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, (41 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 ¥21,190
¥46,087 total
includes taxes & fees
Mar 10 - Mar 11
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 ¥26,997
¥51,200 total
includes taxes & fees
Mar 8 - Mar 9
Kentigern Shed at Scotland Yards

Easthaven: Game-Theme Waterfront+Boats+Fireplace

Easthaven: Game-Theme Waterfront+Boats+Fireplace
Montross
10.0 out of 10, Exceptional, (30 reviews)
"Great spot"
United States
SHAWN W.
The price is ¥32,208
¥75,370 total
includes taxes & fees
Mar 8 - Mar 9
Easthaven: Game-Theme Waterfront+Boats+Fireplace

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 ¥41,673
¥49,830 total
includes taxes & fees
Mar 6 - Mar 7
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 ¥31,235
¥63,437 total
includes taxes & fees
Mar 8 - Mar 9
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 ¥41,800
¥58,822 total
includes taxes & fees
Mar 6 - Mar 7
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 ¥54,936
¥122,201 total
includes taxes & fees
Mar 8 - Mar 9
4-BR Waterfront Turret Home

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 ¥42,379
¥51,410 total
includes taxes & fees
Mar 6 - Mar 7
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is ¥37,670
¥46,450 total
includes taxes & fees
Mar 6 - Mar 7
2 Bedroom Cottage at Coles Point Marina

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)
"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 ¥35,316
¥85,818 total
includes taxes & fees
Mar 10 - Mar 11
Anne & Fred`s Leonardtown Home W/ Arcade room!

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.
The price is ¥25,114
¥56,883 total
includes taxes & fees
Mar 16 - Mar 17
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

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.
The price is ¥21,033
¥68,823 total
includes taxes & fees
Mar 11 - Mar 12
Luxury Modern Waterfront Retreat

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 ¥29,822
¥68,466 total
includes taxes & fees
Mar 8 - Mar 9
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is ¥43,164
¥109,188 total
includes taxes & fees
Mar 16 - Mar 17
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

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 ¥27,261
¥74,914 total
includes taxes & fees
Mar 16 - Mar 17
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

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)
"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 ¥47,088
¥89,960 total
includes taxes & fees
Mar 8 - Mar 9
Charming Waterfront 3-bedroom house in Piney Point

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 ¥42,379
¥51,410 total
includes taxes & fees
Mar 6 - Mar 7
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 ¥51,797
¥130,054 total
includes taxes & fees
Mar 10 - Mar 11
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is ¥43,164
¥98,086 total
includes taxes & fees
Apr 2 - Apr 3
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.
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Top Callaway Hotel Reviews

Find out more about Callaway

Search for holiday rentals in Callaway on Expedia! You can easily find your home rentals, villas, holiday apartments in Callaway using one of the methods below:

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Look no further and take a look at our great range of rental properties in Callaway!

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?

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome! : 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. It offers a patio, a garden, and an arcade game room 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 Cecil's Old Mill and Patuxent River Naval Air Museum.

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.