refuge (23.5 mi / 37.8 km)

Frequently asked questions

What is the best area to stay in Calvert County when booking a holiday home?
One of the more sought-after areas for a Calvert County holiday home is Rose Haven. When you book your Stayz holiday home, you can look forward to having the entire place to yourselves. This means you won't have to share it with anyone apart from your people.
What is the most popular type of holiday home accommodation in Calvert County?
Houses are the most popular type of holiday home in Calvert County, according to our data. Even if you've got something bigger or smaller in mind, Stayz has holiday homes in a variety of shapes and sizes. Explore our options to find your perfect fit.
How much does it cost to rent a holiday home in Calvert County?
The average price for a holiday home in Calvert County is determined by a number of factors, including property type, season and length of stay. Whether you'd like a sprawling villa with lots of space or a cosy cottage just enough for two, just add your dates of travel to view some great-value stays.
How much does it cost to rent a beach house in Calvert County?
When you travel and the size and style of the property will determine the cost of your beachside escape. Click on your Calvert County travel dates to see your options on Stayz. Can't live without a private pool? Use the filters to choose the features and amenities you need.
What are popular home amenities in Calvert County?
A microwave oven, a fridge and off-street parking options are rated the most popular home amenities in Calvert County. Whether you're taking a trip by yourself, with your better half or a group of family members, Stayz can help you find a holiday home that suits your tastes with a load of extras you'll love.
Are there large group holiday homes in Calvert County?
With eight properties that can host 10 or more guests in Calvert County, you won't have to hold back on your invites. From holidays with the extended family to special events like birthday and Christmas parties, Stayz can help you find a large group home to suit the occasion.
What are the top attractions for families in Calvert County?
Keeping the kiddos entertained during your stay in Calvert County is a snap with these family-friendly attractions:
  • Chesapeake Beach Water Park
  • Calvert Cliffs State Park
  • Breezy Point Beach
Can I find two-bedroom holiday homes in Calvert County?
Calvert County has 21 two-bedroom holiday homes for you to pick from. Find a holiday home with all the privacy and space you're looking for at an attractive price on Stayz.
Are there holiday homes with WiFi in Calvert County?
You'll find 52 holiday homes with WiFi in Calvert County. If you want to disconnect from the world during your escape, but still want to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Stayz.
How old do you have to be to rent a holiday home in Calvert County?
You should check with the Calvert County holiday home you want on Stayz as age restrictions differ. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Calvert County for?
The length of time you can book a holiday home in Calvert County depends on the property. Simply enter your selected dates to see a list of options offering extended stays. With plenty of amenities such as washing machines and kitchens, as well as some offering discounted weekly or monthly prices, you're sure to discover the perfect place to call your home away from home in Calvert County.

More holiday ideas