Shady Side holiday rentals

We found 618 holiday rentals — enter your dates for availability
Discover a selection of 13 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:13 Nov - 20 Nov

Kitchen
Porch Dining Table
Swimming Pool
Exterior Rear of House and Dock
Exceptional
(33 reviews)

Waterfront Home near Annapolis, MD

Harwood

8% off
AU$18,934
for 7 nights, 1 home
AU$2,705 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
Exterior
Terrace/patio
The Green Bedroom View
Kitchen - Granite Island
Exceptional
(15 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
AU$14,298
for 7 nights, 1 home
AU$2,043 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Large, beautifully updated kitchen area is perfect for meal times.
Marina
Additional dining area off of the living room
The kitchen opens up to a spacious sitting room complete with large flat screen tv and fireplace.
Exceptional
(37 reviews)

West Annapolis Cottage- 6BR Walk to Navy Stadium

Annapolis

7% off
AU$9,008
for 7 nights, 1 home
AU$1,287 per night
includes taxes & fees
West Annapolis Cottage- 6BR Walk to Navy Stadium
Dining
Private kitchen
Interior
Room
Exceptional
(20 reviews)

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis

16% off
AU$8,167
for 7 nights, 1 home
AU$1,167 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
Living area
Property grounds
Private kitchen
Beach
Exceptional
(91 reviews)

Chesapeake Bay Cottage

Deale

8% off
AU$3,467
for 7 nights, 1 cottage
AU$495 per night
includes taxes & fees
Chesapeake Bay Cottage
Exterior
Terrace/patio
Living area
Private kitchen
Exceptional
(31 reviews)

Charming 3BDR Bungalow Near Annapolis​

Riva

9% off
AU$3,195
for 7 nights, 1 home
AU$456 per night
includes taxes & fees
Charming 3BDR Bungalow Near Annapolis​
Living area
Exterior
Exterior
Private kitchen
Exceptional
(5 reviews)

Waterfront Sanctuary only 50 Min. From DC/Balt.

Shady Side

12% off
AU$7,852
for 7 nights, 1 home
AU$1,122 per night
includes taxes & fees
Waterfront Sanctuary only 50 Min. From DC/Balt.
Living area
Private kitchen
Dining
Dining
Excellent
(8 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
AU$5,054
for 7 nights, 1 home
AU$722 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
Living area
Pool
Interior
Marina
Exceptional
(229 reviews)

Stunning Waterfront Cottage in the Sailing Capital of the World!

Annapolis

8% off
AU$4,590
for 7 nights, 1 home
AU$656 per night
includes taxes & fees
Stunning Waterfront Cottage in the Sailing Capital of the World!
Breakfast room
Back deck
2nd floor full bedroom
Kitchen
Exceptional
(76 reviews)

Charming Annapolis Victorian

Annapolis

8% off
AU$8,583
for 7 nights, 1 home
AU$1,226 per night
includes taxes & fees
Charming Annapolis Victorian
Dining
Private kitchen
Interior
Exterior detail
Exceptional
(11 reviews)

Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access

Riva

21% off
AU$4,040
for 7 nights, 1 home
AU$577 per night
includes taxes & fees
Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access
Living area
Living area
Dining
Living area
Exceptional
(9 reviews)

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

Riva

8% off
AU$5,769
for 7 nights, 1 home
AU$824 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Bathroom
Foyer
Exterior
Room
Exceptional
(26 reviews)

Guest Quarters at the Inn - 102

North Beach

8% off
AU$2,083
for 7 nights, 1 apartment
AU$298 per night
includes taxes & fees
Guest Quarters at the Inn - 102
Bright stairway to second floor where 3 bedrooms and 2 full baths await
Open floor plan
Exterior
Primary bedroom has king bed
Exceptional
(58 reviews)

Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience

Annapolis

6% off
AU$7,081
for 7 nights, 1 home
AU$1,012 per night
includes taxes & fees
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
Beautiful views from your own private balcony!
Beautiful North Beach, MD
Open-concept living area and kitchen
Beautiful North Bach, MD
Exceptional
(18 reviews)

Unbelievable beach views for 6

North Beach

8% off
AU$2,775
for 7 nights, 1 apartment
AU$396 per night
includes taxes & fees
Unbelievable beach views for 6
Exterior
Dining
Outdoor dining
Living area
Exceptional
(34 reviews)

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

Annapolis

8% off
AU$6,696
for 7 nights, 1 home
AU$957 per night
includes taxes & fees
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Comfortable family room with reclining sofa, Smart TV and remote controlled window shades.
Light and bright dining room with space for 6 (plus a high chair).
Light and bright dining room with space for 6 (plus a high chair).
Recently renovated kitchen with quartz countertops, stainless steel appliances, and all the gadgets, tools, and amenities you need to cook wonderful meals.
Exceptional
(7 reviews)

Cozy Cottage with Beach Access

Annapolis

7% off
AU$3,515
for 7 nights, 1 home
AU$502 per night
includes taxes & fees
Cozy Cottage with Beach Access
Adirondack Chairs to Enjoy the Wooded Preserve
Exterior
Fully Loaded Kitchen with Island Seating
Main Living Area
Exceptional
(13 reviews)

Uptown Annapolis - Peaceful, Sparkling, 1 Bed/1 Bath Apartment, Sleeps 3-4

Annapolis

12% off
AU$2,690
for 7 nights, 1 home
AU$384 per night
includes taxes & fees
Uptown Annapolis - Peaceful, Sparkling, 1 Bed/1 Bath Apartment, Sleeps 3-4
Quaint Pinkney Street
Historic Annapolis and City Dock
Living Room with Cable Television
Ship's Ladder Stairs to Rooftop Deck
Exceptional
(144 reviews)

Historic Downtown Charmer, Water Views and Parking!

Annapolis

12% off
AU$4,165
for 7 nights, 1 home
AU$595 per night
includes taxes & fees
Historic Downtown Charmer, Water Views and Parking!
Dining
Private kitchen
Room
Exterior
Exceptional
(7 reviews)

Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Annapolis

7% off
AU$7,021
for 7 nights, 1 home
AU$1,003 per night
includes taxes & fees
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Park with ease in the permeable gravel driveway and enjoy sustainable living with rooftop solar panels and lush native landscaping.
The upstairs primary suite includes a queen bed and private bath with a deep soaking tub—your own peaceful hideaway.
Dining
Whether curling up with a book or logging into a Zoom call, this light-filled space is both calm and versatile.
Exceptional
(6 reviews)

Unique and central in Eastport

Annapolis

7% off
AU$4,126
for 7 nights, 1 home
AU$589 per night
includes taxes & fees
Unique and central in Eastport
Kitchen Island
String lights on the patio make it the perfect place to unwind in the evening!
Dining room table
Welcome!
Exceptional
(20 reviews)

***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.

Annapolis

8% off
AU$7,562
for 7 nights, 1 home
AU$1,080 per night
includes taxes & fees
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
Interior
Interior
Exterior
Interior
Exceptional
(53 reviews)

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

West River

12% off
AU$1,790
for 7 nights, 1 cottage
AU$256 per night
includes taxes & fees
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Water view from the kitchen
Property grounds
Interior
Dining
Exceptional
(29 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
AU$6,905
for 7 nights, 1 home
AU$986 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
  • 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)
  • 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)
  • Renditions Golf Club (9.7 mi / 15.6 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)
  • Breezy Point Beach (15.3 mi / 24.6 km)
  • Patuxent River (25.4 mi / 40.8 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 most popular type of holiday home accommodation in Shady Side?
Houses are the most popular style of holiday home in Shady Side, according to our data. Even if you have a different vision in mind, Stayz has properties in many sizes and shapes. Browse our many options to find your perfect Shady Side pad.
How much does it cost to rent a holiday home in Shady Side?
The average price for a holiday home in Shady Side can vary based on factors such as property type, season and length of stay. Whether you're searching for a sprawling villa with a pool or a cosy cottage for just you and your sweetheart, just add your dates of travel to see stays with unbeatable value.
How much does it cost to rent a beach house in Shady Side?
Prices for beach houses in Shady Side may vary depending on the size and type of the property and time of year you're travelling. All you have to do is enter your travel dates into Stayz and how many guests to see your options and prices. From there you can use the filters to tailor your search by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday homes in Shady Side?
You're in luck! There are. You can pick from seven holiday homes that allow pets in Shady Side. Several of our pet-friendly holiday homes even come with a backyard for your furry pal to play around in, dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find a pad that'll get tails wagging on Stayz.
What are popular home amenities in Shady Side?
A fireplace, a firepit and a garden are the most popular home amenities in Shady Side. Whether you're heading away by yourself, with your spouse or a group of family members, Stayz can help you find a holiday home that suits your style with a load of extras you'll love.
Are there large group holiday homes in Shady Side?
Take your pick of six Stayz holiday homes in Shady Side that can accommodate a group of five or more people. You'll enjoy all the privacy and space you need to spend time with the people you're holidaying with — and no one else.
Are there holiday homes in Shady Side that welcome kids?
With seven family-friendly holiday homes available in Shady Side, there's never been a better time to introduce your children to the joys of travel. Simply click on our "Properties good for families" filter to view stays that feature amenities perfect for holidaying families, like dining rooms, private pools, hot tubs and entertainment areas.
What are the top attractions for families in Shady Side?
Keeping the kids occupied during your Shady Side holiday is a snap with these leading family-friendly attractions:
  • Annapolis Maritime Museum
  • Triton Beach
  • Annapolis Sailing School
Are there holiday homes with WiFi in Shady Side?
Whether you want to keep up with the headlines, look over emails or surf social media, there are six holiday homes with WiFi in Shady Side. Check the "WiFi" box when searching on Stayz and stay connected on your getaway.
How can I find holiday homes with air conditioning in Shady Side?
You'll find seven holiday homes with air conditioning in Shady Side giving you that cool, cool breeze and extra comfort level. Enter your preferred dates of travel and then use our filter tool to find properties with air conditioning.
How old do you have to be to rent a holiday home in Shady Side?
The minimum age is normally 16, 18 or 21. It can change from property to property on Stayz, so look at the rules of your preferred Shady Side holiday home before making a booking.
How long can I rent a holiday home in Shady Side for?
The amount of time you can rent a Shady Side holiday home for depends on each property. Simply tap in your preferred travel dates to view options that offer extended stays. They come with all you require to make your extended break more comfortable and enjoyable, such as kitchens and air conditioning. Some properties may also offer weekly or monthly discounted prices, so you can stick around for longer for less.