Callaway Holiday Rentals

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Our top choices for Callaway holiday rentals

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
9.8 out of 10, Exceptional, (40)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is NZ$489
includes taxes & fees
4 Jan - 5 Jan 2026
Soul Oasis - home on the Chesapeake Bay

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, (9)
"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 NZ$543
includes taxes & fees
4 Jan - 5 Jan 2026
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, (42)
"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "
United States
RACHEL S.
The price is NZ$547
includes taxes & fees
5 Jan - 6 Jan 2026
Cottage Located on the Patuxent River!

Waterfront home where you can relax or enjoy the things the Northern Neck.

Waterfront home where you can relax or enjoy the things the Northern Neck.
Lottsburg
10.0 out of 10, Exceptional, (11)
"Property was very nice! Very clean and I especially loved the dual coffee maker!"
United States
Tamara G.
The price is NZ$473
includes taxes & fees
4 Jan - 5 Jan 2026
Waterfront home where you can relax or enjoy the things the Northern Neck.

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)
"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 NZ$564
includes taxes & fees
1 Jan - 2 Jan 2026
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar

Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar
Montross
10.0 out of 10, Exceptional, (30)
"Great spot"
United States
SHAWN W.
The price is NZ$794
includes taxes & fees
6 Jan - 7 Jan 2026
Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar

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)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Port Republic
9.4 out of 10, Exceptional, (6)
"Great place to stay for a getaway "
United States
Adam W.
The price is NZ$304
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
2.0 star property
Solomons
10.0 out of 10, Exceptional, (7)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is NZ$1,293
includes taxes & fees
1 Jan - 2 Jan 2026
4-BR Waterfront Turret Home

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is NZ$1,558
includes taxes & fees
4 Jan - 5 Jan 2026
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Luxury Modern Waterfront Retreat

Luxury Modern Waterfront Retreat
Montross
9.6 out of 10, Exceptional, (14)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is NZ$755
includes taxes & fees
6 Jan - 7 Jan 2026
Luxury Modern Waterfront Retreat

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)
"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 NZ$978
includes taxes & fees
1 Jan - 2 Jan 2026
Charming Waterfront 3-bedroom house in Piney Point

Potomac Vista Cottage

Potomac Vista Cottage
2.0 star property
Leonardtown
The price is NZ$661
includes taxes & fees
6 Jan - 7 Jan 2026
Potomac Vista Cottage

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)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is NZ$1,505
includes taxes & fees
6 Jan - 7 Jan 2026
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

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

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (5)
"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 NZ$997
includes taxes & fees
11 Jan - 12 Jan 2026
Anne & Fred`s Leonardtown Home W/ Arcade room!

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is NZ$1,011
includes taxes & fees
8 Jan - 9 Jan 2026
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

Everything you need to know about Callaway holiday rentals

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

Callaway holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Callaway holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Callaway holiday rentals we have selected for you start as low as NZ$489 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Callaway rentals

At Expedia, we put the best Callaway holiday 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 holiday.

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 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?

Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar: This holiday home rental outside of Callaway is located on the beach, and has a fireplace, a patio 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. Kick off your shoes and enjoy yourself with a garden 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 wider area, you’ll find Cecil's Old Mill and Patuxent River Naval Air Museum.

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.