Entire home
Calloway Drive Retreat | House in Shady Side
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Reviews
9.0 out of 10
Wonderful
3 bedrooms 2 bathrooms Sleeps 6
Popular amenities
Explore the area

Shady Side, MD
- Shadyside Park8 min drive
- Annapolis City Dock41 min drive
- U.S. Naval Academy42 min drive
- Washington, DC (DCA-Ronald Reagan Washington National)63 min drive
Rooms & beds
3 bedrooms (sleeps 6)
Bedroom 1
1 Queen Bed
Bedroom 2
1 Queen Bed
Bedroom 3
2 Single Beds
2 bathrooms
Bathroom 1
Bathroom 2
Spaces
Deck or patio
Kitchen
About this property
Calloway Drive Retreat | House in Shady Side
Calloway Drive Retreat
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
Steps from the bay, curate all of your favorite vacation memories at the Calloway Drive Retreat! Spacious, tastefully decorated, and ready to host - this lovely home boasts comfortable furnishings and modern amenities. Hang out inside amongst the cool air of the partial air-conditioning while cooking, streaming your favorite shows, and refreshing your vacation garb in the private washer/dryer.
Outside, enjoy dining alfresco on the covered patio, visiting with your loved ones under the radiant sunshine, or taking the provided bikes for a ride through the neighborhood. Less than 20 miles from your stay, discover the Franklin Point Park Beach, Captain Avery Museum, Beverly Triton Nature Park, Renditions Golf Course, Chesapeake Beach Water Park, and Historic Annapolis.
House Rules
There is free parking for 3 car(s).
Check in time: 4:00 PM
Check out time: 10:00 AM
All guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10 p.m. to 8 a.m.
No smoking is permitted anywhere on the premises.
This Vacasa Guestworks vacation rental is operated and managed locally by an independent host.
Prior to your arrival, you will receive local host contact information, who will manage your guest reservation. Your local host will provide in-stay support, secure entry, and arrange pre- and post-stay housekeeping services.
If you need anything during your stay, the home’s independent local host is ready to help 24/7! Guestworks is a service offering of Vacasa that allows homeowners to smoothly and efficiently manage their own properties.
Parking notes: There is free parking available for 3 vehicles.
Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.
Due to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
Steps from the bay, curate all of your favorite vacation memories at the Calloway Drive Retreat! Spacious, tastefully decorated, and ready to host - this lovely home boasts comfortable furnishings and modern amenities. Hang out inside amongst the cool air of the partial air-conditioning while cooking, streaming your favorite shows, and refreshing your vacation garb in the private washer/dryer.
Outside, enjoy dining alfresco on the covered patio, visiting with your loved ones under the radiant sunshine, or taking the provided bikes for a ride through the neighborhood. Less than 20 miles from your stay, discover the Franklin Point Park Beach, Captain Avery Museum, Beverly Triton Nature Park, Renditions Golf Course, Chesapeake Beach Water Park, and Historic Annapolis.
House Rules
There is free parking for 3 car(s).
Check in time: 4:00 PM
Check out time: 10:00 AM
All guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10 p.m. to 8 a.m.
No smoking is permitted anywhere on the premises.
This Vacasa Guestworks vacation rental is operated and managed locally by an independent host.
Prior to your arrival, you will receive local host contact information, who will manage your guest reservation. Your local host will provide in-stay support, secure entry, and arrange pre- and post-stay housekeeping services.
If you need anything during your stay, the home’s independent local host is ready to help 24/7! Guestworks is a service offering of Vacasa that allows homeowners to smoothly and efficiently manage their own properties.
Parking notes: There is free parking available for 3 vehicles.
Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.
Due to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
Parking available
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House Rules
Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Smoking is not permitted anywhere on the premises.
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
About the area
Shady Side
Located in Shady Side, this holiday home is near the beach. Captain Avery Museum and Galesville Heritage Museum are cultural highlights, and some of the area's activities can be experienced at Thanksgiving Farm Wines and South River Golf Links. Looking to enjoy an event or a game while in town? See what's happening at Navy-Marine Corps Memorial Stadium or Tose Family Tennis Center. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Shady Side, MD
What's nearby
- Shadyside Park - 8 min drive - 4.5 km
- Navy-Marine Corps Memorial Stadium - 39 min drive - 40.8 km
- Annapolis City Dock - 41 min drive - 42.2 km
- U.S. Naval Academy - 42 min drive - 42.5 km
- Maryland Quiet Waters Park - 53 min drive - 43.9 km
Getting around
Restaurants
- Dunkin' - 19 min drive
- Pirates Cove Restaurant
- Happy Harbor Restaurant - 12 min drive
- Skippers Pier Restaurant and Dock Bar - 14 min drive
- Stan and Joes Riverside - 15 min drive
Frequently asked questions
About the host
Hosted by Vacasa of Maryland

Languages:
English, French, German, Italian, Spanish
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