Callaway Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

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

Our top choices for Callaway vacation rentals

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
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.
$287 nightly
The price is $317
Jan 27 - Jan 28
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (41 reviews)
"The cozy cabin had everything needed for a comfortable stay. It was in a very private setting with the beach access a few houses away. You can hear the Chesapeake bay lapping at the shore and catch a glimpse of sail boats going by. We enjoyed our time at the home."
United States
Mary G.
$243 nightly
The price is $257
Jan 27 - Jan 28
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
$344 nightly
The price is $375
Jan 27 - Jan 28
Total with taxes and fees
Coles Point Marina

Easthaven | Game-Themed Waterfront Retreat

Easthaven | Game-Themed Waterfront Retreat
Montross
10.0 out of 10, Exceptional, (30 reviews)
"Great spot"
United States
SHAWN W.
$418 nightly
The price is $455
Feb 1 - Feb 2
Total with taxes and fees
Easthaven | Game-Themed Waterfront Retreat

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (42 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
$300 nightly
The price is $317
Jan 27 - Jan 28
Total with taxes and fees
Cottage Located on the Patuxent River!

Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Lexington Park
10.0 out of 10, Exceptional, (5 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
$361 nightly
The price is $363
Feb 2 - Feb 3
Total with taxes and fees
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
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.
$307 nightly
The price is $325
Jan 27 - Jan 28
Total with taxes and fees
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Potomac Vista Cottage

Potomac Vista Cottage
Leonardtown
$351 nightly
The price is $353
Jan 27 - Jan 28
Total with taxes and fees
Potomac Vista Cottage

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Montross
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.
$370 nightly
The price is $403
Jan 27 - Jan 28
Total with taxes and fees
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Luxury Modern Waterfront Retreat

Luxury Modern Waterfront Retreat
Montross
9.6 out of 10, Exceptional, (14 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
$418 nightly
The price is $455
Feb 1 - Feb 2
Total with taxes and fees
Luxury Modern Waterfront Retreat

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
$267 nightly
The price is $291
Jan 27 - Jan 28
Total with taxes and fees
2 Bedroom Cottage at Coles Point Marina

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
$754 nightly
The price is $837
Jan 27 - Jan 28
Total with taxes and fees
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
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.
$522 nightly
The price is $576
Jan 27 - Jan 28
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point

Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
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.
$547 nightly
The price is $579
Jan 27 - Jan 28
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$677 nightly
The price is $748
Jan 27 - Jan 28
Total with taxes and fees
4-BR Waterfront Turret Home

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
$868 nightly
The price is $874
Jan 27 - Jan 28
Total with taxes and fees
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Come relax yourself a while

Come relax yourself a while
Mechanicsville
$532 nightly
The price is $587
Jan 27 - Jan 28
Total with taxes and fees
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Callaway vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Callaway vacation 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 low season months. For more hustle and bustle, you may prefer to visit Callaway in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $257 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Callaway rentals

At Expedia, we put the best Callaway vacation 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 vacation.

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 vacation rental in Callaway?

Yes, we have vacation rentals close to popular points of interest in Callaway, or you can select a more secluded option if you want a relaxing place to stay.

What's the top vacation rental that Callaway has to offer?

All Year Retreat - Indoor Heated Pool, Beach, Game & Movie Cottage, Sleeps 21: This vacation home rental near Callaway is located on a river and has an indoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 larger area, you’ll find Patuxent River Naval Air Station and St. Mary's College of Maryland.

What’s a vacation rental in Callaway like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Callaway. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.