Entire home

Calloway Drive Retreat | House in Shady Side

Photo gallery for Calloway Drive Retreat | House in Shady Side

Living area
Outdoor dining
Exterior
Exterior
Living area

Reviews

9.4 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Washer
  • Kitchen
  • Dryer
  • Outdoor space
  • Parking available
  • Air conditioning

Explore the area

Map
Shady Side, MD
  • Shadyside Park
    ‪8 min drive‬
  • Annapolis City Dock
    ‪33 min drive‬
  • U.S. Naval Academy
    ‪34 min drive‬
  • Annapolis, MD (ANP-Lee)
    ‪23 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.

Property manager

Vacasa of Maryland
Premier Host

Languages

English, French, German, Italian, Spanish

Add dates for prices

Amenities

Kitchen
Washer
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
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Smoking is not permitted anywhere on the premises.
For information about quiet hours, please refer to the listing description.

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 Alumni Hall. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Shady Side, MD

What's nearby

  • Shadyside Park - 8 min drive - 4.7 km
  • Navy-Marine Corps Memorial Stadium - 31 min drive - 31.5 km
  • Annapolis City Dock - 33 min drive - 33.3 km
  • U.S. Naval Academy - 34 min drive - 33.7 km
  • Maryland Quiet Waters Park - 37 min drive - 34.3 km

Getting around

  • Fort Meade, MD (FME-Tipton) - 47 min drive

Restaurants

  • ‪Pirates Cove Restaurant - ‬15 min drive
  • ‪Skippers Pier - ‬14 min drive
  • ‪Happy Harbor Inn - ‬12 min drive
  • ‪Petie Greens - ‬13 min drive
  • ‪Old Stein Inn - ‬23 min drive

Frequently asked questions

Is Calloway Drive Retreat | House in Shady Side pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Calloway Drive Retreat | House in Shady Side?

Check-in begins at 4:00 PM.

What time is check-out at Calloway Drive Retreat | House in Shady Side?

Checkout is at 10:00 AM.

Where is Calloway Drive Retreat | House in Shady Side located?

Situated near the beach, this holiday home is 1.7 mi (2.7 km) from Franklin Point State Park and 2.9 mi (4.7 km) from Shadyside Park. Captain Avery Museum and Galesville Heritage Museum are also within 9 miles (15 km).

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 4 out of 6 reviews
Rating 8 - Good. 2 out of 6 reviews
Rating 6 - Okay. 0 out of 6 reviews
Rating 4 - Poor. 0 out of 6 reviews
Rating 2 - Terrible. 0 out of 6 reviews

10/10

Cleanliness

8.8/10

Check-in

8.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Jeffrey H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Military Bowl

Wonderful place
Stayed 2 nights in Dec 2024

10/10 Excellent

Regina E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Location

The place is cute and spacious enough for friend gathering. It is only 5mins away from the community beach and 25-30 from the bigger beaches. Perfect for a weekend getaway.
Stayed 2 nights in Jul 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Doug M.

The great quiet

It is just the perfect space to spend quality time with your family. The beach is in walking distance! So awesome!!
Stayed 3 nights in Apr 2024
This review comes from a trusted partner site and has not been verified.

8/10 Good

karen w.

Great place for a getaway

Closeness to my sons house. Room for those who participated. Wish we could stay longer. Life just speeds by
Stayed 3 nights in Aug 2024

8/10 Good

Lucy C.

Liked: Cleanliness, location, listing accuracy

Spacious in a cute neighborhood

We had lots of room to relax and hang out. The kitchen is very well appointed and we definitely could have cooked if we chose to. We enjoyed walking with nice views of the ocean. We especially enjoyed the osprey hanging out near their nest right off the pier.
Stayed 2 nights in Aug 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Rachel P.

Charming cottage in a beachy community

Loved the location of this cottage and the amenities that the rental and the neighborhood afford. We loved riding bikes around the neighborhood, to the beach and pier, and generally enjoying the proximity to the Bay. The home is well appointed with laundry, a fully equipped kitchen, and fast internet. Highly recommend this place, especially for families.

About the host

Hosted by Vacasa of Maryland

Host profile image

Languages:

English, French, German, Italian, Spanish

Premier Host

They consistently provide great experiences for their guests