Callaway Vacation Rentals

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Our top choices for Callaway vacation rentals

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (42 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 $172
CA $390 total
includes taxes & fees
Mar 25 - Mar 26
Soul Oasis - home on the Chesapeake Bay

Kentigern Shed at Scotland Yards

Kentigern Shed at Scotland Yards
Point Lookout
9.6 out of 10, Exceptional, (155 reviews)
"Nice place to stay and very enjoyable environment. Management team is excellent to handle the property. "
United States
william s.
The price is CA $236
CA $443 total
includes taxes & fees
Mar 27 - Mar 28
Kentigern Shed at Scotland Yards

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.
The price is CA $364
CA $440 total
includes taxes & fees
Mar 30 - Mar 31
Cottage Located on the Patuxent River!

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)
"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 CA $273
CA $559 total
includes taxes & fees
Mar 26 - Mar 27
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is CA $365
CA $514 total
includes taxes & fees
Apr 4 - Apr 5
Coles Point Marina

Dock+Kayaks+Firepit: Game Theme Waterfront Retreat

Dock+Kayaks+Firepit: Game Theme Waterfront Retreat
Montross
10.0 out of 10, Exceptional, (30 reviews)
"Great spot"
United States
SHAWN W.
The price is CA $285
CA $668 total
includes taxes & fees
Apr 14 - Apr 15
Dock+Kayaks+Firepit: Game Theme Waterfront Retreat

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 $371
CA $447 total
includes taxes & fees
Mar 29 - Mar 30
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

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)
"It was very comfortable felt like home "
United States
Carol S.
The price is CA $309
CA $771 total
includes taxes & fees
Mar 30 - Mar 31
Anne & Fred`s Leonardtown Home W/ Arcade room!

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is CA $329
CA $408 total
includes taxes & fees
Mar 30 - Mar 31
2 Bedroom Cottage at Coles Point Marina

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 $480
CA $1,082 total
includes taxes & fees
Mar 25 - Mar 26
4-BR Waterfront Turret Home

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, (5 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is CA $220
CA $503 total
includes taxes & fees
Mar 25 - Mar 26
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

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, (2 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is CA $261
CA $603 total
includes taxes & fees
Mar 25 - Mar 26
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

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 $236
CA $656 total
includes taxes & fees
Apr 6 - Apr 7
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

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 $328
CA $956 total
includes taxes & fees
Mar 30 - Mar 31
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, (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 $419
CA $801 total
includes taxes & fees
Mar 30 - Mar 31
Charming Waterfront 3-bedroom house in Piney Point

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is CA $340
CA $813 total
includes taxes & fees
Mar 30 - Mar 31
Come relax yourself a while

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 $371
CA $445 total
includes taxes & fees
Mar 25 - Mar 26
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

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 $453
CA $1,153 total
includes taxes & fees
Mar 25 - Mar 26
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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?

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR: This vacation home rental near Callaway offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable 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. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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.