Entire home

Calloway Drive Retreat | House in Shady Side

Vacation home in Shady Side with kitchen and patio

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Outdoor dining - Calloway Drive Retreat | House in Shady Side (Shady Side)
Fridge, microwave, oven, stovetop - Calloway Drive Retreat | House in Shady Side (Shady Side)
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Interior - Calloway Drive Retreat | House in Shady Side (Shady Side)
Fridge, microwave, oven, stovetop - Calloway Drive Retreat | House in Shady Side (Shady Side)
Escape to Calloway Drive Retreat, a lovely home near the bay where you can create lasting memories. Relax in the cool air of partial air-conditioning while streaming your favorite shows or take advantage of modern amenities like a private washer/dryer and bikes for neighborhood rides.

Reviews

9.0 out of 10
Wonderful

Entire home

3 bedrooms2 bathroomsSleeps 6

Popular amenities

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

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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 amenities

Beach

  • Beach nearby

Internet

  • Available in the house: Internet access

Parking and transportation

  • Electric car charging station on site
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Towels provided

Entertainment

  • Books
  • Stereo
  • TV with cable/satellite channels

Outdoor areas

  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed
  • Note from host: Smoking is not permitted anywhere on the premises.

Services and conveniences

  • Iron/ironing board

Things to do

  • Bicycles
  • Water park
  • Birdwatching nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Motor boating nearby
  • Swimming nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Bicycles
  • Electric car charging station

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

For information about quiet hours, please refer to the listing description.

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

107414

About the neighborhood

Map
Shady Side, MD

What's nearby

  • Franklin Point State Park - 5 min drive - 3.1 km
  • Shadyside Park - 6 min drive - 4.5 km
  • Captain Avery Museum - 7 min drive - 4.8 km
  • Galesville Heritage Museum - 14 min drive - 15.1 km
  • U.S. Naval Academy - 34 min drive - 41.1 km

Getting around

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

Restaurants

  • ‪Dunkin' - ‬19 min drive
  • ‪Boat House - ‬12 min drive
  • ‪Skippers Pier Restaurant and Dock Bar - ‬14 min drive
  • ‪7-Eleven - ‬10 min drive
  • ‪Wharf 38 - ‬13 min drive

Frequently asked questions

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

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the 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?

Check-out is at 10:00 AM.

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

Situated near the beach, this vacation home is steps from Chesapeake Bay and Northern Chesapeake Bay. Franklin Point State Park and Shadyside Park are also within 3 mi (5 km).

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Reviews

Calloway Drive Retreat | House in Shady Side Reviews

9.0

Wonderful

10

Cleanliness

10

Location
Rating 10 - Excellent. 5 out of 8 reviews
Rating 8 - Good. 2 out of 8 reviews
Rating 6 - Okay. 1 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

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.

10/10 Excellent

Mila B.

Very clean home with lots of amenities!

This was a lovely and very clean home. It also included several amenities such as bikes, a gazebo with picknick tables and aa mosquito mesh, and a grill. We had a great time exploring the area and walking to 'Sandy Beach', as well as visiting the nearby restaurants and farmers markets.
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.

6/10 Okay

Tom P.

Liked: Check-in, location, listing accuracy
Stayed 6 nights in Jun 2025