Odyssey holiday homes, MD, USA: holiday houses & more

Scroll through and select from holiday rentals in Odyssey to find one that's perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, such as Wi-Fi and cable TV. What you'll find is a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Odyssey

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Sleeps 5 · 1 bedroom · 1 bathroom

House, pond, property. Private beach and Chesapeake Bay is behind far tree line.

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Sleeps 26 · 5 bedrooms · 3+ bathrooms

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Sleeps 8 · 3 bedrooms · 1+ bathroom

Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

Sleeps 16 · 6 bedrooms · 4+ bathrooms

View of firepit and waterfront (bring your own wood)

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Sleeps 14 · 5 bedrooms · 3 bathrooms

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

Book a holiday rental for your Odyssey getaway

Learn about the unique charm of Odyssey with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Odyssey

Do you want to find attractions to visit in the city? Venture out of your cosy holiday rental and experience everything that makes Odyssey a one-of-a-kind holiday spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Fridays Creek Winery (5.2 mi / 8.3 km)
Chesapeake Beach Water Park (6.3 mi / 10.1 km)
Lake Presidential Golf Club (8.8 mi / 14.2 km)
Renditions Golf Club (11.5 mi / 18.4 km)
South River Golf Links (12.4 mi / 19.9 km)
Six Flags America (13.7 mi / 22.1 km)

Exploring the natural landscape of Odyssey

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Odyssey is a great place to get outside. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

Upper Yough River (2 mi / 3.2 km)
Jug Bay Wetlands Sanctuary (4.2 mi / 6.8 km)
Shadyside Park (9.3 mi / 14.9 km)
Breezy Point Beach (10.6 mi / 17.1 km)
Triton Beach (12 mi / 19.4 km)
Old Maryland Farm (13.3 mi / 21.3 km)

Travelling to and around Odyssey

The nearest airport is in College Park, MD (CGS), located 22.6 mi (36.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Ronald Reagan National Airport (DCA), which is 23.3 mi (37.5 km) away.

Frequently asked questions

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

Different factors can affect how much you pay for a holiday home in Odyssey, including the type of property, season and length of stay. But, all of our holiday homes have something in common — amazing value. Just add your travel dates to find your ideal fit.

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

The average price for a holiday home near the beach in Odyssey depends on when you’re travelling and the style and size of property you’re searching for. You can find prices quickly and easily on Bookabach by entering your preferred travel dates and destination. Then use our filter tool to choose the number of bedrooms and amenities that you need, like air conditioning, WiFi and a pool.

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

The minimum age is usually 16, 18 or 21. It can vary from property to property on Bookabach, so check the rules of your preferred Odyssey stay before booking your trip.

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

It all depends on the Odyssey property. To view all available options offering extended stays, simply enter your dates and number of people into Bookabach. You can look forward to having the entire property to yourself, as well as comforts such as air conditioning, a kitchen and a backyard where your little ones can play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.