Callaway Vacation Rentals from $278: Search Short-Term Rentals

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Our top choices for Callaway vacation rentals

A single-story house with a front porch, a small deck, and a number '4' on the side.

1. Coles Point Marina

Hague

$255 nightly

Oct 14 - Oct 15

Total with taxes and fees

A covered patio with a view of a lake, furnished with chairs and a table.

2. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Lexington Park

Andrea B.

$406 nightly

Oct 20 - Oct 21

Total with taxes and fees

A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

3. 2 Acre Oasis with Private Beach! Family and dog friendly!

Leonardtown

J B.

$767 nightly

Oct 26 - Oct 27

Total with taxes and fees

A room with a large window overlooking a beach with a wooden pier and lounge chairs.

4. Cozy Virginia Potomac Riverfront Cottage

Hague

Natt L.

$315 nightly

Oct 14 - Oct 15

Total with taxes and fees

A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

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

Leonardtown

Christy C.

$548 nightly

Oct 14 - Oct 15

Total with taxes and fees

A two-story house with a balcony, surrounded by trees and a wooden fence.

6. Charming Waterfront 3-bedroom house in Piney Point

Piney Point

Meira

$676 nightly

Oct 30 - Oct 31

Total with taxes and fees

A spacious living room with a large sofa, a television, and a view of the ocean.

7. 4-BR Waterfront Turret Home

Solomons

Thomas S.

$665 nightly

Oct 14 - Oct 15

Total with taxes and fees

A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

8. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Lusby

Nicholas L.

$971 nightly

Oct 14 - Oct 15

Total with taxes and fees

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Top Callaway Hotel Reviews

Spark by Hilton California Lexington Park

10/10 Excellent

"I had a wonderful experience. The room was clean and the breakfast was nice. There is coffee available 24/7 and it was also very good. The staff were kind and friendly. Overall I had a wonderful experience."

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

10/10 Excellent

"We've been coming here for 3yrs now for our annual girlfriend getaway, and it has become one of our favorite traditions! This is the perfect place for a quiet girls' weekend... peaceful, beautiful, relaxing, and right on the Potomac River. The setting is absolutely wonderful, and the home gives us the perfect space to slow down, catch up, and laugh, and enjoy time together. And the owner is truly wonderful. She is incredibly easy to communicate with, thoughtful, and always so accommodating. We can't wait to stay here again and highly recommend this rental to anyone looking for a relaxing and beautiful getaway on the Potomac!"

Quality Inn Solomons - Beacon Marina

8/10 Good

"Everything was good, standard hotel/motel stuff: little coffee pot, mini-fridge, microwave, tv,a/c - everything worked as expected, furniture, carpeting, lights, bathroom all looked newish and everything was very clean. Desk folk were pleasant, didn’t have much interaction. The big plus is the location, right by a huge marina (if you like looking at boats) and the Calvert Marine Museum- combines natural history and the commercial history of the area, has the Drum Point lighthouse (you can tour) and a boat tour of Patuxent Harbor, plus fossils, river otters, fish. Calvert Cliffs / Flag Pond parks are a 10 minute drive if you want to dig for fossils yourself. So: comfortable place, very reasonably priced, close to all sorts of stuff; definitely worth it."

Belle of the Chesapeake Bay

10/10 Excellent

"This house was perfect for a short summer getaway with our family, including our 2 grandkids! The beds were super comfortable and the layout of the house worked perfectly for two couples and a family of 4. The boardwalk in Solomons was lovely with beautiful sunsets. We loved the outdoor sculpture garden, the Calvert State Park cliffs by the beach and the awesome mariners museum. The food at the Pier was outstanding, as was the ice cream shop next to the bait and tackle place down the street. All in all, this was a great visit! Glad we found this house to accommodate us so well!"

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

8/10 Good

"The Bay Estate is an absolute gorgeous property. However, host was not good at communicating and CLEANING CREWS NEED TO DO BETTER JOB!We had 11 mo old and 16 mo old babies with us; on day one, crawling and walking on the floors turned their knees/feet brown; the floors need a good mopping. The grill/sink and outdoor area was filthy, sent pictures to host, no remedy.The conservatory waterfall was not operating; asked if it could be turned on, no response. Plants in conservatory in desperate need of water and dead leaves need to be cleaned up. There is a steady drip in pipe in conservatory. Told host, no remedy.We couldn't locate a carafe for drip Cuisinart coffee maker. Host said they would check but we didn't hear back. When we arrived on Monday, 7/20, the 3 trash bins by the gate were full, when departing on Friday 7/24, the 3 bins were still full. We reached out to host asking what we were supposed to do with garbage, they stated garbage pickup is Friday and they would be back in touch on what we needed to do if they weren't empty Friday when we checked out. We did not hear from them so we left bags by bins. There were no kayaks on property as stated in information; if you are not going to provide kayaks, take them off your information.We replaced batteries in 2 of the tv remotes.THE BAY ESTATE IS A BEAUTIFUL PROPERTY (kitchen appliances are high quality, enormous kitchen table is a huge plus for large groups). Issues we had can be easily remedied."

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

10/10 Excellent

"This was a return trip for me, as always the property was clean, comfortable, quiet, The communication with the host was excellent, and we’ll definitely be back in the future to enjoy the gem that Hoopers Island is. Thank you for sharing your property again."

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 $278 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?

3-bedroom house in soothing Saint Leonard with AC for relaxing stays: This vacation home rental near Callaway offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

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 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.

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Check prices for these dates

Our top choices for Callaway vacation rentals

1. Coles Point Marina

2. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

3. 2 Acre Oasis with Private Beach! Family and dog friendly!

4. Cozy Virginia Potomac Riverfront Cottage

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

6. Charming Waterfront 3-bedroom house in Piney Point

7. 4-BR Waterfront Turret Home

8. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

9. Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK

10. 2 Bedroom Cottage at Coles Point Marina

11. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

12. Lakefront Cabin Near Solomons Island w/ Hot Tub

13. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

14. Waterfront Reset: Views, Games, Boats & Total Calm

15. Lakefront Cabin Near Solomons Island w/ Hot Tub

16. Just a getaway piece of property

17. Riverfront Home w/Dock · Fire Pit · Kids Play Area

18. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

19. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

20. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Find vacation rentals that suit your style

Top Callaway Hotel Reviews

Spark by Hilton California Lexington Park

avid hotel California - Lexington Park by IHG

Island Inn & Suites, an Ascend Collection Hotel

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

Quality Inn Solomons - Beacon Marina

Belle of the Chesapeake Bay

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Find out more about Callaway

Frequently asked questions

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