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House vacation rentals in Shady Side

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Top-rated house rentals in Shady Side

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Home in Shady Side

4.88 out of 5 average rating, 174 reviews

Cattail Landing- Photographer's Waterfront Retreat

"Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take a kayak out after breakfast to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acre in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home (w. 1GB hi-speed internet).

Jan 8 – 15

R5,997 ZAR per night

Home in Shady Side

5.0 out of 5 average rating, 117 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

Feb 12 – 19

R8,339 ZAR per night

Home in North Beach

4.84 out of 5 average rating, 178 reviews

Warm Home Overlooking the Chesapeake Bay

Sitting on the Chesapeake Bay, North Beach is a town where you are so close to things, yet can feel so far away. Only 45 minutes form Washington, DC, you can sit on one of three decks and gaze into the Chesapeake Bay, enjoying all that small town life has to offer. An open plan, with defined spaces, the house is at once cozy (with a fireplace) and spacious for a family. It is great for couples, adventurers, business travelers, and families. This is not a house for large groups or parties.

Sep 4 – 11

R5,146 ZAR per night

Home in Stevensville

5.0 out of 5 average rating, 101 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can imagine. Travel just 4 short miles from the Bay Bridge to this 2 story home overlooking the Chesapeake Bay. Sunsets galore and constantly changing views of Ships, Sailboats, Osprey, Eagles, Heron and much more. Calm water and strong winds are all beautiful to watch from our two levels. 12' x 52' covered patio on main level and 12' x 52' three season room on the upper level.

Apr 3 – 10

R17,985 ZAR per night

Home in Glen Burnie

4.97 out of 5 average rating, 397 reviews

Secluded acre near BWI and Baltimore

Secluded suburban acre 8 minutes from BWI Airport, 15 minutes from Baltimore's Inner Harbor and from Fort Meade, and 45 minutes from Washington DC. Private house attached to host house has 1220 square feet of cozy comfort--4 times the size of a hotel room! House includes 2 bedrooms (one queen, one double), 1.5 baths, living room, foyer, dining room, full kitchen, and washer/dryer. The one-acre lot has hundreds of trees and is great for pets. Level 2 charging station is good for all EVs.

Sep 27 – Oct 4

R2,336 ZAR per night

Home in Edgewater

4.98 out of 5 average rating, 100 reviews

Luxury Modern Home on Water+Hotub- Annapolis 25min

Retreat with family, friends or team members to an idyllic waterfront setting. Our "Flight Deck" is the perfect gathering space. Enjoy the breathtaking and peaceful grounds while taking advantage of the well-appointed living/gathering spaces. This mid-century house (approx 2800 SF) sits on a 3/4 acre property - perfect for lawn games and zip lining. From a 20x20 furnished deck, fire pit and hot tub enjoy breathtaking views. Mayo Beach and Beverly Triton Nature Park are 1 mile away.

Jun 17 – 24

R17,487 ZAR per night

Home in Annapolis

4.99 out of 5 average rating, 198 reviews

Cape St Claire waterfront getaway

This is a private over the garage apartment located in Cape St Claire, about 5 miles from downtown Annapolis, 2 miles to the Bay Bridge. Private entrance, on site parking, 1- 2 guests. We encourage our guests to enjoy the large back yard patio with magnificent views of the Magothy River and Chesapeake Bay ! Approximately 30 miles to Washington, and Baltimore. 30 minutes to BWI airport. TV and internet. A community beaches just a short walk away. ADULTS ONLY, NO SMOKING, NO PETS.

Nov 13 – 20

R2,705 ZAR per night

Home in Chesapeake Beach

4.91 out of 5 average rating, 111 reviews

Indoor pool/spa nestled in Southern Md. woods.

Contemporary all-brick French manor nestled within 16-acres of secluded woodlands. Indoor pool/spa with waterfall inside a stunning, sunlit atrium. Three bedrooms and three bathrooms accommodate 6-8 people. Centrally located near the Chesapeake Bay where quaint towns include restaurants, antiques, sandy beaches and fishing boat rentals. Centrally located for trips in all directions: Washington, D.C. (35 miles); Annapolis (30 miles) Baltimore (50 miles) and Ocean City (139 miles).

Jul 7 – 14

R14,893 ZAR per night

Home in Deale

4.98 out of 5 average rating, 113 reviews

Chesapeake Waterfront-Hot Tub-Kayaks-King Bed

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Bring your own boat! Make wonderful memories. Great place for families and multi family groups.

Dec 11 – 18

R10,258 ZAR per night

Home in Deale

4.99 out of 5 average rating, 125 reviews

Hannah’s Hideaway

Cottage style with water view of Rockhold Creek. Water taxi right out front of house to take you to local restaurants. Crabbing excursions or fishing charters available for extra cost. Dog friendly. Local restaurants all within 1 mile from location. Fenced in back yard. Picnic table and fire pit to have own personal crab feasts or cookout. Many local restaurants with outside musicians.Grocery store and gas/liquor stores within 5 minutes from house.

Dec 16 – 23

R4,409 ZAR per night

Home in Cambridge

4.92 out of 5 average rating, 180 reviews

Guest House: Farm homestead

Quiet country guest house with 1 BR/ 1 BA, queen sleeper sofa and fully stocked kitchen. Coffee/creamer/sugar provided. Come relax & enjoy the row boat and paddle boat, fishing in the ponds (C&R, No Pond Access from August 24 thru January 30 annually), grill on the deck, watch the bikers roll by (Ironman course) or finish your day by the fire-pit with s'mores! All this and only 3 miles to town and on the Eagle Man and Iron Man race course.

Aug 25 – Sep 1

R2,344 ZAR per night

Home in Tracys Landing

4.99 out of 5 average rating, 166 reviews

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower.

Nov 30 – Dec 7

R8,644 ZAR per night

Vacation rentals for every style

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Hotels

Stylish accommodations and amenities

Unique stays

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Homes

Comfortable places with all the essentials

Popular amenities for Shady Side house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Kent Narrows

5.0 out of 5 average rating, 278 reviews

Chester Riverfront At Kent Narrows

Oct 19 – 26

R6,875 ZAR per night

Home in Saint Michaels

4.97 out of 5 average rating, 238 reviews

Miles Aweigh

Apr 4 – 11

R9,510 ZAR per night

Home in Queenstown

4.81 out of 5 average rating, 143 reviews

Bay Breeze Retreat

Nov 15 – 22

R17,050 ZAR per night

Home in Severn

4.81 out of 5 average rating, 102 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

Mar 28 – Apr 4

R11,257 ZAR per night

Home in Edgewater

4.97 out of 5 average rating, 30 reviews

Entire Beach House with Pool and Hot Tub

Oct 31 – Nov 7

R6,095 ZAR per night

Home in Annapolis

4.95 out of 5 average rating, 41 reviews

Naptown Suite

Jan 3 – 10

R2,149 ZAR per night

Home in Deale

5.0 out of 5 average rating, 10 reviews

Modern Bay Dream

Dec 2 – 9

R9,096 ZAR per night

Home in Edgewater

4.97 out of 5 average rating, 30 reviews

Waterfront | Pool | Hot tub | Beach Access

Oct 3 – 10

R12,185 ZAR per night

Weekly house rentals

Home in Shady Side

4.97 out of 5 average rating, 65 reviews

Canary Pointe-A popular getaway for 2!

Jul 8 – 15

R3,275 ZAR per night

Home in Shady Side

5.0 out of 5 average rating, 18 reviews

The Cottage

Jan 6 – 13

R4,235 ZAR per night

Home in Shady Side

5.0 out of 5 average rating, 10 reviews

Waterfront Community by Bay | Sleeps 6 | Game Room

May 11 – 18

R4,034 ZAR per night

Home in Edgewater

4.95 out of 5 average rating, 38 reviews

Relaxing Turkey Point Retreat-Steps to the marina!

Feb 5 – 12

R2,398 ZAR per night

Home in Shady Side

4.88 out of 5 average rating, 24 reviews

Cozy Bay home w/180 degree view

Jun 25 – Jul 2

R4,906 ZAR per night

Home in Shady Side

4.96 out of 5 average rating, 89 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

Aug 19 – 26

R5,895 ZAR per night

Home in Shady Side

4.98 out of 5 average rating, 42 reviews

"Pier Joy!" - 3BR Waterfront Home W/Private Dock

Jun 24 – Jul 1

R8,309 ZAR per night

Home in Shady Side

4.96 out of 5 average rating, 54 reviews

Waterfront Sanctuary only 50 Min. From DC/Balt.

Sep 30 – Oct 7

R12,117 ZAR per night

Private house rentals

Home in North Beach

5.0 out of 5 average rating, 95 reviews

Waterfront Home w/ Hot Tub, Pets ok, Peleton

Nov 30 – Dec 7

R9,717 ZAR per night

Home in Harwood

4.96 out of 5 average rating, 27 reviews

Quiet Farm Stay near Annapolis

Sep 4 – 11

R3,861 ZAR per night

Home in Edgewater

4.95 out of 5 average rating, 99 reviews

Annapolis Area Waterside Retreat

Jan 30 – Feb 6

R8,639 ZAR per night

Home in Deale

4.95 out of 5 average rating, 21 reviews

Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt

Sep 14 – 21

R17,157 ZAR per night

Home in Deale

5.0 out of 5 average rating, 8 reviews

Quiet Getaway in Waterfront Community

Jul 18 – 25

R6,068 ZAR per night

Home in North Beach

4.97 out of 5 average rating, 60 reviews

Charming Herrington / Rose Haven Cottage

Sep 29 – Oct 6

R3,426 ZAR per night

Home in North Beach

4.98 out of 5 average rating, 95 reviews

Huge Beach Bungalow- Yard, Beach Pass, King Beds

Jan 28 – Feb 4

R6,810 ZAR per night

Home in North Beach

4.98 out of 5 average rating, 47 reviews

Cheerful Two Bedroom Home on the Chesapeake Bay!

Apr 6 – 13

R4,844 ZAR per night

Quick stats about house rentals in Shady Side

Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
810 reviews
Nightly prices starting at
R1,693 ZAR before taxes and fees

Destinations to explore