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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Shady Side cottages

Exterior

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (908 reviews)
"Breakfast menu had a great variety and was fresh. "
United States
Timothy
The price is RM420
RM466 total
includes taxes & fees
1 Jun - 2 Jun
Quality Inn Grasonville near Kent Island
Exterior

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,005 reviews)
"It is a nice Hotel."
United States
Dale
The price is RM455
RM505 total
includes taxes & fees
31 May - 1 Jun
Best Western Kent Narrows Inn
Exterior

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,087 reviews)
"Breakfast was great"
United States
Sean
The price is RM388
RM442 total
includes taxes & fees
31 May - 1 Jun
Microtel Inn & Suites by Wyndham Gambrills
Exterior

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,011 reviews)
"Older Hotel but clean and staff was great."
United States
Gregory
The price is RM354
RM404 total
includes taxes & fees
3 Jun - 4 Jun
Best Western Annapolis
Balcony view

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,006 reviews)
"Nice location "
United States
Duan
The price is RM533
RM671 total
includes taxes & fees
25 May - 26 May
Rod 'N' Reel Resort
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
"Very nice room and wonderful stay."
United States
Julie
The price is RM586
RM784 total
includes taxes & fees
26 May - 27 May
Kent Island Resort
Exterior

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,002 reviews)
"Breakfast was excellent and parking was convenient and safe"
United States
Paul
The price is RM353
RM402 total
includes taxes & fees
27 May - 28 May
Hilton Garden Inn Annapolis
Exterior

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (248 reviews)
"Great stay in a quiet area"
United States
Mehran
The price is RM415
RM493 total
includes taxes & fees
7 Jun - 8 Jun
Candlewood Suites Annapolis by IHG
View from property

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,002 reviews)
"We had a lovely stay and would go back again! Pleasant staff and a short ride to everything."
United States
JoAnn
The price is RM512
RM563 total
includes taxes & fees
5 Jun - 6 Jun
St Michaels Inn
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,004 reviews)
"We were very pleased with our overnight here - it was economical and more than sufficient. It was clean, comfortable and it was nice to have breakfast included (try the cinnamon buns!) "
United States
Susan
The price is RM530
RM588 total
includes taxes & fees
7 Jun - 8 Jun
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,006 reviews)
"Had a very nice stay"
United States
Laura
The price is RM394
RM445 total
includes taxes & fees
8 Jun - 9 Jun
Comfort Inn Conference Center
Exterior

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, (1,012 reviews)
"Great location with good breakfast. 👍"
United States
David
The price is RM408
RM465 total
includes taxes & fees
8 Jun - 9 Jun
Country Inn & Suites by Radisson, Annapolis, MD
Garden

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,008 reviews)
"Great stay!"
United States
Jehane
The price is RM453
RM516 total
includes taxes & fees
26 May - 27 May
DoubleTree by Hilton Hotel Annapolis
Exterior

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,009 reviews)
"Wonderful place to stay!"
United States
Michele
The price is RM392
RM446 total
includes taxes & fees
27 May - 28 May
Sonesta ES Suites Annapolis
Front of property

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (444 reviews)
"Wonderful rooms and many amenities."
United States
Gene
The price is RM906
RM1,083 total
includes taxes & fees
10 Jun - 11 Jun
The Wildset
Exterior

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,028 reviews)
"Great location, pet-friendly with a very welcoming staff."
United States
Lisa
The price is RM506
RM577 total
includes taxes & fees
31 May - 1 Jun
Hilton Garden Inn Annapolis Downtown
View from property

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (486 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is RM941
RM1,073 total
includes taxes & fees
21 May - 22 May
Anchored Inn at Hidden Harbour Marina
Exterior

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,001 reviews)
"Beautiful area"
United States
Dan
The price is RM610
RM677 total
includes taxes & fees
15 Jun - 16 Jun
Hilton Garden Inn Kent Island Marina
Porch

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (134 reviews)
"We really enjoyed our stay at The Parsonage. The property and room were kept well. The staff were sweet and attentive. Very good location as far as walking distance to shops, restaurants and the waterfront area. I would certainly return and certainly recommend to anyone visiting St. Michael’s. "
United States
Katie
The price is RM989
RM1,088 total
includes taxes & fees
20 May - 21 May
Parsonage Inn
Exterior

Executive Inn And Suites

Executive Inn And Suites
2.0 star property
Upper Marlboro
7.2 out of 10, Good, (576 reviews)
"Clean and accommodating staff."
United States
Annette
The price is RM413
RM467 total
includes taxes & fees
20 May - 21 May
Executive Inn And Suites
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

The Westin Annapolis

The Westin Annapolis

6/10 Okay
"The bar staff and cleaning staff were very kind. The front desk attendants seemed to be unhappy, though I did have one attendant in particular who was very helpful. The hotel rooms themselves were not as nice as most Westins. They were akin to a Hampton Inn which- for the price per night- seems rather absurd. The valet staff were great and timely as well. Overall a good stay and the location is nice. For the price though, I’d prefer to stay by the water next time."
AnnMarie 2-night trip
Posted 4 hours ago
The Westin Annapolis

Find out more about Shady Side

Shady Side Cottages information

Number of reviews
13,963
Accommodation
33 Cottages
Lowest Price
RM402
Highest Price
RM1,088

Frequently asked questions

How much do cottages in Shady Side cost?
Cottages in Shady Side range between RM402 and RM1,088 per night. These retreats offer a chance to get reacquainted with nature — at a price you can afford. 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.
Why book your cottage in Shady Side with Expedia?
Reserving a cottage in Shady Side is as simple as deciding on your travel dates and choosing your ideal place for a getaway in nature. From upscale retreats to affordable stays and cottages that include perks like a pool, Expedia has something for all styles. As for epic deals? We've got them as well!
How can I find cheap cottages in Shady Side?
Expedia is here to help you locate cheap cottages in Shady Side. To book a fantastic stay in a few quick clicks, use our handy filter tool to refine your search results by amenities, star rating and budget.
What is there to do in Shady Side near my cottage?
If you're ready to discover the best of Shady Side, find your way to Shadyside Park. It's a hit among locals and tourists alike.

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