Shady Side Vacation Rentals

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Nov 30 - Dec 1
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Dec 12 - Dec 14

Vacation Rentals in Shady Side

Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Vacation Home in Shady Side

10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$376 nightly
The price is $429
Dec 1 - Dec 2
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Property grounds
Sunset Cottage - West River Access and Views!

Vacation Home in Shady Side

2.0 star property
$468 nightly
The price is $475
Dec 8 - Dec 9
Total with taxes and fees
Sunset Cottage - West River Access and Views!
Terrace/patio
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Houseboat in Arnold

10.0 out of 10, Exceptional, (5)
"Enjoyed the stay"
United States
Kedra B.
$321 nightly
The price is $366
Dec 2 - Dec 3
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Interior
Upscale Condo in Annapolis

Condo in Historic District

10.0 out of 10, Exceptional, (1)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
$471 nightly
The price is $536
Dec 17 - Dec 18
Total with taxes and fees
Upscale Condo in Annapolis
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

Vacation Home in Stevensville

9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
$246 nightly
The price is $261
Dec 1 - Dec 2
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Vacation Home in North Beach

10.0 out of 10, Exceptional, (16)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
$297 nightly
The price is $328
Dec 1 - Dec 2
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Cottage in North Beach

2.0 star property
10.0 out of 10, Exceptional, (2)
"So comfortable for the 2 of us. Close to restaurants, shopping, liquor store and to family in Chesapeake Beach. The 2nd BR let us spread out suitcases and extras. Stocked kitchen and bath. Grill right out the door to the fenced back yard. Driveway to the door. All we needed and felt at home. "
United States
Patricia M.
$261 nightly
The price is $277
Dec 1 - Dec 2
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Vacation Home in Stevensville

9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$240 nightly
The price is $254
Dec 1 - Dec 2
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby, sun loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Vacation Home in North Beach

10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$368 nightly
The price is $407
Dec 1 - Dec 2
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Smart TV, fireplace, books, printers
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Cottage in Stevensville

2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
$802 nightly
The price is $885
Dec 3 - Dec 4
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Outdoor pool
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Cottage in Owings

10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
$255 nightly
The price is $270
Dec 4 - Dec 5
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Apartment in Annapolis

10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
$363 nightly
The price is $414
Dec 1 - Dec 2
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Terrace/patio
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Vacation Home in Arundel on the Bay

9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
$401 nightly
The price is $457
Dec 1 - Dec 2
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Vacation Home in Grasonville

9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
$395 nightly
The price is $419
Dec 1 - Dec 2
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Fridge, microwave, oven, stovetop
All Star Annapolis Retreat - Walk to Stadium

Vacation Home in Admiral Heights

10.0 out of 10, Exceptional, (8)
"Beautiful and comfortable property! We enjoyed our time here and would book it again. "
United States
Paige R.
$622 nightly
The price is $662
Dec 2 - Dec 3
Total with taxes and fees
All Star Annapolis Retreat - Walk to Stadium
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in Annapolis

10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
$484 nightly
The price is $551
Dec 2 - Dec 3
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
Property grounds
New! Stylish downtown home w/awesome outdoor area!

Vacation Home in Stevensville

9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
$502 nightly
The price is $532
Dec 25 - Dec 26
Total with taxes and fees
New! Stylish downtown home w/awesome outdoor area!
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Vacation Home in Cape Saint Claire

9.8 out of 10, Exceptional, (11)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
$472 nightly
The price is $502
Dec 3 - Dec 4
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard
TV
Golden Anchor Retreat; Lux Living! - Sleeps 7

Vacation Home in Edgewater

10.0 out of 10, Exceptional, (2)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
$565 nightly
The price is $604
Dec 2 - Dec 3
Total with taxes and fees
Golden Anchor Retreat; Lux Living! - Sleeps 7
Marina
Cozy 2br home w/ parking in downtown Annapolis

Vacation Home in Historic District

10.0 out of 10, Exceptional, (72)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
$271 nightly
The price is $309
Dec 1 - Dec 2
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shady Side Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Evening bar staff was exceptional, as was the crew at the check-in desk. Excellent recommendations for places to eat. This hotel is within walking distance of everything we wanted to see and do. So much history here, cool stores, venues, and not far from the bay."
Jan Michael 2-night trip
Posted 8 hours ago
Hilton Garden Inn Annapolis Downtown

Find out more about Shady Side

Everything you need to know about Shady Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shady Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shady Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shady Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shady Side. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Shady Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $327 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shady Side rentals

At Expedia, we put the best Shady Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Shady Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shady Side vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shady Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Shady Side?

Yes, we have vacation rentals close to well known points of interest in Shady Side, or you can go with a more remote option if you're looking for relaxation. Shady Side is known for its shopping and restaurants. Make sure you have time to check out the parks and museums during your trip.

What are some of the best vacation rentals in Shady Side?

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA: This vacation home rental outside of Shady Side is located in the city center and offers a selection of games, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Shady Side?

Expedia has 11 vacation rentals for your stay in Shady Side.

What’s there to see and do in Shady Side?

Shadyside Park and Northern Chesapeake Bay are a couple of scenic spots to enjoy the outdoors, whereas Captain Avery Museum is one of the cultural attractions. Chesapeake Bay and Franklin Point State Park are other places to visit while you're in town.

What’s a vacation rental in Shady Side like?

Vacation rentals are private properties where you can stay for a couple of days or more in Shady Side. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a family getaway.