Callaway Vacation Rentals

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Our top choices for Callaway vacation rentals

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is CA $377
CA $1,008 total
includes taxes & fees
Apr 20 - Apr 21
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is CA $326
CA $598 total
includes taxes & fees
Apr 21 - Apr 22
Coles Point Marina

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, (12 reviews)
"Pet friendly, easy check out, no cleaning involved."
United States
Naomi B.
The price is CA $322
CA $620 total
includes taxes & fees
Apr 24 - Apr 25
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is CA $400
CA $484 total
includes taxes & fees
Apr 20 - Apr 21
Cottage Located on the Patuxent River!

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.
The price is CA $370
CA $446 total
includes taxes & fees
Apr 21 - Apr 22
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (45 reviews)
"House was very nice and tidy and exactly as described. The host had a small binder full of helpful info including local restaurants and attractions. There was so much to do and everything was close bye. "
United States
Mindy V.
The price is CA $183
CA $401 total
includes taxes & fees
May 12 - May 13
Soul Oasis - home on the Chesapeake Bay

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.
The price is CA $479
CA $1,079 total
includes taxes & fees
Apr 20 - Apr 21
4-BR Waterfront Turret Home

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (127 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is CA $472
CA $585 total
includes taxes & fees
Apr 20 - Apr 21
2 Bedroom Cottage at Coles Point Marina

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (7 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is CA $253
CA $538 total
includes taxes & fees
Apr 20 - Apr 21
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully and tastefully decorated, immaculately clean, completely stocked top to bottom! You can tell by all of the details that these hosts care about curating a perfect stay for their guests. "
United States
Leslie K.
The price is CA $418
CA $804 total
includes taxes & fees
Apr 20 - Apr 21
Charming Waterfront 3-bedroom house in Piney Point

Luxury Modern Waterfront Retreat

Luxury Modern Waterfront Retreat
Montross
9.6 out of 10, Exceptional, (15 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is CA $209
CA $641 total
includes taxes & fees
Apr 22 - Apr 23
Luxury Modern Waterfront Retreat

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is CA $370
CA $446 total
includes taxes & fees
Apr 20 - Apr 21
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

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)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is CA $241
CA $663 total
includes taxes & fees
Apr 20 - Apr 21
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is CA $260
CA $602 total
includes taxes & fees
Apr 20 - Apr 21
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

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.
The price is CA $663
CA $1,393 total
includes taxes & fees
Apr 21 - Apr 22
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Dock+Boats+Firepit: Game Theme Waterfront Retreat

Dock+Boats+Firepit: Game Theme Waterfront Retreat
Montross
10.0 out of 10, Exceptional, (31 reviews)
"Great spot"
United States
SHAWN W.
The price is CA $340
CA $739 total
includes taxes & fees
Apr 22 - Apr 23
Dock+Boats+Firepit: Game Theme Waterfront Retreat

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is CA $339
CA $811 total
includes taxes & fees
Apr 27 - Apr 28
Come relax yourself a while

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

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is CA $308
CA $769 total
includes taxes & fees
Apr 20 - Apr 21
Anne & Fred`s Leonardtown Home W/ Arcade room!
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.
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Top Callaway Hotel Reviews

Find out more about Callaway

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Callaway. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Quaint waterfront home with private beach: This vacation home rental near Callaway is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a patio and a selection of games.

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 Cecil's Old Mill and Patuxent River Naval Air Station.

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.