Top Shady Side Cabin Rentals

A river with boats, a marina, and a town with houses and buildings.

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Recommended hotels in Shady Side

DoubleTree by Hilton Hotel Annapolis

Annapolis

Marie

CA $182 total

includes taxes & fees

Aug 2 - Aug 3

Comfort Inn Conference Center

Bowie

Rafael

CA $174 total

includes taxes & fees

Aug 9 - Aug 10

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

Theresa

CA $182 total

includes taxes & fees

Jul 27 - Jul 28

SpringHill Suites by Marriott Annapolis

Annapolis

Zhun Wha

CA $206 total

includes taxes & fees

Jul 26 - Jul 27

Best Western Annapolis

Annapolis

Julian

CA $137 total

includes taxes & fees

Aug 2 - Aug 3

Hampton Inn & Suites Glenarden/Washington DC

Lanham

Favour

CA $168 total

includes taxes & fees

Aug 9 - Aug 10

Historic Inns of Annapolis

Historic District

Caitlin

CA $230 total

includes taxes & fees

Aug 16 - Aug 17

St Michaels Inn

St. Michaels

Ben

CA $143 total

includes taxes & fees

Aug 16 - Aug 17

Microtel Inn & Suites by Wyndham Gambrills

Gambrills

Erin

CA $154 total

includes taxes & fees

Aug 16 - Aug 17

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Thomas R.

CA $171 total

includes taxes & fees

Aug 3 - Aug 4

Crowne Plaza Annapolis by IHG

Annapolis

Jane

CA $189 total

includes taxes & fees

Aug 2 - Aug 3

Courtyard by Marriott Bowie

Bowie

Carol

CA $212 total

includes taxes & fees

Aug 3 - Aug 4

Hampton Inn & Suites Annapolis

Annapolis

Marie

CA $156 total

includes taxes & fees

Jul 23 - Jul 24

Hilton Garden Inn Annapolis

Annapolis

Paul

CA $163 total

includes taxes & fees

Aug 18 - Aug 19

Best Western Kent Narrows Inn

Grasonville

Brenda

CA $178 total

includes taxes & fees

Jul 27 - Jul 28

Knapps Narrows Marina & Inn

Sherwood

Polina

CA $231 total

includes taxes & fees

Jul 20 - Jul 21

Hyatt Place Kent Narrows & Marina

Grasonville

Uri

CA $263 total

includes taxes & fees

Jul 26 - Jul 27

Candlewood Suites Annapolis by IHG

Annapolis

Mehran

CA $147 total

includes taxes & fees

Jul 27 - Jul 28

Quality Inn Grasonville near Kent Island

Grasonville

Carol

CA $156 total

includes taxes & fees

Aug 18 - Aug 19

Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Keri

CA $154 total

includes taxes & fees

Aug 2 - Aug 3

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Top Shady Side Hotel Reviews

Historic Inns of Annapolis

10/10 Excellent

"Nice staff"

Rod 'N' Reel Resort

8/10 Good

"Pretty cool place. Great views. A disclosure needs to be made that rooms are adjoining. Saw the door but was not informed at check-in. Made us a little uncomfortable. There isn't actual beach access on the property but a short drive away there is. We thought we were going to enjoy relaxing at the beach in the evening but after 6pm it is only for Calvert County residents. Also alot of the fishing spots are not in the area anymore. The closest we found at North Beach Pier was a small fee for non-residents but free after 6pm. Bring a hat or umbrella, there is no shaded area. Another note the North Tower is more updated and kept up. The South Tower was okay but we noticed the difference in dated items like the elevators, ice machine, etc. We even noticed the elevators on the South Tower has the same spill while the elevators on the North Tower had Wet Floor signs multiple times a day from being cleaned. Lastly, the South Tower only has ice machines on the 2nd and 4th floors with a microwave on the 1st floor but the North Tower has these on every floor. Didn't like the idea of a shared microwave as there were many smells and seasoning of food."

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"The hotel is lovely and right in the heart of everything. We walked to each meal and walked even further for exercise. The room was clean and had all that we needed aside from some missing toiletries. As busy as the hotel was, the noise was contained and did not bother us. Overall a great stay and we will definitely choose this hotel in the future."

Find out more about Shady Side

Shady Side Cabin Rentals information

Number of reviews	12,080
Accommodation	0 Cabin Rentals
Lowest Price	CA $137
Highest Price	CA $263

Frequently asked questions

What are the best cabins near Shady Side?

Immerse yourself in the outdoors without forgoing the comforts at one of our 29 cabins in and around Shady Side. Whether you have relaxation or adventure on your mind, Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay offers both. Alternatively, spend your vacation at Waterfront Ridge Retreat Cabin On St Jeromes Creek and nestle yourself among picturesque surroundings.

Are there cheap cabins in Shady Side?

Priced from CA $137 to CA $263 per night, escaping the ordinary has never been so affordable. Secure one of our cheap cabins in Shady Side and experience the great outdoors without putting a dent in your budget.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

What are the best family cabins near Shady Side?

If you're on the lookout for a vacation your little adventurers will go wild for, a family cabin in or near Shady Side is a fantastic choice. Make new memories together at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. It offers a meal delivery service and a travel crib on top of outdoor adventure. Lakefront Maryland Cabin With Fire Pit is also perfect for small groups or families and comes with a deck and a toaster.

What are the best hot tub cabins near Shady Side?

If you're the type who can't live without a hot tub on vacation, you'll like Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. This knockout comes with plenty of amenities to ensure a comfortable stay, including a firepit and a spa tub. Look up Elk River Cabin - 13 Acres, Water Views as well. Another cabin with a hot tub near Shady Side, you'll also have use of a king-sized bed and a firepit here.

What are the best cabins with pools near Shady Side?

Slip on your swimwear and go for a few laps whenever you like when you stay at one of our cabin rentals with a pool near Shady Side. Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay is a favourite. A swimming pool and a patio are some of the other amenities you'll find here. Alternatively, take some time out at Cabin - Maryland Vacation Rental With Private Pool And Dock. As well as a pool, this cabin comes with a swimming pool and a patio.

What are some great Shady Side cabins?

Nestled in nature but with the conveniences of home, nothing tops a cabin if you'd love to truly experience the great outdoors. Waterfront Ridge Retreat Cabin On St Jeromes Creek is the perfect place to get away from it all. Amenities here include a water view and a deck. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is another welcoming property. A firepit and a fireplace will help make your stay nice and comfy.

What are the best weekend cabin rentals in Shady Side?

If you want to spend a couple of relaxing days immersed in nature, Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay awaits. Stay here for a weekend and make use of conveniences including a patio and a firepit. Another superb property is Waterfront Ridge Retreat Cabin On St Jeromes Creek. Offering a patio, a firepit and plenty of chill vibes, you'll go home feeling refreshed and rejuvenated.

What are the best cabin prices in Shady Side?

If you're eager to save a few dollars on your stay, Expedia has some great deals on Shady Side cabins that won't put a hole in your wallet. How does CA $137 a night sound?

Can I find log cabins in Shady Side?

For lots of nature lovers, the ideal outdoor vacation isn't complete without bunking down in a character-filled log cabin. Get out and active or simply slow down and relax at 1850 Historic Log Cabin. Recreational activities such as shore fishing and hiking are within easy reach here. Another log cabin getaway is Tiny House / Log Cabin In Beautiful Wooded Urban Setting. Hiking and picnicking will keep you busy when you're not chilling in your comfy hideaway.

What are the highest-rated cabins in Shady Side?

Expedia travellers keep coming back to Waterfront Ridge Retreat Cabin On St Jeromes Creek. This superb option offers lots of handy amenities like a patio and a firepit. It won't take you very long to see why Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is also a hit with vacationers. Conveniences like a patio and a firepit will help make your stay even more comfortable.

Why should I book a cabin in Shady Side?

Affordability, comfort, rustic charm — there are loads of reasons to opt for a Shady Side cabin. Get away from the noise of the concrete jungle and hear the sounds of birds and nature instead. There's so much adventure right on your doorstep too. Whether you're vacationing with friends, family or your partner, you'll find the perfect rental cabin on Expedia.

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Edgewater Vacation Rentals

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Find Cabins in Shady Side for Rent from CA $137

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Shady Side

DoubleTree by Hilton Hotel Annapolis

Comfort Inn Conference Center

Country Inn & Suites by Radisson, Annapolis, MD

SpringHill Suites by Marriott Annapolis

Best Western Annapolis

Hampton Inn & Suites Glenarden/Washington DC

Historic Inns of Annapolis

St Michaels Inn

Microtel Inn & Suites by Wyndham Gambrills

Holiday Inn Express Annapolis East-Kent Island by IHG

Crowne Plaza Annapolis by IHG

Courtyard by Marriott Bowie

Hampton Inn & Suites Annapolis

Hilton Garden Inn Annapolis

Best Western Kent Narrows Inn

Knapps Narrows Marina & Inn

Hyatt Place Kent Narrows & Marina

Candlewood Suites Annapolis by IHG

Quality Inn Grasonville near Kent Island

Holiday Inn Express & Suites Annapolis by IHG

Find vacation rentals that suit your style

Top Shady Side Hotel Reviews

Historic Inns of Annapolis

Find out more about Shady Side

Shady Side Cabin Rentals information

Frequently asked questions

Explore a world of travel with Expedia