Callaway Vacation Rentals

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Our top choices for Callaway vacation rentals

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (46 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
The price is CA $197
CA $419 total
includes taxes & fees
May 27 - May 28
Soul Oasis - home on the Chesapeake Bay

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is CA $313
CA $467 total
includes taxes & fees
May 11 - May 12
Coles Point Marina

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.4 out of 10, Exceptional, (13 reviews)
"Pet friendly, easy check out, no cleaning involved."
United States
Naomi B.
The price is CA $279
CA $568 total
includes taxes & fees
Jun 2 - Jun 3
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Waterfront Reset—Kayaks, Games, Views & Total Calm

Waterfront Reset—Kayaks, Games, Views & Total Calm
Montross
10.0 out of 10, Exceptional, (31 reviews)
"Great spot"
United States
SHAWN W.
The price is CA $363
CA $769 total
includes taxes & fees
May 20 - May 21
Waterfront Reset—Kayaks, Games, Views & Total Calm

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

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is CA $277
CA $730 total
includes taxes & fees
May 17 - May 18
Anne & Fred`s Leonardtown Home W/ Arcade room!

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is CA $412
CA $495 total
includes taxes & fees
May 10 - May 11
Cottage Located on the Patuxent River!

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River
Lexington Park
10.0 out of 10, Exceptional, (8 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is CA $253
CA $541 total
includes taxes & fees
May 25 - May 26
Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

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

Riverfront Home w/Dock · Fire Pit · Kids Play Area
Montross
9.6 out of 10, Exceptional, (15 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is CA $246
CA $686 total
includes taxes & fees
May 12 - May 13
Riverfront Home w/Dock · Fire Pit · Kids Play Area

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
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.
The price is CA $369
CA $445 total
includes taxes & fees
May 12 - May 13
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (127 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
The price is CA $338
CA $725 total
includes taxes & fees
May 13 - May 14
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is CA $260
CA $601 total
includes taxes & fees
May 12 - May 13
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $752
CA $1,399 total
includes taxes & fees
May 25 - May 26
4-BR Waterfront Turret Home

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is CA $471
CA $580 total
includes taxes & fees
May 17 - May 18
2 Bedroom Cottage at Coles Point Marina

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is CA $339
CA $810 total
includes taxes & fees
May 11 - May 12
Come relax yourself a while

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully and tastefully decorated, immaculately clean, completely stocked top to bottom! You can tell by all of the details that these hosts care about curating a perfect stay for their guests. "
United States
Leslie K.
The price is CA $421
CA $807 total
includes taxes & fees
May 27 - May 28
Charming Waterfront 3-bedroom house in Piney Point

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"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.
The price is CA $369
CA $443 total
includes taxes & fees
May 11 - May 12
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

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

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is CA $662
CA $1,392 total
includes taxes & fees
May 12 - May 13
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is CA $583
CA $1,337 total
includes taxes & fees
May 12 - May 13
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Callaway. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS: This vacation home rental near Callaway is located on the waterfront and has a fireplace, a patio, and air-conditioning 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 can relax into your vacation with a garden and an arcade game room.

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 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.