Callaway Holiday Rentals

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Holiday Rentals in Callaway

Cottage in Lusby

9.8 out of 10, Exceptional, (37)
"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 AU$411
includes taxes & fees
15 Dec - 16 Dec
Soul Oasis - home on the Chesapeake Bay

Cottage in Point Lookout

9.4 out of 10, Exceptional, (8)
"The house was close to family in the area, so location was great. The house was clean and airy. The door lock was a bit tricky - otherwise all was excellent."
United States
Marc C.
The price is AU$567
includes taxes & fees
8 Dec - 9 Dec
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Holiday Home in Solomons

2.0 star property
10.0 out of 10, Exceptional, (7)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
United States
Rudy L.
The price is AU$1,044
includes taxes & fees
14 Dec - 15 Dec
4-BR Waterfront Turret Home

Cottage in Prince Frederick

10.0 out of 10, Exceptional, (42)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is AU$490
includes taxes & fees
3 Dec - 4 Dec
Cottage Located on the Patuxent River!

Holiday Home in 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 AU$467
includes taxes & fees
3 Dec - 4 Dec
Waterfront home where you can relax or enjoy the things the Northern Neck.

Apartment in Port Republic

9.4 out of 10, Exceptional, (6)
"Great place to stay"
United States
Sherry R.
The price is AU$266
includes taxes & fees
15 Dec - 16 Dec
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Cottage in Lusby

3.0 star property
The price is AU$1,175
includes taxes & fees
3 Dec - 4 Dec
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Holiday Home in Montross

9.6 out of 10, Exceptional, (14)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is AU$749
includes taxes & fees
3 Dec - 4 Dec
Luxury Modern Waterfront Retreat

Holiday Home in Montross

10.0 out of 10, Exceptional, (29)
"Comfy, relaxing, beautiful, relaxing vacation home. We went to unwind and the facilities and owners were a delight. Kitchen was super well stocked with everything needed to handle meals for 11 people. Popcorn was a smash. The front door unlocked with our code and we were all ready to expand and kick off 9 days together."
United States
Al F.
The price is AU$711
includes taxes & fees
7 Dec - 8 Dec
Game Themed Fun! Boats+Beach+King Bd+EV Chrgr

Holiday Home in 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 AU$884
includes taxes & fees
3 Dec - 4 Dec
Charming Waterfront 3-bedroom house in Piney Point

Holiday Home in Solomons

9.6 out of 10, Exceptional, (8)
"Stayed for business, completed our project and enjoyed some local eating spots. "
United States
Justin J.
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Holiday Home in Point Lookout

9.6 out of 10, Exceptional, (155)
"Nice place to stay and very enjoyable environment. Management team is excellent to handle the property. "
United States
william s.
The price is AU$524
includes taxes & fees
3 Dec - 4 Dec
Kentigern Shed at Scotland Yards

Holiday Home in Fishing Creek

10.0 out of 10, Exceptional, (11)
"My best friend and I spent a weekend at the lodge and had a wonderful time. We were welcomed by Debbie and she gave us a nice tour of the place. We love sea glass hunting and there is a great spot not far from the lodge where we found TONS. I also found shark teeth! The lodge was very clean, unique, and in a beautiful location. We can't wait to come back with our husbands!"
United States
Ashley F.
The price is AU$506
includes taxes & fees
11 Dec - 12 Dec
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Holiday Home in Fishing Creek

10.0 out of 10, Exceptional, (1)
"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 AU$506
includes taxes & fees
3 Dec - 4 Dec
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Apartment in Solomons

9.0 out of 10, Wonderful, (14)
"Nice little place to stay"
United States
Eric S.
Peaceful Waterfront Apartment in the Heart of Solomons Island

Apartment in 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 AU$894
includes taxes & fees
3 Dec - 4 Dec
Anne & Fred`s Leonardtown Home W/ Arcade room!

Holiday Home in Lexington Park

2.0 star property
The price is AU$280
includes taxes & fees
7 Dec - 8 Dec
Peaceful tiny home Saltara where you can realx and unwind

Holiday Home in Point Lookout

2.0 star property
10.0 out of 10, Exceptional, (1)
Luxury 4-Bedroom Waterfront Beachfront Home with Bay Views & Spa

Apartment in Mechanicsville

The price is AU$905
includes taxes & fees
3 Dec - 4 Dec
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 favourite 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 depend 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 AU$411 per night. Entering your travel dates in the search wizard might find you 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?

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp: This holiday home rental outside of Callaway is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 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.