Callaway Vacation Rentals

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Oct 22 - Oct 23
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Oct 23 - Oct 24
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Oct 24 - Oct 26
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Oct 31 - Nov 2

Vacation Rentals in Callaway

Smart TV, books
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
9.6 out of 10, Exceptional, (7)
"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.
$333 nightly
The price is $368
Oct 24 - Oct 25
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Fridge, microwave, stovetop, coffee/tea maker
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
9.4 out of 10, Exceptional, (6)
"Great place to stay"
United States
Sherry R.
$156 nightly
The price is $172
Oct 24 - Oct 25
Total with taxes and fees
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Fridge, microwave, oven, stovetop
Riverside Dreams -golfcart-views-screened porch-
Riverside Dreams -golfcart-views-screened porch-
2.0 star property
10.0 out of 10, Exceptional, (3)
"We found the view and the accommodations quite lovely."
United States
Janet P.
$347 nightly
The price is $384
Oct 23 - Oct 24
Total with taxes and fees
Riverside Dreams -golfcart-views-screened porch-
Sun loungers, beach towels
Soul Oasis - home on the Chesapeake Bay
Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (35)
"Lovely house with tons of character. Clean and comfortable. A few steps from water. "
United States
Leah D.
$294 nightly
The price is $312
Oct 23 - Oct 24
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Fridge, microwave, oven, stovetop
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.
9.8 out of 10, Exceptional, (10)
"Property was very nice! Very clean and I especially loved the dual coffee maker!"
United States
Tamara G.
$282 nightly
The price is $303
Oct 23 - Oct 24
Total with taxes and fees
Waterfront home where you can relax or enjoy the things the Northern Neck.
House (3 Bedrooms) | Interior
Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks
Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks
3.0 star property
$655 nightly
The price is $727
Oct 26 - Oct 27
Total with taxes and fees
Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks
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
10.0 out of 10, Exceptional, (4)
"They thought of everything. I would definitely come back for another stay."
United States
Donna D.
$402 nightly
The price is $437
Oct 23 - Oct 24
Total with taxes and fees
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Outdoor dining
4 Bedroom Luxury Private Beach Retreat
4 Bedroom Luxury Private Beach Retreat
2.0 star property
$788 nightly
The price is $870
Nov 3 - Nov 4
Total with taxes and fees
4 Bedroom Luxury Private Beach Retreat
Interior
Fall Sale! Game Theme+Boats+Beach+King Bd+EV Chrgr
Fall Sale! Game Theme+Boats+Beach+King Bd+EV Chrgr
10.0 out of 10, Exceptional, (29)
"Great spot"
United States
SHAWN W.
$464 nightly
The price is $505
Oct 23 - Oct 24
Total with taxes and fees
Fall Sale! Game Theme+Boats+Beach+King Bd+EV Chrgr
Terrace/patio
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
10.0 out of 10, Exceptional, (4)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
$370 nightly
The price is $373
Oct 29 - Oct 30
Total with taxes and fees
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Interior
Waterfront Solomons Apartment
Waterfront Solomons Apartment
9.2 out of 10, Wonderful, (13)
"Very clean, awesome location and amazing hosts!! "
United States
Jeff R.
$254 nightly
The price is $269
Oct 23 - Oct 24
Total with taxes and fees
Waterfront Solomons Apartment
Terrace/patio
Charming Waterfront 3-bedroom house in Piney Point
Charming Waterfront 3-bedroom house 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.
$481 nightly
The price is $531
Nov 17 - Nov 18
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
TV, fireplace, table tennis
Anne & Fred`s Leonardtown Home W/ Arcade room!
Anne & Fred`s Leonardtown Home W/ Arcade room!
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.
$518 nightly
The price is $548
Oct 26 - Oct 27
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!
Fridge, microwave, oven, stovetop
Luxury Modern Waterfront Retreat
Luxury Modern Waterfront Retreat
9.6 out of 10, Exceptional, (14)
"My wife, daughter and I really enjoyed the serene and privacy of the property. The view of the lake and outdoors was beautiful. The home was clean and cozy and we plan to return. "
United States
Floyd H.
$456 nightly
The price is $496
Nov 4 - Nov 5
Total with taxes and fees
Luxury Modern Waterfront Retreat
Sun loungers
Cottage Located on the Patuxent River!
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
$300 nightly
The price is $317
Nov 1 - Nov 2
Total with taxes and fees
Cottage Located on the Patuxent River!
Exterior
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
10.0 out of 10, Exceptional, (11)
"Had such an enjoyable time over the weekend with the gracious hosts Peggy and Gary. Tidy and clean property in a beautiful area. Great food and great company. Definitely recommend for anyone looking for a nice peaceful getaway."
United States
Scott F.
$309 nightly
The price is $328
Oct 23 - Oct 24
Total with taxes and fees
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Exterior
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
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.
$309 nightly
The price is $328
Oct 23 - Oct 24
Total with taxes and fees
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Microwave, oven, stovetop, dishwasher
Roomy 6 bedroom home in the heart of Solomons, MD
Roomy 6 bedroom home in the heart of Solomons, MD
9.2 out of 10, Wonderful, (5)
"Stayed for business, completed our project and enjoyed some local eating spots. "
United States
Justin J.
$499 nightly
The price is $529
Nov 3 - Nov 4
Total with taxes and fees
Roomy 6 bedroom home in the heart of Solomons, MD
Exterior
Come relax yourself a while
Come relax yourself a while
$532 nightly
The price is $587
Oct 23 - Oct 24
Total with taxes and fees
Come relax yourself a while
Property grounds
Fun in the sun
Fun in the sun
2.0 out of 10, (1)
"This isnt a legitimate listing. The owner sold it over a year ago and never took it off the app. Also does not respond to help figure out/clean up the mess. I showed up to the rental to find a man living in it that they had sold the poperty to."
United States
Carl B.
$204 nightly
The price is $225
Oct 23 - Oct 24
Total with taxes and fees
Fun in the sun
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

The Inn at Leonardtown, an Ascend Collection Hotel

The Inn at Leonardtown, an Ascend Collection Hotel

10/10 Excellent
"Overall 10/10. Convenient area and nice building and room."
Sheldon 3-night trip
Posted 4 days ago
The Inn at Leonardtown, an Ascend Collection Hotel

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 $269 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.

Explore a world of travel with Expedia

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 Kinsale Museum, or get outside and enjoy nature at St. Mary's River State Park. In the larger area, you’ll find Patuxent River Naval Air Museum and Patuxent River Naval Air Station.

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.