Callaway Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Callaway holiday rentals

Exterior

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.
The price is HK$1,095
HK$2,238 total
includes taxes & fees
10 Mar - 11 Mar
Soul Oasis - home on the Chesapeake Bay
Dining

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.
The price is HK$1,006
HK$2,474 total
includes taxes & fees
17 Feb - 18 Feb
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Interior

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is HK$1,618
HK$4,104 total
includes taxes & fees
24 Feb - 25 Feb
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
TV

Waterfront Retreat | Sunset Views + Outdoor Lounge

Waterfront Retreat | Sunset Views + Outdoor Lounge
Leonardtown
The price is HK$1,032
HK$2,985 total
includes taxes & fees
16 Feb - 17 Feb
Waterfront Retreat | Sunset Views + Outdoor Lounge
Interior

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 HK$1,251
HK$2,842 total
includes taxes & fees
12 Feb - 13 Feb
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is HK$2,082
HK$2,930 total
includes taxes & fees
12 Feb - 13 Feb
Coles Point Marina
Fridge, microwave, oven, stovetop

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 HK$1,141
HK$3,556 total
includes taxes & fees
24 Feb - 25 Feb
Luxury Modern Waterfront Retreat
Sun-loungers

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 HK$2,075
HK$2,481 total
includes taxes & fees
17 Feb - 18 Feb
Cottage Located on the Patuxent River!
Sun-loungers, beach towels

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.
The price is HK$1,301
HK$3,661 total
includes taxes & fees
12 Feb - 13 Feb
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Living area

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is HK$1,876
HK$2,314 total
includes taxes & fees
12 Feb - 13 Feb
2 Bedroom Cottage at Coles Point Marina
Outdoor dining

Easthaven: Game-Theme Waterfront Retreat+Fireplace

Easthaven: Game-Theme Waterfront Retreat+Fireplace
Montross
10.0 out of 10, Exceptional, (30 reviews)
"Great spot"
United States
SHAWN W.
The price is HK$1,579
HK$3,700 total
includes taxes & fees
1 Mar - 2 Mar
Easthaven: Game-Theme Waterfront Retreat+Fireplace
Exterior

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.
The price is HK$2,345
HK$4,481 total
includes taxes & fees
12 Feb - 13 Feb
Charming Waterfront 3-bedroom house in Piney Point
TV, fireplace, video games, books

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 HK$2,579
HK$6,830 total
includes taxes & fees
24 Feb - 25 Feb
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Exterior

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 HK$2,110
HK$2,543 total
includes taxes & fees
13 Feb - 14 Feb
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fridge, microwave, oven, stovetop

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 HK$1,759
HK$4,247 total
includes taxes & fees
10 Mar - 11 Mar
Anne & Fred`s Leonardtown Home W/ Arcade room!
Smart TV, books

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 HK$2,735
HK$5,843 total
includes taxes & fees
24 Feb - 25 Feb
4-BR Waterfront Turret Home
Exterior

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 HK$2,110
HK$2,543 total
includes taxes & fees
19 Feb - 20 Feb
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Property grounds

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is HK$1,935
HK$4,589 total
includes taxes & fees
12 Feb - 13 Feb
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

Comfort Inn & Suites Lexington Park near Pax River

Comfort Inn & Suites Lexington Park near Pax River

10/10 Excellent
"Very nice place Very nice people!"
Renato 2-night trip
Posted 4 days ago
Comfort Inn & Suites Lexington Park near Pax River

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:

  • View our selection of featured holiday rentals in Callaway
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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 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?

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome! : This holiday home rental outside of Callaway is located on the beach, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and an arcade/games room 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 Museum and Patuxent River Naval Air Station.

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.