Shady Side Vacation Rentals from $233: Search Short-Term Rentals

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Our top choices for Shady Side vacation rentals

1. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

Joshua T.

$323 nightly

Aug 30 - Aug 31

Total with taxes and fees

2. Sunset Cottage - West River Access and Views!

Shady Side

Marci M.

$536 nightly

Sep 9 - Sep 10

Total with taxes and fees

3. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Deale

Maude H.

$264 nightly

Aug 17 - Aug 18

Total with taxes and fees

4. Family Home on Mayo Peninsula | Deck | Sleeps 10

Edgewater

Kristin G.

$621 nightly

Aug 16 - Aug 17

Total with taxes and fees

5. Charming Annapolis WaterVIEW Home

Arundel on the Bay

Whitney M.

$617 nightly

Sep 9 - Sep 10

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

6. Renovated Bungalow | Walk to Beach | Dog-Friendly

Edgewater

Diane D.

$520 nightly

Sep 1 - Sep 2

Total with taxes and fees

7. Londontowne Home | Beach | 3BR

Edgewater

Sam A.

$654 nightly

Aug 16 - Aug 17

Total with taxes and fees

8. Londontowne Rancher | 3BR | Near Waterfront

Edgewater

"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "

rebekah h.

$621 nightly

Aug 18 - Aug 19

Total with taxes and fees

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Top Shady Side Hotel Reviews

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Staff was extremely kind and helpful."

St Michaels Inn

10/10 Excellent

"When we arrived at breakfast, there really wasn’t a selection of anything healthy. No hot food at all. We were told by another guest that there was no hot food on Monday and Tuesday. Would have thought that would’ve been mentioned by hotel staff. The rooms were clean and our interaction with staff was pleasant. However, we skipped breakfast both days we stayed here and ate at a restaurant down the road. "

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

10/10 Excellent

"This property was in a central location to lots of places. I did think there was going to be a larger beach that you could go to within the community, however it was a very enjoyable stay. The hostess was sweet and the house is adorable."

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

10/10 Excellent

"We stayed here while my son went to summer camp at USNA and enjoyed the peaceful neighborhood. A couple hiccups occurred at the beginning of the trip but Charles was very open to resolving them with open and timely communication. The kids LOVED having the bikes to ride around the neighborhood and the beach is quiet with a lot of rocks for the kids to play on. The park area for the neighborhood has the most beautiful sunrises. We went into DC some to see the sites and it made for an easy drive to the metro station to get into the city. It was so nice to be able to come back to a peaceful cottage after a day in the city. The house is stocked with anything you would need in the kitchen to make for a comfortable stay. Would stay again if the opportunity arises!"

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 $233 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.

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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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This vacation home rental outside of Shady Side is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Shady Side?

Expedia has 13 vacation rentals for your stay in Shady Side.

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

Northern Chesapeake Bay and Chesapeake Bay are a couple of scenic spots to enjoy the outdoors, whereas Captain Avery Museum is one of the cultural attractions. Shadyside Park 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.

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Check prices for these dates

Our top choices for Shady Side vacation rentals

1. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

2. Sunset Cottage - West River Access and Views!

3. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

4. Family Home on Mayo Peninsula | Deck | Sleeps 10

5. Charming Annapolis WaterVIEW Home

6. Renovated Bungalow | Walk to Beach | Dog-Friendly

7. Londontowne Home | Beach | 3BR

8. Londontowne Rancher | 3BR | Near Waterfront

9. Annapolis Retreat - 7 mins from downtown Annapolis!

10. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

11. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

12. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

13. Eastport 3 bedroom Cottage: Walk to Downtown

14. Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

15. Beachside Oasis with Beach Passes & King Suite by A Haven Away

16. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

17. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

18. Historic Downtown 3BR Crabby Patty-∙Walk to USNA

19. Dean Street's Lower Deck House!

Find vacation rentals that suit your style

Top Shady Side Hotel Reviews

Hyatt Place Kent Narrows & Marina

Comfort Inn Conference Center

St Michaels Inn

Country Inn & Suites by Radisson, Annapolis, MD

Graduate by Hilton Annapolis

Comfort Inn Largo-Washington DC East

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Find out more about Shady Side

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