Callaway Vacation Rentals

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Our top choices for Callaway vacation rentals

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, (10 reviews)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
The price is CA $176
CA $436 total
includes taxes & fees
Feb 9 - Feb 10
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (41 reviews)
"The cozy cabin had everything needed for a comfortable stay. It was in a very private setting with the beach access a few houses away. You can hear the Chesapeake bay lapping at the shore and catch a glimpse of sail boats going by. We enjoyed our time at the home."
United States
Mary G.
The price is CA $187
CA $407 total
includes taxes & fees
Feb 10 - Feb 11
Soul Oasis - home on the Chesapeake Bay

Waterfront Retreat | Sunset Views + Outdoor Lounge

Waterfront Retreat | Sunset Views + Outdoor Lounge
Leonardtown
The price is CA $150
CA $485 total
includes taxes & fees
Feb 8 - Feb 9
Waterfront Retreat | Sunset Views + Outdoor Lounge

Luxury Modern Waterfront Retreat

Luxury Modern Waterfront Retreat
Montross
9.6 out of 10, Exceptional, (14 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is CA $193
CA $620 total
includes taxes & fees
Feb 10 - Feb 11
Luxury Modern Waterfront Retreat

Back Creek Villa Open Deck Solomons Island Maryland

Back Creek Villa Open Deck Solomons Island Maryland
Solomons
Back Creek Villa Open Deck Solomons Island Maryland

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is CA $364
CA $512 total
includes taxes & fees
Feb 8 - Feb 9
Coles Point Marina

Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Lexington Park
10.0 out of 10, Exceptional, (5 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is CA $219
CA $501 total
includes taxes & fees
Feb 9 - Feb 10
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

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 $283
CA $718 total
includes taxes & fees
Feb 8 - Feb 9
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Easthaven: Game-Theme Waterfront Retreat+Bring Pup

Easthaven: Game-Theme Waterfront Retreat+Bring Pup
Montross
10.0 out of 10, Exceptional, (30 reviews)
"Great spot"
United States
SHAWN W.
The price is CA $267
CA $645 total
includes taxes & fees
Mar 1 - Mar 2
Easthaven: Game-Theme Waterfront Retreat+Bring Pup

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (1 review)
"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.
The price is CA $410
CA $791 total
includes taxes & fees
Feb 8 - Feb 9
Charming Waterfront 3-bedroom house in Piney Point

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 $479
CA $1,035 total
includes taxes & fees
Feb 8 - Feb 9
4-BR Waterfront Turret Home

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (42 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is CA $363
CA $438 total
includes taxes & fees
Feb 8 - Feb 9
Cottage Located on the Patuxent River!

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 $451
CA $1,212 total
includes taxes & fees
Feb 10 - Feb 11
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

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
Feb 8 - Feb 9
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is CA $328
CA $406 total
includes taxes & fees
Feb 8 - Feb 9
2 Bedroom Cottage at Coles Point Marina

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 $444 total
includes taxes & fees
Feb 12 - Feb 13
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is CA $338
CA $810 total
includes taxes & fees
Feb 12 - Feb 13
Come relax yourself a while
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?

Beach & River Retreat. Spectacular house with private sand beach and hot tub!: This vacation home rental near Callaway is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

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.