Vacation Homes in Shady Side, MD

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Top Vacation Homes in Shady Side

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

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

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A gym is featured at this vacation home, along with limo/town car service and a garden. Laundry facilities, concierge services, and barbecue grills are also on offer.
Pool
Kitchen
Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood

$307 nightly
The price is $350 total per night
$350 total
Oct 1 - Oct 2
Total with taxes and fees
This vacation home includes a garden and laundry facilities.
Kitchen
Washer
The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

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This vacation home includes a garden and barbecue grills.
Kitchen
Air conditioning
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

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This vacation home features a water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Riverfront Retreat 7mil from MD Renaissance Fest!

Riverfront Retreat 7mil from MD Renaissance Fest!

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A gym is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Luxury Waterfront Executive Family Home Annapolis with All Amenities

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This vacation home features a gym and a hot tub. Laundry facilities and barbecue grills are also provided.
Hot Tub
Washer
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

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An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site.
Pool
Kitchen
Charming Historic Townhouse Steps From USNA

Charming Historic Townhouse Steps From USNA

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This vacation home features laundry facilities.
Kitchen
Washer
Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

$304 nightly
The price is $347 total per night
$347 total
Sep 10 - Sep 11
Total with taxes and fees
A garden, express check-in, and express check-out are available at this vacation home. Laundry facilities are provided for your convenience.
Kitchen
Washer
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

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

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This vacation home features laundry facilities.
Kitchen
Washer
Beautiful 2-bedroom water view house in Annapolis

Beautiful 2-bedroom water view house in Annapolis

Annapolis, MD
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This vacation home features laundry facilities.
Washer
Dryer
3-bedroom house in Gambrills, in the area of Annapolis, Baltimore, & DC.

3-bedroom house in Gambrills, in the area of Annapolis, Baltimore, & DC.

Gambrills, MD
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This vacation home features laundry facilities.
Washer
Dryer
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See all available properties in Shady Side
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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.

Top hotels in Shady Side

DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

9100 Basil Court, Upper Marlboro, MD
$122 nightly
The price is $138 total per night from Sep 29 to Sep 30
$138 total
Sep 29 - Sep 30
Total with taxes and fees

Find the Best Vacation Homes in Shady Side

Why book a vacation home in Shady Side?

Vacation homes in Shady Side make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.

How much is a vacation home in Shady Side?

Private Shady Side rental homes range between $92 - $350 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.

What are the cancellation and flexibility options on Travelocity?

To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.

What amenities should I look out for in a vacation home?

There are some exciting amenities available in Shady Side vacation home rentals. You might look for Shady Side rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room. 

Vacation rentals in Shady Side offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.

When is the best time to rent a vacation home in Shady Side?

You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.

Why book a vacation home with Travelocity?

Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Shady Side. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Shady Side hotels and vacation homes that best suit your stay. We also have deals for flights, and Shady Side car rentals. You’ll save even more when you bundle your items into a Shady Side vacation package!

How many vacation homes are available to book in Shady Side?

There are 654 rental homes in Shady Side. Enter your travel dates to check availability.

How do I find the best price for a vacation home in Shady Side?

Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.

Shady Side Vacation Homes essential information

Accommodation
654 Vacation Homes
Lowest Price
$92
Highest Price
$350
Popular accommodation
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Large 2 bedroom house with private parking in a nice neighborhood, The Cozy Crab- Your Charming Haven in Lovely North Beach!, 240' Private Beachfront @Kent Island Love Point - Great for Large Groups, Riverfront Retreat 7mil from MD Renaissance Fest!, Luxury Waterfront Executive Family Home Annapolis with All Amenities, RANCH AT ROYAL OAK- Exclusive waterfront pool pier, Charming Historic Townhouse Steps From USNA, Cozy 2br home w/ parking in downtown Annapolis, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Beautiful 2-bedroom water view house in Annapolis, 3-bedroom house in Gambrills, in the area of Annapolis, Baltimore, & DC.

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