Calloway Drive Retreat | House in Shady Side | House in Shady Side

9.0 (8 Reviews) |   3 Bedrooms  2 Bathrooms  6 Guests
Shady Side House | Calloway Drive Retreat | House in Shady Side

3 Bedroom 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.

Calloway Drive Retreat | House in Shady Side is located in Shady Side. Calloway Drive Retreat | House in Shady Side provides accommodation, featuring Sports/Activities, Bedding/Linens, Laundry, among other amenities. This House features Sports/Activities, Bedding/Linens, Laundry, to make your stay a comfortable one.

Calloway Drive Retreat | House in Shady Side has 3 Bedrooms , 2 Bathrooms, and max occupancy of 6 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Shady Side has interesting places to visit. If you want to learn more about the House in Shady Side, such as places to visit and things to do nearby, you can check below to learn more.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Amenities

Air Conditioner
Parking
TV
View
Ocean View
Balcony/Terrace
Oceanfront
Security/Safety
Sports/Activities
Bedding/Linens
Fireplace/Heating
Entertainment
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • 2 bathrooms
  • Towels provided
Bedroom
  • Bed sheets provided
  • 3 bedrooms
Kitchen
  • Cookware/dishes/utensils
  • Dishwasher
  • Coffee/tea maker
  • Microwave
  • Refrigerator
  • Stovetop
  • Oven
Laundry
  • Laundry facilities
  • Washing machine and dryer
Ocean view
  • Near the beach
Parking
  • Onsite parking
  • Electric car charging station on site
Pet Friendly
  • No pets allowed
Accessibility
  • Note from host: Smoking is not permitted anywhere on the premises.
  • Smoke-free property
Activities
  • Bicycle on site
  • Hiking nearby
  • Power boating nearby
  • Swimming nearby
  • Birdwatching nearby
  • Wildlife and game walks nearby
  • Fishing nearby
  • Water park
  • Hiking/biking trails nearby
Entertainment
  • Books
  • TV with cable/satellite service
  • Stereo
General
  • French
  • German
  • Italian
  • Spanish
  • English
Guest Services
  • Iron/ironing board
Internet
  • Internet access
Outdoors
  • Patio
Security/Safety
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Fire extinguisher
  • Smoke detector installed (host has indicated there is a smoke detector on the property)

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
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
Pets not allowed
Smoking Policy
Smoking is not permitted;smoking is not permitted anywhere on the premises.

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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

Reviews

Mila B.
Jul 28, 2025 07:00:00 AM
Review Score:   10
Summary: 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.
See All Reviews

FAQ's

Is this Shady Side house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Shady Side house have a swimming pool?

No, this Shady Side house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Shady Side house?

Best-rates for the Shady Side house starts from $222 per night with includes Air Conditioner, Balcony/Terrace, Fireplace/Heating, Internet, Kitchen, TV, Ocean View, Entertainment, View, Security/Safety, Sports/Activities, Bedding/Linens, Laundry, Parking, Oceanfront, Child Friendly with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is Shady Side house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Shady Side house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Shady Side house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Shady Side house?

Based on the information reported by the owner or manager, the Shady Side house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Shady Side house?

Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Check House Availability
Nightly rates from:
USD222
You will be redirected to  
Hot Deal - It has been viewed 153 times today
Not the right fit? Check out our other properties in Shady Side
Waterfront Home near Annapolis, MD From US $1,805
         

10.0 (33 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Grandma's Summer House Beverly Beach From US $178
         

|
10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Waterfront Home on the Chesapeake Bay! From US $623
         

10.0 (31 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Chesapeake Paradise LITE 4+br3ba Peaceful Watrfrnt From US $782
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Waterfront Sanctuary only 50 Min. From DC/Balt. From US $728
         

Sunset Cottage - West River Access and Views! From US $487
         

Sunrise Suite Exquisite Bay View Lux/Rom/Spiritual From US $241
         

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK From US $309
         

9.8 (83 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Lovely bay views with kayaks, bikes, fire pit, crabbing & more From US $426
         

Beach Cottage | Walk to Beverly Triton Park From US $338
         

9.8 (7 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt From US $654
         

9.4 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Adorable waterside cottage with pool Beach community From US $456
         

9.2 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Steps to Chesapeake Bay! 'Callaway Drive Retreat' From US $223
         

9.0 (6 Reviews)
House
  • TV
  • Balcony/Terrace
  • Security/Safety
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis From US $201
         

Franklin At The Bay From US $433
         

New
House
  • Air Conditioner
  • Parking
  • TV
Enchanting West River Retreat From US $527
         

10.0 (9 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Zen Sunset Retreat on Waterfront at West River, MD From US $712
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • TV