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

Search the Best Cabins in Shady Side

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28
No exact matches found, but these alternatives could be just right

Recommended hotels in Shady Side

A two-story house with a front porch, a garage, and a driveway.

1. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
$413 nightly
The price is $415
Dec 1 - Dec 2
Total with taxes and fees
Sunset Cottage - West River Access and Views!
A house with a porch, surrounded by a well-maintained garden and a white fence.

2. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
$306 nightly
The price is $349
Nov 9 - Nov 10
Total with taxes and fees
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A hotel with a covered entrance, large columns, and a brick facade.

3. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.4 out of 10, Very good, (1,001 reviews)
"Great breakfast and hot tub"
United States
Marc
$95 nightly
The price is $108
Nov 22 - Nov 23
Total with taxes and fees
Holiday Inn Express & Suites Annapolis by IHG
A Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

4. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,060 reviews)
"I have stayed here before. Very nice hotel cause it is in a great location."
United States
Michael
$87 nightly
The price is $99
Nov 29 - Nov 30
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

5. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,000 reviews)
"The hotel is close to lots of shopping and dining options."
United States
FRANK
$101 nightly
The price is $115
Nov 29 - Nov 30
Total with taxes and fees
SpringHill Suites by Marriott Annapolis
A Best Western hotel with a modern facade, entrance with glass doors, and a parking area.

6. Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,001 reviews)
"Clean comfy bed"
United States
Dawnmarie
$79 nightly
The price is $90
Nov 22 - Nov 23
Total with taxes and fees
Best Western Annapolis
A multi-story hotel with a central entrance, a landscaped garden with flowers, and a metal sculpture.

7. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (522 reviews)
"Everything was great"
United States
sherman
$185 nightly
The price is $211
Dec 7 - Dec 8
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

8. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,270 reviews)
"Excellent staff & service!"
United States
Michele
$89 nightly
The price is $102
Nov 10 - Nov 11
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
A Sonesta ES Suites hotel with a brick facade, large windows, and a red awning.

9. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,006 reviews)
"Very quiet great location."
United States
Panagiotis
$83 nightly
The price is $95
Nov 29 - Nov 30
Total with taxes and fees
Sonesta ES Suites Annapolis
A multi-story hotel with a brick facade, large windows, and an American flag.

10. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,010 reviews)
"Great location"
United States
Jose
$103 nightly
The price is $117
Dec 6 - Dec 7
Total with taxes and fees
Crowne Plaza Annapolis by IHG
A historic brick building with a red roof, multiple windows, and a central staircase.

11. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,060 reviews)
"Great location, excellent stay"
United States
Christiaan
$106 nightly
The price is $120
Dec 3 - Dec 4
Total with taxes and fees
Historic Inns of Annapolis
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

12. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very good, (1,005 reviews)
"Great location, many shops, restaurants, the breakfast at this location is the best we experienced in many Hampton Inns. The lady that takes care of breakfast there is the best"
United States
Christopher
$88 nightly
The price is $100
Nov 17 - Nov 18
Total with taxes and fees
Hampton Inn & Suites Annapolis
A Hilton Garden Inn with a prominent entrance, multiple flags, and a well-maintained parking area.

13. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,002 reviews)
"The room was clean, the staff were wonderful, we didn't do breakfast and we were charged $8.00 a day for parking."
United States
Walter
$87 nightly
The price is $99
Nov 16 - Nov 17
Total with taxes and fees
Hilton Garden Inn Annapolis
A marina with boats docked at wooden piers, surrounded by greenery.

14. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (402 reviews)
"We are boaters so love the atmosphere of staying in a marina with a boat yard. The sunsets were beautiful there. Make sure you get a room facing the bay."
United States
Joan
$100 nightly
The price is $110
Nov 8 - Nov 9
Total with taxes and fees
Knapps Narrows Marina & Inn
A modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.

15. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,003 reviews)
"We good stay"
United States
Mike
$97 nightly
The price is $110
Nov 23 - Nov 24
Total with taxes and fees
Courtyard by Marriott Annapolis
A hotel with a modern design, featuring a mix of red and white facades, multiple windows, and a prominent entrance with arched doorways.

16. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,007 reviews)
"Great location, friendly staff."
United States
Joel
$98 nightly
The price is $111
Nov 22 - Nov 23
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown
A hotel with a modern design, featuring a mix of brick and siding exteriors, a covered entrance, and a parking area.

17. TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (143 reviews)
"It was AMAZING to stay there !!!"
United States
Nkusu Lauren
$101 nightly
The price is $115
Nov 22 - Nov 23
Total with taxes and fees
TownePlace Suites by Marriott Annapolis
A Candlewood Suites hotel with a central entrance, multiple floors, and a parking lot.

18. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (329 reviews)
"Good choice for a quick trip"
United States
Jose
$88 nightly
The price is $101
Nov 15 - Nov 16
Total with taxes and fees
Candlewood Suites Annapolis by IHG
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

19. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,010 reviews)
"Brunch was the best we had the whole trip! Excellent food and wonderful staff."
United States
REBECCA
$130 nightly
The price is $149
Nov 29 - Nov 30
Total with taxes and fees
Graduate by Hilton Annapolis
A modern hotel with a symmetrical facade, large windows, and a well-lit entrance.

20. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (250 reviews)
"Nice hotel"
United States
Imola
$127 nightly
The price is $145
Nov 15 - Nov 16
Total with taxes and fees
Fairfield Inn & Suites By Marriott 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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Would have loved water in the room."
Luschen 1-night trip
Posted 8 hours ago
Graduate by Hilton Annapolis

Find out more about Shady Side

Shady Side Cabin Rentals information

Number of reviews
6,434
Accommodation
0 Cabin Rentals
Lowest Price
$90
Highest Price
$415

Frequently asked questions

What are the best cabins near Shady Side?
Enjoy the great outdoors without giving up the comforts at one of our 29 cabins in and around Shady Side. Whether you have adventure or relaxation on your to-do list, Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay has both in spades. Alternatively, get cozy at Waterfront Ridge Retreat Cabin On St Jeromes Creek and soak up its postcard-worthy surroundings.
Are there cheap cabins in Shady Side?
Priced from $90 to $415 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?
Escape to a family cabin in or near Shady Side and top up the family photo album with some amazing new memories. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is a superb option. As well as the promise of fun-filled adventure, it comes with conveniences like a meal delivery service and a travel crib. Another family-friendly property is Lakefront Maryland Cabin With Fire Pit. A deck and a toaster will help keep your entourage happy.
What are the best hot tub cabins near Shady Side?
If you're the sort who considers a hot tub a must-have on vacation, you'll like Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. This charmer comes with lots of amenities to ensure a comfortable stay, including a firepit and a spa tub. Check out Elk River Cabin - 13 Acres, Water Views too. Another cabin with a hot tub near Shady Side, guests also have use of a king-sized bed and a firepit here.
What are the best cabins with pools near Shady Side?
Staying in a cabin rental with a pool adds a level of excitement to your vacation. If you're searching for one near Shady Side, Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay offers conveniences like a swimming pool and a patio to make your poolside escape even more enjoyable. Cabin - Maryland Vacation Rental With Private Pool And Dock is another favorite with travelers and features a swimming pool and a patio.
What are some great Shady Side cabins?
Surrounded by nature but still offering the comforts you need, you can't top a cabin if you're looking to truly enjoy the great outdoors. Waterfront Ridge Retreat Cabin On St Jeromes Creek is an ideal place to escape from the daily grind. Its amenities include a water view and a deck. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is another well-liked choice. A firepit and a fireplace will help make your stay even more enjoyable.
What are the best weekend cabin rentals in Shady Side?
Nothing's more relaxing than a weekend cabin getaway after a big week at work. Swap the office cubicle for two or three days in nature at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. A patio and a firepit are some of the amenities it comes with. Alternatively, clear away some cobwebs at Waterfront Ridge Retreat Cabin On St Jeromes Creek. Kick back here and make use of a patio and a firepit.
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 $90 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 log cabin filled with character. Get your adventure on or simply slow down and relax at 1850 Historic Log Cabin. Activities such as hiking and surfing are within easy reach here. Another attractive log cabin getaway is Tiny House / Log Cabin In Beautiful Wooded Urban Setting. Quad biking and parasailing will keep you busy when you're not kicking back in your comfy hideaway.
What are the highest-rated cabins in Shady Side?
With an impressive rating, it's no surprise why Waterfront Ridge Retreat Cabin On St Jeromes Creek is such a favorite with Expedia vacationers. Some amenities here include a patio and a firepit. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is another great option. Quality conveniences including a patio and a firepit will help you feel right at home.
Why should I book a cabin in Shady Side?
For a break that's big on charm, comfort and affordability, you can't beat a cabin. Leave your city blues behind and explore the greenery of the great outdoors. From days of rugged adventure to restful nights cuddled up by the fire, cabins offer the perfect mix of excitement and relaxation. Check out all the great Shady Side options right here on Expedia.

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