Shady Side holiday rentals

We found 620 holiday rentals — enter your dates for availability
Discover a selection of 12 homes and other holiday rentals in Shady Side that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you expect for your stay, which might include a garden and pool. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Shady Side

Showing deals for:25 Dec - 1 Jan

The Green Bedroom View
Terrace/patio
Great Room
Kitchen - Granite Island
Exceptional
(16 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
AU$14,525
for 7 nights, 1 home
AU$2,075 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Exterior Rear of House and Dock
Porch Dining Table
Upstairs Hall
Kitchen
Exceptional
(35 reviews)

Waterfront Home near Annapolis, MD

Harwood

8% off
AU$19,247
for 7 nights, 1 home
AU$2,750 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
Dining
Living area
Private kitchen
Exterior
Exceptional
(51 reviews)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville

8% off
AU$9,154
for 7 nights, 1 home
AU$1,308 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Dining
Private kitchen
Exterior
Living area
Excellent
(12 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
AU$5,174
for 7 nights, 1 home
AU$739 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
Private kitchen
Terrace/patio
Dining
Exterior
Exceptional
(31 reviews)

Charming 3BDR Bungalow Near Annapolis​

Riva

9% off
AU$3,273
for 7 nights, 1 home
AU$468 per night
includes taxes & fees
Charming 3BDR Bungalow Near Annapolis​
Dining
Living area
Interior
Exterior
Exceptional
(7 reviews)

Waterfront- 5-bedroom house with dock in charming North Beach

North Beach

8% off
AU$11,083
for 7 nights, 1 home
AU$1,583 per night
includes taxes & fees
Waterfront- 5-bedroom house with dock in charming North Beach
Beautiful views from your own private balcony!
Beautiful North Beach, MD
Open-concept living area and kitchen
Beautiful North Bach, MD
Exceptional
(21 reviews)

Unbelievable beach views for 6

North Beach

8% off
AU$3,824
for 7 nights, 1 apartment
AU$546 per night
includes taxes & fees
Unbelievable beach views for 6
Outdoor dining
Dining
Living area
Private kitchen
Exceptional
(34 reviews)

Sailor's Retreat! Perfect home for the getaway weekend. Best location!

Annapolis

8% off
AU$7,225
for 7 nights, 1 home
AU$1,032 per night
includes taxes & fees
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Living area
Living area
Interior
Living area
Exceptional
(11 reviews)

Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!

Riva

8% off
AU$5,906
for 7 nights, 1 home
AU$844 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Exterior
Pool
Living area
Interior
Exceptional
(233 reviews)

Stunning Waterfront Cottage in the Sailing Capital of the World!

Annapolis

8% off
AU$4,699
for 7 nights, 1 home
AU$671 per night
includes taxes & fees
Stunning Waterfront Cottage in the Sailing Capital of the World!
Property grounds
Foyer
Room
Exterior
Exceptional
(27 reviews)

Guest Quarters at the Inn - 102

North Beach

8% off
AU$2,091
for 7 nights, 1 apartment
AU$299 per night
includes taxes & fees
Guest Quarters at the Inn - 102
Living area
Exterior
Private kitchen
enjoy the rockers on the porch while sipping on a cup of coffee
Exceptional
(12 reviews)

Dog friendly! Next to Navy Stadium and DTA Shuttle!

Annapolis

8% off
AU$7,176
for 7 nights, 1 home
AU$1,025 per night
includes taxes & fees
Dog friendly! Next to Navy Stadium and DTA Shuttle!
Dining
Property grounds
Private kitchen
Water view from the kitchen
Exceptional
(36 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
AU$7,189
for 7 nights, 1 home
AU$1,027 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Rear Entry and Rooftop Balcony
Historic Annapolis and City Dock
Quaint Pinkney Street
Living Room with Cable Television
Exceptional
(147 reviews)

Historic Downtown Charmer, Water Views and Parking!

Annapolis

12% off
AU$4,264
for 7 nights, 1 home
AU$609 per night
includes taxes & fees
Historic Downtown Charmer, Water Views and Parking!
Room
Private kitchen
Interior
Dining
Exceptional
(7 reviews)

Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Annapolis

7% off
AU$8,269
for 7 nights, 1 home
AU$1,181 per night
includes taxes & fees
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Marina
Interior
Exterior
Interior
Exceptional
(55 reviews)

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

West River

12% off
AU$1,836
for 7 nights, 1 cottage
AU$262 per night
includes taxes & fees
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Dining
Terrace/patio
Private kitchen
Back yard and fire pit
Exceptional
(49 reviews)

Water Views - Close to Downtown Annapolis

Annapolis

5% off
AU$5,413
for 7 nights, 1 home
AU$773 per night
includes taxes & fees
Water Views - Close to Downtown Annapolis
This cozy dining room is a space that invites warmth and togetherness. It is designed to provide a delightful setting for shared meals and cherished moments with friends and family.
Property grounds
Complemented by earthy tones and natural materials such as wooden floors, this space provides a place to relax, watch TV or even host a game night.
The master bedroom boasts of natural light, en-suite bathroom and ample closet space.
Exceptional
(16 reviews)

Downtown Pinkney House w/Parking

Annapolis

7% off
AU$5,483
for 7 nights, 1 home
AU$783 per night
includes taxes & fees
Downtown Pinkney House w/Parking
Walking distance to gate 3
City Dock
Kitchen/lounging/dining room
Lounging room, Roku tv
Exceptional
(34 reviews)

Gem in Downtown Annapolis, close to USNA, St. John's College

Annapolis

8% off
AU$4,673
for 7 nights, 1 home
AU$668 per night
includes taxes & fees
Gem in Downtown Annapolis, close to USNA, St. John's College
Private, fenced outdoor space
Updated kitchen with all major appliances
Comfortable and cozy living room with fireplace (for aesthetic only), Smart TV, comfortable seating, games/puzzles, and books.
Dining room with space for 6
Exceptional
(9 reviews)

Timeless Charm Meets Modern Comfort

Annapolis

7% off
AU$4,143
for 7 nights, 1 home
AU$592 per night
includes taxes & fees
Timeless Charm Meets Modern Comfort
Exterior detail
1st floor kitchen
Room
Front of home. Apt door located under front stoop
Wonderful
(14 reviews)

18th Cent. Charm in Historic Downtown Annapolis

Annapolis

16% off
AU$2,774
for 7 nights, 1 apartment
AU$396 per night
includes taxes & fees
18th Cent. Charm in Historic Downtown Annapolis
Primary bedroom with king bed and cathedral ceiling
Bright and updated kitchen
Cozy family room with a queen sofa bed and room-darkening curtains
Bright and updated kitchen
Exceptional
(17 reviews)

Naval Academy Gate 1

Annapolis

7% off
AU$3,636
for 7 nights, 1 home
AU$519 per night
includes taxes & fees
Naval Academy Gate 1
Living area
Foyer
Living area
Exterior
Exceptional
(21 reviews)

Guest quarters at the inn - 205

North Beach

8% off
AU$2,525
for 7 nights, 1 apartment
AU$361 per night
includes taxes & fees
Guest quarters at the inn - 205
Bathroom
Foyer
Property grounds
Room
Exceptional
(19 reviews)

Guest Quarters at the Inn - 101

North Beach

8% off
AU$2,091
for 7 nights, 1 apartment
AU$299 per night
includes taxes & fees
Guest Quarters at the Inn - 101

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Shady Side getaway

Enjoy the museums and other features of Shady Side. Renowned for its shopping, restaurants and parks, this city welcomes all visitors. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Shady Side

Do you want to find top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Shady Side has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Thanksgiving Farm Wines (6.4 mi / 10.4 km)
  • Renditions Golf Club (9.7 mi / 15.6 km)
  • Chesapeake Beach Water Park (10.4 mi / 16.8 km)
  • Maryland Renaissance Festival (11.5 mi / 18.6 km)
  • St. Michaels Winery (16.2 mi / 26 km)
  • South River Golf Links (6.3 mi / 10.1 km)

Exploring the natural landscape of Shady Side

Whether you're an active traveller or just want to spend some time taking in the scenery, Shady Side is a great place to get out in nature. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Maryland Quiet Waters Park (7.1 mi / 11.4 km)
  • Bay Ridge Beach (7.9 mi / 12.7 km)
  • Northern Chesapeake Bay (12.4 mi / 19.9 km)
  • Sandy Point Beach (13.3 mi / 21.4 km)
  • Allen Pond Park (13.6 mi / 21.8 km)
  • Breezy Point Beach (15.3 mi / 24.6 km)

Transport options to and around Shady Side

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 21.6 mi (34.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into College Park, MD (CGS), which is 24.1 mi (38.7 km) away.

Frequently asked questions

What is the best area to stay in Shady Side when booking a holiday rental?
When considering a holiday rental in Shady Side, Maryland, the most appealing area to stay is the waterfront neighbourhood. This charming locale is known for its picturesque views of the Chesapeake Bay, making it a serene retreat for visitors. The area boasts a variety of properties, ranging from cosy cottages to more spacious homes, providing ample choices for different group sizes and preferences.One of the top attractions nearby is the stunning Broadneck Park, which offers lovely walking trails and picnic spots, superb for enjoying the natural beauty of the region. Additionally, the Shady Side area is in close proximity to the iconic Chesapeake Bay Maritime Museum, which showcases the rich maritime history of the region and features fascinating exhibits. Visitors can also indulge in local dining options that highlight fresh seafood, a true delight when staying in this area.
What is the most popular type of holiday rental accomodation in Shady Side?
In Shady Side, holiday houses are the most popular type of holiday rental, with about 27 available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking to enjoy a relaxing stay by the water. Additionally, several charming cottages can be found, offering a quaint and cosy atmosphere for those seeking a more intimate experience.
Are there any family house rentals in Shady Side?
In Shady Side, Maryland, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. This charming waterfront community offers a laid-back atmosphere with access to beautiful views of the Chesapeake Bay. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces superb for family gatherings or children to play in.Visitors can enjoy nearby attractions such as Sandy Point State Park, which offers beaches and picnic areas, ideal for a day out with the family. Additionally, the local area is known for its proximity to charming shops and restaurants, providing a taste of the area's culinary delights.
Are there pet-friendly house rentals in Shady Side?
In Shady Side, there are several pet-friendly house rentals available, making it a great choice for those travelling with furry companions. The area is known for its picturesque waterfront views and proximity to the Chesapeake Bay, providing a serene setting for a holiday. Many of the holiday homes come with amenities such as spacious backyards, outdoor seating areas, and fully equipped kitchens, ensuring a comfortable stay for both pets and their owners.Shady Side offers easy access to local parks and nature trails, great for daily walks and outdoor activities with pets. Nearby, you can explore scenic spots along the bay, where you and your pet can enjoy the fresh air and beautiful surroundings.
Are there any remote work holiday rentals in Shady Side?
In Shady Side, Maryland, there are several options for remote work holiday rentals, with approximately 27 properties available. Many of these accommodations cater specifically to those needing a productive work environment, featuring amenities such as high-speed internet, free Wi-Fi, and dedicated workspaces complete with desks and chairs. This makes it convenient for travellers who wish to balance work and leisure during their stay.The area itself offers a charming waterfront atmosphere, with easy access to local parks and scenic views of the Chesapeake Bay. Guests can enjoy nearby attractions, including marinas and nature trails, superb for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Shady Side?
In Shady Side, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals with ease. Many properties feature inviting decks or patios, superb for relaxing outdoors and enjoying the serene surroundings. Onsite parking is commonly available, ensuring convenience for those travelling by car. Additionally, rentals often provide coffee and tea makers, enhancing the comfort of a morning routine.
When is the best time to visit Shady Side for a holiday rental?
The peak season for holiday rentals in Shady Side, Maryland, is from May to July, with July being the most popular month for visitors. This vibrant period attracts families and outdoor enthusiasts looking to enjoy the beautiful Chesapeake Bay. You can partake in a variety of water activities such as kayaking, sailing, and fishing, all set against the picturesque backdrop of the bay.During the summer months, temperatures typically range from 20 to 30 degrees Celsius, providing ideal conditions for beach outings and outdoor barbecues. The lively option in Shady Side during this time makes it easy to meet fellow travellers and immerse yourself in the local culture.For those considering a more budget-friendly option, December is a lovely time to visit. Although it falls into the low season, the town offers a charming, quieter experience with the opportunity to enjoy winter strolls along the waterfront and the festive spirit of the holiday season.Ultimately, your choice of when to visit Shady Side will depend on whether you seek the bustling summer vibe or the tranquil charm of winter.
What are the top attractions in Shady Side?
In Shady Side, visitors can enjoy a variety of attractions that showcase the area's natural beauty and maritime charm. The local waterfront offers stunning views of the Chesapeake Bay, making it an ideal spot for leisurely walks or picnics. The nearby Sandy Point State Park is superb for outdoor activities such as hiking, birdwatching, and enjoying the beach, providing a great escape for families and nature enthusiasts alike.The community's maritime heritage can be explored through the Shady Side Historical Society, which hosts events and exhibits highlighting local history. Additionally, the area is known for its charming marinas, where visitors can enjoy boating, fishing, and kayaking.
Are all fees included in the Shady Side holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Shady Side holiday homes with parking?
Stayz offers a wide selection of holiday homes in Shady Side with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Shady Side holiday homes?
You can find great discounts on holiday homes in Shady Side on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Shady Side holiday home booking on Stayz?
To find Shady Side holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Shady Side?
A long-stay holiday home in Shady Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Shady Side holiday home?
Book your Shady Side holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Shady Side?
Prices for holiday homes in Shady Side vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Shady Side to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.