Callaway Vacation Rentals from ￥39,729: Search Short-Term Rentals

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Our top choices for Callaway vacation rentals

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

1. 2 Acre Oasis with Private Beach! Family and dog friendly!

Leonardtown

Jonathan M.

￥125,146 total

includes taxes & fees

Oct 27 - Oct 28

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

2. Coles Point Marina

Hague

￥38,148 total

includes taxes & fees

Oct 5 - Oct 6

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

3. 4-BR Waterfront Turret Home

Solomons

Thomas S.

￥106,552 total

includes taxes & fees

Sep 28 - Sep 29

A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

4. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lusby

￥185,388 total

includes taxes & fees

Sep 28 - Sep 29

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.

￥86,166 total

includes taxes & fees

Sep 28 - Sep 29

6. 2 Bedroom Cottage at Coles Point Marina

Hague

￥62,804 total

includes taxes & fees

Sep 28 - Sep 29

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

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

Lexington Park

Andrea B.

￥56,357 total

includes taxes & fees

Oct 5 - Oct 6

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

8. Charming Waterfront 3-bedroom house in Piney Point

Piney Point

Meira

￥112,235 total

includes taxes & fees

Oct 19 - Oct 20

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Top Callaway Hotel Reviews

Sleep Inn & Suites California MD

10/10 Excellent

"Our accessible room was extremely clean and very useful for our needs."

The Inn at Leonardtown, an Ascend Collection Hotel

8/10 Good

"Welcoming staff, excellently situated in Downtown Leonardtown, decent offering of complimentary breakfast, including pre-made filled croissants. Only issue was my initial room suffered from external noise issues, suspected to be from the hotels air conditioning system (not the room), however the staff were more than happy to move me to another room which was much quieter."

House Right on the Potomac River - Great Sunrises & Sunsets

10/10 Excellent

"My multigenerational family of 9 adults & 2 kids were thoroughly happy in this rental. The outside was surrounded by gorgeous water views and the inside had a large kitchen to cook all the crabs & fish we caught! There are multiple nooks to get comfy in to unwind solo as well as large areas to gather all together. We’ve rented many vacation homes and this was the first that customized the entry combination to the last 4 digits of my cellphone. Nice touch for those renters wondering who else has access. We recommend wholeheartedly!!!"

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

10/10 Excellent

"Our week stay was so relaxing and fun. We enjoyed the sunrises and sunsets, views from the deck (it's my new 'happy place'!), the wildlife - ospreys, eagles, and the dolphins in the mornings. The games and things to do were also incredibly fun. The place was very clean, as well as beautifully decorated. Loved the towels too! I would highly recommend if you are looking for a relaxing non-hectic vacation on the water!Thank you, Monica, for providing us access to your home-away-from-home! 3"

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!"

Find out more about Callaway

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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?

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views: This vacation home rental near Callaway is located on a lake 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. Make the most of the selection of games in this rental home to help you unwind.

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

2. Coles Point Marina

3. 4-BR Waterfront Turret Home

4. Lakefront Cabin Near Solomons Island w/ Hot Tub

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

6. 2 Bedroom Cottage at Coles Point Marina

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

8. Charming Waterfront 3-bedroom house in Piney Point

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

10. Lakefront Cabin Near Solomons Island w/ Hot Tub

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

12. Soul Oasis - home on the Chesapeake Bay

13. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

14. Waterfront Game-Themed Getaway · Dock & Kayaks

15. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

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

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

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

19. Just a getaway piece of property

20. 'the Bayside Escape' Remote Chesapeake Bay Estate

Find vacation rentals that suit your style

Top Callaway Hotel Reviews

Sleep Inn & Suites California MD

Comfort Inn & Suites Lexington Park near Pax River

The Inn at Leonardtown, an Ascend Collection Hotel

Hilton Garden Inn Solomons

House Right on the Potomac River - Great Sunrises & Sunsets

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

Quality Inn Solomons - Beacon Marina

Belle of the Chesapeake Bay

Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD

Find out more about Callaway

Frequently asked questions

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