Search the Best Cabins in Shady Side

Start date: Check-in selected.
To Date
End date: Check-out

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 24 - Oct 26
In two months
Dec 5 - Dec 7
In three months
Jan 2 - Jan 4
In four months
Jan 30 - Feb 1

Cabin Rentals in Shady Side

We don't have any properties that match your exact search
See all properties in Shady Side

Recommended hotels in Shady Side

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

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

10.0 out of 10, Exceptional, (2)
"The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side."
$375 nightly
The price is $428
Oct 13 - Oct 14
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
St Michaels Inn
View from property

St Michaels Inn

2.5 star property
8.2 out of 10, Very Good, (1007)
"Great location, free parking, free breakfast excellent staff."
$92 nightly
The price is $102
Oct 22 - Oct 23
Total with taxes and fees
St Michaels Inn
Knapps Narrows Marina & Inn
Front of property

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (342)
"Beautiful view!"
$100 nightly
The price is $110
Oct 14 - Oct 15
Total with taxes and fees
Knapps Narrows Marina & Inn
Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1846)
"Perfect location…terrific staff…spacious room with a king sized bed! "
$145 nightly
The price is $166
Nov 2 - Nov 3
Total with taxes and fees
Historic Inns of Annapolis
Country Inn & Suites by Radisson, Annapolis, MD
Exterior

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1009)
"Great place to stay Friendly staff secure rooms Thank you "
$97 nightly
The price is $110
Nov 2 - Nov 3
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
Hilton Garden Inn Annapolis Downtown
Exterior

Hilton Garden Inn Annapolis Downtown

3.0 star property
8.6 out of 10, Excellent, (1004)
"Good central location "
$100 nightly
The price is $114
Nov 3 - Nov 4
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown
Quality Inn
Exterior

Quality Inn

2.5 star property
7.8 out of 10, Good, (839)
"Great place and great staff"
$98 nightly
The price is $109
Nov 2 - Nov 3
Total with taxes and fees
Quality Inn
Comfort Inn Conference Center
Exterior

Comfort Inn Conference Center

2.5 star property
9.2 out of 10, Wonderful, (1009)
"Very clean, easy check in (checked in around 11:30pm), quiet, and excellent breakfast "
$99 nightly
The price is $112
Oct 20 - Oct 21
Total with taxes and fees
Comfort Inn Conference Center
Crowne Plaza Annapolis by IHG
Exterior

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1002)
"Good location"
$100 nightly
The price is $114
Nov 3 - Nov 4
Total with taxes and fees
Crowne Plaza Annapolis by IHG
Graduate by Hilton Annapolis
Exterior

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1005)
"Great area and it was a perfect hotel for our trip. "
$155 nightly
The price is $177
Nov 10 - Nov 11
Total with taxes and fees
Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Largo/Washington DC
Exterior

DoubleTree by Hilton Hotel Largo/Washington DC

4.0 star property
8.0 out of 10, Very Good, (1022)
"The staff at the hotel was very friendly and helpful, highly recommended for everyone that like this area. "
$94 nightly
The price is $107
Nov 3 - Nov 4
Total with taxes and fees
DoubleTree by Hilton Hotel Largo/Washington DC
Best Western Annapolis
Exterior

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1008)
"Great place."
$79 nightly
The price is $90
Nov 9 - Nov 10
Total with taxes and fees
Best Western Annapolis
Microtel Inn & Suites by Wyndham Gambrills
Exterior

Microtel Inn & Suites by Wyndham Gambrills

2.0 star property
9.0 out of 10, Wonderful, (1011)
"The location provided many dining and shopping options within a short walk. Staff was attentive and friendly. Great stay!"
$84 nightly
The price is $96
Nov 3 - Nov 4
Total with taxes and fees
Microtel Inn & Suites by Wyndham Gambrills
Hilton Garden Inn Annapolis
Exterior

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very Good, (1007)
"Our stay at the hotel was easy check in and check out. Quiet and great location for our stay."
$92 nightly
The price is $104
Nov 2 - Nov 3
Total with taxes and fees
Hilton Garden Inn Annapolis
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (906)
"Nice Holiday Inn Express with great water views."
$119 nightly
The price is $132
Nov 10 - Nov 11
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Rod 'N' Reel Resort
Exterior

Rod 'N' Reel Resort

4.0 star property
8.4 out of 10, Very Good, (1001)
"Great place to stay."
$147 nightly
The price is $161
Oct 19 - Oct 20
Total with taxes and fees
Rod 'N' Reel Resort
The Wildset
Exterior

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (386)
"fantastic location, great bouboun selection at the bar and wonderful staff"
$239 nightly
The price is $263
Oct 13 - Oct 14
Total with taxes and fees
The Wildset
Inn at Perry Cabin
Exterior

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (365)
"Beautiful place to stay."
$445 nightly
The price is $489
Nov 12 - Nov 13
Total with taxes and fees
Inn at Perry Cabin
The Tilghman Island Inn
Front of property

The Tilghman Island Inn

3.5 star property
9.6 out of 10, Exceptional, (114)
"Great staff and food!"
$200 nightly
The price is $220
Nov 2 - Nov 3
Total with taxes and fees
The Tilghman Island Inn
Holiday Inn Express & Suites Annapolis by IHG
Exterior

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very Good, (1000)
"Great location. "
$107 nightly
The price is $122
Oct 29 - Oct 30
Total with taxes and fees
Holiday Inn Express & Suites Annapolis by IHG
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shady Side Hotel Reviews

Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"Warm greeting on entry. Nice, clean room. Exceeded my expectations."
Arthur 1-night trip
Posted 2 days ago
Comfort Inn Conference Center

Find out more about Shady Side

Shady Side Cabin Rentals information

Number of reviews
16,850
Accommodation
1 Cabin Rentals
Lowest Price
$90
Highest Price
$489

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 $489 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.

Explore a world of travel with Expedia