Search Vacation Homes in Shady Side

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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Vacation Homes in Shady Side

The Blue Crab Beach House - Free beach passes
Beach nearby, sun loungers, beach towels

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (57)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Marina

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (220)
"Perfect Location - Easy Process - Comfortable Home!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Dollhouse in Central Historic St Michaels
Exterior

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (49)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (28)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Dining

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

10.0 out of 10, Exceptional, (102)
"Had a wonderful, peaceful stay."
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Fridge, microwave, oven, stovetop

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (25)
"Great location for our team to stay during Annapolis sail show. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Fridge, microwave, oven, stovetop

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

9.6 out of 10, Exceptional, (12)
"Wonderful location and just perfect for our family! "
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Fridge, microwave, oven, stovetop

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.8 out of 10, Exceptional, (20)
"Loved the stay, easy and functional for a larger group to get together in Annapolis. "
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Adorable waterside cottage with pool Beach community
Outdoor pool

Adorable waterside cottage with pool Beach community

9.4 out of 10, Exceptional, (39)
"This was a wonderful place to stay! My husband, dog, and I enjoyed our time, the pool and location near the beach were wonderful."
Adorable waterside cottage with pool Beach community
PERFECT LOCATION in the heart of history
Exterior

PERFECT LOCATION in the heart of history

10.0 out of 10, Exceptional, (201)
"Great weekend at this property in Annapolis! Location is within walking distance to restaurants and shopping!"
PERFECT LOCATION in the heart of history
Downtwn Stylish 3BR/2BA with Exclusive Parking in Annapolis-USNA Stadium
Fridge, microwave, oven, stovetop

Downtwn Stylish 3BR/2BA with Exclusive Parking in Annapolis-USNA Stadium

9.2 out of 10, Wonderful, (7)
"Nice property and good location to visit historic Annapolis. Nice to have parking on the property"
Downtwn Stylish 3BR/2BA with Exclusive Parking in Annapolis-USNA Stadium
Beach Home with King Bed and Beach Passes in a Cute Town
Beach nearby

Beach Home with King Bed and Beach Passes in a Cute Town

10.0 out of 10, Exceptional, (11)
"We had everything we needed in this townhome in North Beach. Nicely decorated, clean and the beds were comfortable! Perfect spot for our girl's weekend."
The price is SAR 620
SAR 1,589 total
includes taxes & fees
22 Jun - 23 Jun
Beach Home with King Bed and Beach Passes in a Cute Town
Rising Sun Bay View Cottage
Terrace/patio

Rising Sun Bay View Cottage

Rising Sun Bay View Cottage
Private Cottage on gated estate
Property grounds

Private Cottage on gated estate

10.0 out of 10, Exceptional, (24)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Fridge, microwave, oven, stovetop

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.8 out of 10, Exceptional, (8)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is SAR 3,996
SAR 6,181 total
includes taxes & fees
23 Jun - 24 Jun
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Wright's Cottage- Pet's Welcome & EV Charging
TV, offices

Wright's Cottage- Pet's Welcome & EV Charging

9.8 out of 10, Exceptional, (11)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
The price is SAR 525
SAR 1,506 total
includes taxes & fees
26 Jun - 27 Jun
Wright's Cottage- Pet's Welcome & EV Charging
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Beach nearby

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (61)
"We had a wonderful stay at this property and would return in the future. Thank you!"
Recently Renovated Annapolis Home - Conveniently Located
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Property grounds

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.8 out of 10, Exceptional, (81)
"This is a great location The house is clean and updated. We enjoyed and would stay here again."
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Cozy Annapolis Cottage
Terrace/patio

Cozy Annapolis Cottage

10.0 out of 10, Exceptional, (9)
"We're in the process of selling our home and used this place as our home away from home while the listing went live. It was cozy and had everything that we needed to feel like we could rest up after the difficult process of prepping our house. And a safe, fenced in yard for our dogs. It was perfect, thank you! "
Cozy Annapolis Cottage
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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