Holiday rentals in Callaway

Rolling Stone Farm - Charming 1930s House

Rolling Stone Farmhouse, a charming 1930’s home lovingly restored. Conveniently located within 5 miles of Patuxent River Naval Air Station, and 2 miles to St. Mary’s College of Maryland. Located on a farm with sweeping views of the fields and ponds, with an English garden right beside the back porch. Private, quiet, relaxing but within 10 minutes of shopping and restaurants. During your stay, the house and yard are dedicated to just you and your guests. Ask about the adjacent studio apartment.

Treetop Loft Retreat w/ Private Beach Access

Choose to stay in or adventure out: Experience our tucked-away loft 5 mins from beaches, 10 mins to Solomons & Calvert Cliffs. Totally private above-garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, living room & kitchen. Enjoy fast Wi-Fi, a 40" Smart TV, a cozy queen bed w/ heated mattress pad, and fireplace. NOTE: Smoke-free & peanut-free property as we are allergic to both. Scent Free in your space. Air Purifier. Melaluca cleaning products

Historic Rousby Hall, Waterfront, Pool, Beach

**Heated pool open to Nov 2. Thanksgiving chef dinner options** Rousby Hall is a stunning 5-star waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee additional).

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Serene setting great location surrounded by woods

The one-bedroom apartment will sleep 2 adults and 1 child under 18. In a serene setting with woods, a fish pond, and a comfortable patio. Separate code lock entrance. Well-equipped kitchen. Free WiFi, two TVs with Netflix and Amazon Prime. There is also a cedar sauna. Parking is on the property. Apartment situated near shops, restaurants, St. Mary's College and the Patuxent River Naval Air Station. 15 minutes from Chesapeake Bay, 1 hour to DC beltway. French and German also spoken.

Living on Island Time

Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

Stunning Sunsets on Breton Bay, Seaside apartment

Charming efficiency apartment decorated with a coastal theme overlooks Breton Bay. Use of pier for hanging out... or crabbing and fishing. Apartment is in the second floor of detached garage on the premises of a private home. Beautiful serene surroundings 5 min. from downtown Leonardtown with shopping, restaurants and events. Area offers historical sites, wonderful parks, a large Mennonite and Amish community, great restaurants and friendly people! 25 minutes from Solomons Island.

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum featuring live concerts by top name bands.