Callaway Vacation Rentals

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Our top choices for Callaway vacation rentals

9.8 out of 10, Exceptional, (40 reviews)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
$252 nightly
The price is $267
Jan 12 - Jan 13
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
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.
$287 nightly
The price is $317
Jan 11 - Jan 12
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
10.0 out of 10, Exceptional, (11 reviews)
"Property was very nice! Very clean and I especially loved the dual coffee maker!"
United States
Tamara G.
$253 nightly
The price is $271
Jan 11 - Jan 12
Total with taxes and fees
Waterfront home where you can relax or enjoy the things the Northern Neck.

Vacation Home in Montross

Luxury Modern Waterfront Retreat
9.6 out of 10, Exceptional, (14 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
$384 nightly
The price is $418
Jan 11 - Jan 12
Total with taxes and fees
Luxury Modern Waterfront Retreat

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42 reviews)
"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.
$299 nightly
The price is $316
Jan 11 - Jan 12
Total with taxes and fees
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (5 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
$333 nightly
The price is $335
Feb 10 - Feb 11
Total with taxes and fees
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

Cabin in Hague

Coles Point Marina
2.0 star property
$344 nightly
The price is $375
Jan 11 - Jan 12
Total with taxes and fees
Coles Point Marina
2.0 star property
$245 nightly
The price is $260
Jan 11 - Jan 12
Total with taxes and fees
Back Creek Villa Open Deck Solomons Island Maryland
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.
$308 nightly
The price is $326
Jan 11 - Jan 12
Total with taxes and fees
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
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.
$374 nightly
The price is $407
Jan 13 - Jan 14
Total with taxes and fees
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
10.0 out of 10, Exceptional, (30 reviews)
"Great spot"
United States
SHAWN W.
$424 nightly
The price is $461
Jan 11 - Jan 12
Total with taxes and fees
MLK Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar

Vacation Home in Leonardtown

Potomac Vista Cottage
2.0 star property
$389 nightly
The price is $392
Jan 11 - Jan 12
Total with taxes and fees
Potomac Vista Cottage
3.0 star property
$754 nightly
The price is $837
Jan 11 - Jan 12
Total with taxes and fees
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
2.0 star property
$267 nightly
The price is $291
Jan 11 - Jan 12
Total with taxes and fees
2 Bedroom Cottage at Coles Point Marina

Vacation Home in Solomons

4-BR Waterfront Turret Home
2.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$647 nightly
The price is $716
Jan 11 - Jan 12
Total with taxes and fees
4-BR Waterfront Turret Home
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.
$519 nightly
The price is $573
Jan 11 - Jan 12
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
9.2 out of 10, Wonderful, (5 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.
$538 nightly
The price is $570
Jan 11 - Jan 12
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
$868 nightly
The price is $874
Jan 13 - Jan 14
Total with taxes and fees
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Apartment in Mechanicsville

Come relax yourself a while
$532 nightly
The price is $587
Jan 11 - Jan 12
Total with taxes and fees
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 vacation rentals

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

Callaway vacation 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 low season months. For more hustle and bustle, you may prefer to visit Callaway in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $267 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Callaway rentals

At Expedia, we put the best Callaway vacation 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 vacation.

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 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?

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp: This vacation home rental near Callaway is located on the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 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.