Callaway Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Callaway holiday rentals

9.8 out of 10, Exceptional, (40 reviews)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is AU$414
includes taxes & fees
25 Jan - 26 Jan
Soul Oasis - home on the Chesapeake Bay
9.4 out of 10, Exceptional, (10 reviews)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
The price is AU$477
includes taxes & fees
19 Jan - 20 Jan
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42 reviews)
"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "
United States
RACHEL S.
The price is AU$478
includes taxes & fees
19 Jan - 20 Jan
Cottage Located on the Patuxent River!

Cabin in Hague

Coles Point Marina
2.0 star property
The price is AU$561
includes taxes & fees
19 Jan - 20 Jan
Coles Point Marina
10.0 out of 10, Exceptional, (5 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is AU$536
includes taxes & fees
2 Feb - 3 Feb
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is AU$487
includes taxes & fees
19 Jan - 20 Jan
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Holiday Home in Montross

Luxury Modern Waterfront Retreat
9.6 out of 10, Exceptional, (14 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is AU$606
includes taxes & fees
20 Jan - 21 Jan
Luxury Modern Waterfront Retreat

Holiday Home in Leonardtown

Potomac Vista Cottage
2.0 star property
The price is AU$521
includes taxes & fees
19 Jan - 20 Jan
Potomac Vista Cottage
10.0 out of 10, Exceptional, (30 reviews)
"Great spot"
United States
SHAWN W.
The price is AU$679
includes taxes & fees
19 Jan - 20 Jan
Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar
2.0 star property
The price is AU$433
includes taxes & fees
19 Jan - 20 Jan
2 Bedroom Cottage at Coles Point Marina
3.0 star property
The price is AU$1,253
includes taxes & fees
19 Jan - 20 Jan
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed this house fully for our Thanksgiving stay! We even took the canoes out for a spin. Nice walks around the development and the beach area is lovely. "
United States
Julie I.
The price is AU$600
includes taxes & fees
19 Jan - 20 Jan
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
10.0 out of 10, Exceptional, (1 review)
"Beautiful newly renovated space with all new appliances, furniture and kitchenware. Comfortable beds, and super clean rooms. Large outside area with new Weber grill, fire pit, and three kayaks. Nice easy to access dock. "
United States
Kit C.
The price is AU$861
includes taxes & fees
20 Jan - 21 Jan
Charming Waterfront 3-bedroom house in Piney Point

Holiday Home in Solomons

4-BR Waterfront Turret Home
2.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is AU$1,095
includes taxes & fees
21 Jan - 22 Jan
4-BR Waterfront Turret Home
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is AU$1,301
includes taxes & fees
20 Jan - 21 Jan
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
9.2 out of 10, Wonderful, (5 reviews)
"Nice place to stay. Perfect location for our needs. Suggest noting the hot and cold water flip upstairs, and to add a mirror in the hallway by outlet for blow dryer."
United States
Lauren A.
The price is AU$869
includes taxes & fees
19 Jan - 20 Jan
Anne & Fred`s Leonardtown Home W/ Arcade room!

Apartment in Mechanicsville

Come relax yourself a while
The price is AU$882
includes taxes & fees
19 Jan - 20 Jan
Come relax yourself a while
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Callaway Hotel Reviews

Find out more about Callaway

Everything you need to know about Callaway holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Callaway holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Callaway holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Callaway holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Callaway. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Callaway holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Callaway holiday rentals we have selected for you start as low as AU$414 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Callaway rentals

At Expedia, we put the best Callaway holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Callaway rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Callaway holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Callaway. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Callaway?

Yes, there are holiday rentals close to the most popular sights in Callaway, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Callaway has to offer?

All Year Retreat - Indoor Heated Pool, Beach, Game & Movie Cottage, Sleeps 21: This holiday home rental outside of Callaway is located on a river, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, so that you can cook with friends or family. It offers a patio, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Callaway?

While exploring the area, visit family-friendly sights like Michael P. O'Brien Athletics and Recreation Center, or get outside and enjoy nature at St. Mary's River State Park. In the wider area, you’ll find Patuxent River Naval Air Station and St. Mary's College of Maryland.

What’s a holiday rental in Callaway like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Callaway. Holiday rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.