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Steps to Chesapeake Bay! 'Callaway Drive Retreat'

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TV, stereo - Steps to Chesapeake Bay! 'Callaway Drive Retreat' (Shady Side)
Exterior - Steps to Chesapeake Bay! 'Callaway Drive Retreat' (Shady Side)
3 bedrooms, iron/ironing board, Internet, bed sheets - Steps to Chesapeake Bay! 'Callaway Drive Retreat' (Shady Side)
Fridge, microwave, stovetop, dishwasher - Steps to Chesapeake Bay! 'Callaway Drive Retreat' (Shady Side)
Interior - Steps to Chesapeake Bay! 'Callaway Drive Retreat' (Shady Side)
Steps to Chesapeake Bay! 'Callaway Drive Retreat' provides a playground and more.

Reviews

9.2 out of 10
Wonderful

Entire home

3 bedrooms2 bathrooms

Popular amenities

  • Kitchen
  • Washing machine
  • Outdoor space

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.

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

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.

-- THE PROPERTY --

STR00743

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

-- THE LOCATION --

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.

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- There is free parking for 3 cars
- Quiet hours are from 10:00 PM to 8:00 AM

Property amenities

Internet

  • Available in the house: Internet access

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Stereo
  • TV with cable/satellite channels

Outdoor areas

  • Patio

Laundry

  • Washing machine

Comfort

  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Things to do

  • Bicycles
  • Hiking/biking trails nearby
  • Motor boating 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

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Policies

Check-in

Check-in time starts at 4:00 PM

Minimum check-in age - 18

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

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

About the area

Shady Side is home to this holiday home. Thanksgiving Farm Wines and South River Golf Links are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. 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. Discover the area's water adventures with nearby power boating, or enjoy the great outdoors with hiking/biking trails. Visit our Shady Side travel guide
View more Holiday homes in Shady Side
Map
Shady Side, MD

What's nearby

  • Franklin Point State Park
    4 min drive - 3.1 km
  • Shadyside Park
    6 min drive - 5.2 km
  • Captain Avery Museum
    8 min drive - 5.9 km
  • Galesville Heritage Museum
    14 min drive - 15.1 km
  • Smithsonian Environmental Research Center
    18 min drive - 19.8 km

Getting around

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

Restaurants

  • Bayside Bull
    19 min drive
  • 7-Eleven
    10 min drive
  • Dunkin'
    19 min drive
  • Jesse Jay’s
    8 min drive
  • Happy Harbor Restaurant
    12 min drive

Frequently asked questions

Is Steps to Chesapeake Bay! 'Callaway Drive Retreat' pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Steps to Chesapeake Bay! 'Callaway Drive Retreat'?

Check-in begins at 4:00 PM.

What time is check-out at Steps to Chesapeake Bay! 'Callaway Drive Retreat'?

Checkout is at 10:00 AM.

Where is Steps to Chesapeake Bay! 'Callaway Drive Retreat' located?

Situated in Shady Side, this holiday home is steps away from Chesapeake Bay and Northern Chesapeake Bay. Franklin Point State Park and Shadyside Park are also within 3 miles (5 km).

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Steps to Chesapeake Bay! 'Callaway Drive Retreat' Reviews

Reviews

Wonderful

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 5 out of 7 reviews
Rating 8 - Good. 1 out of 7 reviews
Rating 6 - Okay. 1 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

10

Cleanliness

10

Location

Reviews

Verified

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
Verified

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
Verified

10/10 Excellent

Jeff H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful place to stay. The water is an added bonus!
Stayed 2 nights in Dec 2025
Verified

10/10 Excellent

Jeffrey H.

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

Military Bowl

Wonderful place
Stayed 2 nights in Dec 2024
Verified

10/10 Excellent

Shawn T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Nov 2025
Verified

6/10 Okay

Tom P.

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