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Compare 151 Vacation Homes in Callaway with updated reviews, rates, and availability.

Coan River Cottage w/ Fire Pit, Pool, Movie Room
10.0 out of 10, Exceptional, (2)
"Jen was helpful and accommodating to our last minute requests."
Coan River Cottage w/ Fire Pit, Pool, Movie Room
Shewell's A-Frame on Mill Creek
10.0 out of 10, Exceptional, (1)
"Beautiful home overlooking the water. Excellent communication with the owners who answered all of my questions quickly. No complaints at all and im Looking forward to returning soon."
Shewell's A-Frame on Mill Creek
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, (102)
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
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Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, (4)
"We were in town for a friends wedding. This was the perfect location as it was right in between the Catholic Church for the nuptial mass and the reception site. This place certainly did not disappoint. There was plenty of space for our large family, the home was well equipped and stocked with the necessary items. It was a relatively short stay, but I wish we had a bit more time and better weather to enjoy the use of kayaks - our one free morning was a bit chilly for us Florida folks, and we had...
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
9.8 out of 10, Exceptional, (15)
"The house was incredible. My husband loved the master shower! The kids enjoyed the beach and swimming. Our youngest son (39) paddled the creek in the kayak. Our oldest son was able to dock his boat. The house had so many amenities. The kitchen was well stocked. There were games and books for all ages. We hope this home is available whenever we go back to visit family. Thank you, Victoria, for being so gracious!"
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
WATERFRONT!!! The River's Roost on The Patuxent River
10.0 out of 10, Exceptional, (11)
"Stayed here with a large family group that included grandparents and infants. The trip was a huge success. Peaceful, yet loaded with fun activities for the kids. Would highly recommend!"
WATERFRONT!!! The River's Roost on The Patuxent River
Shewell’s Rambler in the Chesapeake Ranch Estates
9.2 out of 10, Wonderful, (19)
"Nice and super clean. Nice location. We will stay again next time we visit family. "
Shewell’s Rambler in the Chesapeake Ranch Estates
Waterfront - renovated 3 bedrooms 2 full baths cottage
9.8 out of 10, Exceptional, (39)
"Wonderful view from the livingroom & the master bedroom. Clean house with hardwood floors. Great time for kids crabbing & a great place to fish -- one slot red, a few puppy drums, croakers, and even a couple of cownose rays that gave maybe the best fight I've had fishing! Michelle was very communicative & helpful. Thank you for a wonderful stay!"
Waterfront - renovated 3 bedrooms 2 full baths cottage
Blue Heron Retreat on the Water
10.0 out of 10, Exceptional, (4)
"Very pleased. Didn't get to use everything offered with my stay. Didn't matter. Definitely would recommend."
Blue Heron Retreat on the Water
Private Getaway at Four Waters Estate!
Private Getaway at Four Waters Estate!
Waterfront Relaxing Getaway
10.0 out of 10, Exceptional, (11)
"I was looking for a nice, quiet, and relaxing, vacation. This property did not disappoint. The house was comfortable, cozy, well stocked, and so clean. The view is incredible. Just sitting outside watching the river was so "Zen". I had one of the most restful vacations ever. I was there for a little over two weeks and I would have stayed longer if I could have, Kim, the host, was very friendly and helpful. I look forward to staying at this beautiful property again."
The price is AED 680
AED 1,545 total
includes taxes & fees
18 Jun - 19 Jun
Waterfront Relaxing Getaway
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (30)
"👍👍"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (171)
"Groomsmen stayed here for wedding. Great experience in a beautiful location. Swimming and kayaking right out the back door. Owners were very kind and helpful. Definitely recommend this beautiful spot."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
10.0 out of 10, Exceptional, (52)
"What a fantastic property! We loved staying here and our family had such a great time exploring. Sadly it was a drizzly, dreary weekend but we had one nice day to go down to the beach and the kids enjoyed playing in the water. We loved the variety of porches to sit on and have different views and there was plenty of room for the kids to play indoors when it was raining. Overall a great experience. Thank you!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
10.0 out of 10, Exceptional, (66)
"My family had a wonderful stay at Ivy Cove. We were in town for our niece’s wedding and it was close enough to participate in all family activities but far enough away to be a peaceful haven to relax. The house is beautiful. Beds were very comfortable. We really enjoyed the fire pit and game room. The owner was fantastic. We would absolutely stay again in this amazing home."
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
Waterfront house with private beach and pier
9.8 out of 10, Exceptional, (12)
"An amazing, secluded property that is perfect for a family or friends getaway. The rooms are clean, comfortable, and there were plenty of bathrooms. The property could improve by having additional toilet paper, shower toiletries, and towels, but the kitchen was very well stocked and there was plenty of seating. It really is a great house."
Waterfront house with private beach and pier
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
9.6 out of 10, Exceptional, (24)
"If you have a big group this is the place for you! We had a great time!!"
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Beach Club: your own private "Caribbean" resort
10.0 out of 10, Exceptional, (4)
"From the moment we booked until the moment we checked out, Beach Club far exceeded our expectations! The home itself had more than enough space for 14 people of varying ages, and the outbuildings provided a plethora of activities for diverse interests. The second-storey gazebo was a particular favorite, as was the 12-seat movie theater (with reclining and massage chairs!), and the very well-equipped clubhouse. Beach Club's amenities delivered in every category - design, comfort, and function....
Beach Club: your own private "Caribbean" resort
Beach Access Chesapeake Bay & Beach Retreat
9.6 out of 10, Exceptional, (14)
"This quaint beach house is just a short walk to a private beach. We really enjoyed our 3-night stay and took daily advantage of the location to the beach and other sites, such as farmer's markets. Great communication with Chris, the manager, leading up to the day we arrived."
Beach Access Chesapeake Bay & Beach Retreat
Cozy Catalina Cabin
10.0 out of 10, Exceptional, (10)
"Great stay in southern md. Would do again"
Cozy Catalina Cabin
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See all available properties in Callaway
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.

Other property types in Callaway

Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (54)
"We have stayed at this property twice and love it. Very peaceful, clean, and comfortable."
Waterfront Cottage in Beautiful Hoopers Island
Piney Point, private , Beach Front Cottage
10.0 out of 10, Exceptional, (76)
"We are so grateful to have had some time in this wonderful home. It was amazing to have the water at our back door. Every member of the family loved our stay here. Thank you so much!"
Piney Point, private , Beach Front Cottage
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (49)
"Beautiful little house right on the beach of the Chesapeake. Loved it. Everything was great and we will definitely be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
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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