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Villas in Shady Side

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Find the right villa for you in Shady Side

The best villas in Shady Side

Check out our selection of great villas in Shady Side

Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment

Upper Marlboro (Near Shady Side)

12 miles from Addison Road-Seat Pleasant in Upper Marlboro, Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment features accommodations with access to a fitness room.

A
Aimee
From
United States
The location was perfect for what we needed. Also easy access to anything we needed.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 17 reviews
Price from
$191.23
1 night, 2 adults

Londontowne Hideaway

Annapolis (Near Shady Side)

Londontowne Hideaway is located in Annapolis, just 6.8 miles from Annapolis Yacht Basin and 8.5 miles from Annapolis Landing Marina.

J
Julia
From
United States
beds were SUPER comfy and house was very clean
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 5 reviews
Price from
$469.71
1 night, 2 adults

Stylish + fresh bungalow 2 blocks from N-MC Stadium

Annapolis (Near Shady Side)

Just a 11-minute walk from Navy-Marine Corps Memorial Stadium and 1.2 miles from Whitehall Gallery, Stylish + fresh bungalow 2 blocks from N-MC Stadium features accommodations in Annapolis with a...

B
Big Mac
From
United States
The home was completely updated and decorated so cute. It was like a beach cottage. We had everything we needed to cook to include spices and oil. Plenty of extra linens and towels. The neighborhood was extremely quiet and peaceful.
Scored out of 10, guest rating 7.2
Good - What previous guests thought, 11 reviews
Price from
$500.50
1 night, 2 adults

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Shady Side

Steps to Chesapeake Bay! 'Callaway Drive Retreat' offers accommodations in Shady Side, 20 miles from Maryland State House Of Delegates and 20 miles from Annapolis Yacht Basin.

S
Shenae
From
United States
It was very comfortable and located in a very serene area
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 8 reviews

Vanishing Run Retreat with Pool

Harwood (Near Shady Side)

Vanishing Run Retreat with Pool is located in Harwood, just 14 miles from Annapolis Harbor and 13 miles from Six Flags America. This property offers a private pool and free private parking.

R
Rita
From
United States
Clean, comfortable and great location! Close to everything but quiet and like home! Beautiful kitchen with everything you needed. Bathrooms updated and beds are comfy!
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 6 reviews

Searenity Stays

Edgewater (Near Shady Side)

Searenity Stays is located in Edgewater, just 12 miles from Maryland State House Of Delegates and 12 miles from Annapolis Yacht Basin.

J
Jennifer
From
United States
Perfect cottage get away. Hosts thought of everything we could possibly need. Great for families and not far from beaches and restaurants.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 9 reviews

8 Bells Bungalow - Cozy, Stylish, Prime Location

Annapolis (Near Shady Side)

8 Bells Bungalow - Cozy, Stylish, Prime Location is located in Annapolis, just 2.2 miles from Annapolis Harbor and 24 miles from Inner Harbor.

L
Lazer Joseph
From
United States
Excellent host and stay.. Thank you..
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 5 reviews

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville (Near Shady Side)

Relax on Kent Island in 3 Bedroom Home w/Waterview is located in Stevensville, just 22 miles from Annapolis Harbor and 14 miles from Sandy Point State Park.

S
Steven
From
United States
Comfortable and convenient location.
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 7 reviews

Walk to the stadium, downtown, West St - close to everything

Annapolis (Near Shady Side)

Walk to the stadium, downtown, West St - close to everything offers accommodations in Annapolis, 2 miles from Annapolis Harbor and 1.3 miles from Annapolis Yacht Basin.

B
Brittany
From
United States
The property owner was very attentive, thoughtful, and very accessible. They truly thought about every possible need that we could use or needed. Had drinks ready in the fridge, snacks. It was like we were at home. Cozy and spacious, everyone had their own space, but amazing common area. Very close to everything. I’m absolutely in love with this property.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 10 reviews

Historic Row Home 1 Block from Gate 1 at USNA

Annapolis (Near Shady Side)

1.1 miles from Annapolis Harbor in Annapolis, Historic Row Home 1 Block from Gate 1 at USNA offers accommodations with access to a hot tub.

V
Venus
From
United States
The location was excellent. The house was very modern, clean, and had all of the amenities that you would want or need.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 6 reviews
All villas in Shady Side

Looking for a villa?

Perfect for families, groups, or couples who enjoy luxury and independence while traveling. Enjoy the space and privacy of these fully-furnished, free-standing mansions – travelers can cook, lounge, and explore at their own pace. Note that in Bali, a resort will also be called a villa.

Most booked villas in Shady Side and surrounding area in the past month

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Popular with guests booking villas in Shady Side

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 8 reviews

Popular with guests booking villas in Shady Side

Popular with guests booking villas in Harwood

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 6 reviews

Popular with guests booking villas in Edgewater

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking villas in Deale

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Popular with guests booking villas in Edgewater

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 9 reviews

Popular with guests booking villas in Tracys Landing

Great access to the city center. Check these villas in Shady Side and nearby

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Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 8 reviews

Guest review
It was very comfortable and located in a very serene area
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 9 reviews

Guest review
The location was nice and quiet. The house was very clean and the owner was very nice and caring. We will be visiting again very soon.
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

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