Holiday houses in Callaway

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Popular amenities for Callaway holiday rentals

Other great holiday rentals in Callaway

Guest favourite
Home in Montross
4.93 out of 5 average rating, 202 reviews

The Glebe

Irma VRating, 5 stars2 weeks ago
We loved the open space concept in the house. It has beautiful views and a fire pit. Beds were clean and comfortable. Very well supplied kitchen. We will come back. Thanks,
Superhost
Home in Montross
4.88 out of 5 average rating, 232 reviews

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

SarahRating, 5 stars2 weeks ago
This cabin was everything we wanted and more! It’s in the perfect location, just a short drive to so many activities but also tucked away offering privacy. The house was so cozy it put us at ease as soon as we walked in. The owner was proactive and very quick to respond, including sending a great packing and local activity list a couple days in advance of our trip which came in very handy. Activities: This rental comes with guest passes to the private Shark Tooth Beach where our kids had so much fun finding real shark and manta ray teeth in the sand! Westmorland State Park and George Washington’s Birthplace both had great hiking and beaches for the kids. We visited Garners Produce twice where the kids fed animals and pedaled toy tractor’s while we picked up farm fresh milk and eggs. We spent our afternoons kayaking on the quiet lake soaking up the sunshine. We will definitely book another vacation at this cabin. You will not be disappointed with your stay at this little gem!
Superhost
Home in Lusby
4.89 out of 5 average rating, 37 reviews

Waterfront home with three bedrooms,3 full baths

JoyceRating, 5 stars3 weeks ago
Perfect weekend away! The home backed up to the Chesapeake Bay. The home was very relaxing. Would definitely stay again!
Guest favourite
Home in Colonial Beach
4.94 out of 5 average rating, 68 reviews

The Heaven at Colonial Beach

MelissaRating, 5 stars3 months ago
I’ve stayed at a lot of Airbnb’s and this was easily one of the best. Everything was exactly as described, and maybe even better than described. It had tons of amenities and a well stocked kitchen perfect for our large family. Spotless and beautiful. I highly recommend this home and would gladly stay there again.
Guest favourite
Home in Tilghman Island
4.97 out of 5 average rating, 30 reviews

Relax by the Water - Summer Dates Available!

RonnieRating, 5 stars3 months ago
Absolutely beautiful home! highly recommend!
Guest favourite
Home in Leonardtown
4.87 out of 5 average rating, 15 reviews

Garden Getaway

LindsayRating, 5 stars2 months ago
We had the pleasure of staying here during the winter while we looked for a place to live. It was perfect! Quiet and peaceful yet super close to all restaurants and stores. We had some snowfall and the views were stunning! Once it warmed up we even got to see some wild life in the woods behind us. Lovely huge porch! Lots of space in garden escape. Can bring the entire family and more!!! Nice big driveway for easy turned around. Patrick was beyond responsive for all my questions.Whether is was just informing be as something as simple as an Internet outage in the area or we had one situation with an unsure smell. Patrick acted immediately on the problem and it was resolved within 2 hours from start to finish. Cannot recommend this place enough!
Guest favourite
Cottage in Leonardtown
4.92 out of 5 average rating, 143 reviews

Breton Breeze

PailinRating, 5 stars2 weeks ago
If you’re looking for a peaceful place to restore your soul and allow you to reconnect with nature, you’ll love Jan’s cozy waterside cottage. Beautifully decorated and well equipped, you’ll find everything you need provided for your stay. Thanks to Jan for sharing this special place!
Guest favourite
Home in Scotland
5 out of 5 average rating, 29 reviews

Bay Front Beach House

NicholasRating, 5 stars2 weeks ago
Wow what a view. Family had a wonderful stay. House is big and well equipped. Internet is strong and plenty of hot water for all. House has access to a private beach that the small grandkids enjoyed. Definitely would stay again.

Destinations to explore

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  2. United States
  3. Maryland
  4. St. Mary's County
  5. Callaway