Georgetown, Chestertown holiday accommodation: short-term house rentals & properties

Scroll through and select from holiday rentals in Georgetown to find one that's perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you expect for your stay, which might include Wi-Fi and a pool. At the end of the day, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Find the best place to stay - Georgetown

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Sleeps 25 · 9 bedrooms · 6+ bathrooms

Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

Sleeps 16 · 6 bedrooms · 5+ bathrooms

Find spaces that suit your style

House

Condo/Apartment

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Georgetown getaway

Learn about the unique charm of Georgetown with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Georgetown

Do you want to discover top things to see and do during your stay? Venture out of your cosy holiday rental and check out everything that makes Georgetown a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

Rocky Point Golf Course (11.9 mi / 19.1 km)
Cassinelli Winery and Vineyards (12.2 mi / 19.6 km)
Hazel Miner Monument (14.1 mi / 22.6 km)
Crumpton Auction (15.1 mi / 24.3 km)

Exploring the natural landscape of Georgetown

Whether you're looking for adventure or just want to spend some time taking in the scenery, Georgetown is a great place to get out in nature. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

Miami Beach (11 mi / 17.7 km)
Rocky Point Park and Beach (11.4 mi / 18.4 km)
Betterton Beach (12.5 mi / 20.1 km)
Gunpowder Falls State Park (12.6 mi / 20.3 km)
North Point State Park (12.4 mi / 20 km)
Eastern Neck National Wildlife Refuge (13.3 mi / 21.4 km)

Transport to and around Georgetown

The nearest airport is in Baltimore, MD (MTN-Martin State), located 14.2 mi (22.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Baltimore Washington International Airport (BWI), which is 25.5 mi (41.1 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Georgetown?

The average price for a holiday home in Georgetown is based on several factors, such as property type, season and length of stay. Whether you're in search of a sprawling villa with a pool or a cosy cabin just for the two of you, just enter your dates of travel to see stays with fantastic value.

How much does it cost to rent a beach house in Georgetown?

The average price for a holiday home near the beach in Georgetown depends on when you're visiting the area and the style and size of property you want. You can easily find prices on Stayz by entering your travel dates and destination. Then use the handy filters to pick the number of bedrooms and amenities essential to you, like a pool, WiFi and air conditioning.

What are the top attractions for families in Georgetown?

Keep your kids occupied at these fun family-friendly attractions in Georgetown:

Historical Society of Kent County Maryland
River Arts Chestertown
Rolphs Wharf Marina

How old do you have to be to rent a holiday home in Georgetown?

The minimum age requirements can differ across properties on Stayz, so check the rules of the holiday home in Georgetown you're considering. But in general, it's 16, 18 or 21.

How long can I rent a holiday home in Georgetown for?

The amount of time you can book a Georgetown holiday home for varies depending on the property. Simply enter your travel dates to find available options offering extended stays. They have all the things you need to make your extended break more enjoyable and convenient, such as kitchens and laundries. Some Stayz holiday properties may also offer discounted weekly or monthly prices, so you can stay even longer for less.