Callaway Vacation Rentals from $268: Search Short-Term Rentals

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Our top choices for Callaway vacation rentals

1. Soul Oasis - home on the Chesapeake Bay

Lusby

Melinda S.

$286 nightly

Sep 3 - Sep 4

Total with taxes and fees

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

Lexington Park

Andrea B.

$379 nightly

Sep 8 - Sep 9

Total with taxes and fees

3. Cozy Virginia Potomac Riverfront Cottage

Hague

Ashley D.

$315 nightly

Aug 16 - Aug 17

Total with taxes and fees

4. Coles Point Marina

Hague

$295 nightly

Sep 3 - Sep 4

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

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

Leonardtown

Christy C.

$539 nightly

Aug 9 - Aug 10

Total with taxes and fees

6. Charming Waterfront 3-bedroom house in Piney Point

Piney Point

Meira

$723 nightly

Aug 10 - Aug 11

Total with taxes and fees

7. Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Hague

"We were going to an evening event at Stratford Hall (about 25 min away). There is so much history in the area. Beautiful spot on the river. The screened in porch was the bomb! Huge. So relaxing. Well stocked. Easy check out. Do pay attention to room configuration. The bedroom with twins was a loft like area but had the nicer bathroom. We used the kayaks. Had everything we needed. Host communication was great despite Vrbo platform was a challenge."

Paige

$530 nightly

Aug 9 - Aug 10

Total with taxes and fees

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

Point Lookout

William L.

$336 nightly

Aug 17 - Aug 18

Total with taxes and fees

9. 4-BR Waterfront Turret Home

Solomons

Thomas S.

$633 nightly

Sep 8 - Sep 9

Total with taxes and fees

10. 2 Bedroom Cottage at Coles Point Marina

Hague

$389 nightly

Aug 9 - Aug 10

Total with taxes and fees

11. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

$253 nightly

Sep 1 - Sep 2

Total with taxes and fees

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

Lusby

Sarah R.

$995 nightly

Aug 12 - Aug 13

Total with taxes and fees

13. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lusby

Tanya S.

$1,055 nightly

Aug 10 - Aug 11

Total with taxes and fees

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

Montross

Evelyn C.

$541 nightly

Sep 2 - Sep 3

Total with taxes and fees

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

Montross

N C.

$522 nightly

Sep 1 - Sep 2

Total with taxes and fees

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

Lusby

Tova A.

$753 nightly

Aug 16 - Aug 17

Total with taxes and fees

17. Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

Mollie O.

18. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lusby

$1,031 nightly

Aug 10 - Aug 11

Total with taxes and fees

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

Fishing Creek

Thomas S.

$308 nightly

Aug 9 - Aug 10

Total with taxes and fees

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

Fishing Creek

Robin E.

$308 nightly

Aug 9 - Aug 10

Total with taxes and fees

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Top Callaway Hotel Reviews

Comfort Inn & Suites Lexington Park near Pax River

10/10 Excellent

"Clean, good location, good breakfast, attentive staff"

Super 8 by Wyndham Lexington Park/California Area

8/10 Good

"I like the idea shop's were near by you can walk to family friendly clean room staff friendly need to stairup breakfast didn't have any thing to eat it was just coffee and some Walmart honey buns out of a box that not continental breakfast overall if you looking for a overnight stay it's good for that."

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 $268 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?

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly: This vacation home rental near Callaway is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. 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 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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Upfront pricing

Check prices for these dates

Our top choices for Callaway vacation rentals

1. Soul Oasis - home on the Chesapeake Bay

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

3. Cozy Virginia Potomac Riverfront Cottage

4. Coles Point Marina

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

6. Charming Waterfront 3-bedroom house in Piney Point

7. Rustic 3BR Waterfront Cabin with Firepit + Dock Access

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

9. 4-BR Waterfront Turret Home

10. 2 Bedroom Cottage at Coles Point Marina

11. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

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

13. Lakefront Cabin Near Solomons Island w/ Hot Tub

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

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

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

17. Beach House w/TheaterRm, GameRm, Outdoor Shwr

18. Lakefront Cabin Near Solomons Island w/ Hot Tub

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

Comfort Inn & Suites Lexington Park near Pax River

Super 8 by Wyndham Lexington Park/California Area

Hilton Garden Inn Solomons

Quality Inn Solomons - Beacon Marina

The Inn at Leonardtown, an Ascend Collection Hotel

Hampton Inn by Hilton Lexington Park

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

Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Find out more about Callaway

Frequently asked questions

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