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Vacation rentals in Shady Side

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Top-rated vacation rentals in Shady Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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).

Home in Shady Side

5.0 out of 5 average rating, 116 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!

Apartment in North Beach

4.97 out of 5 average rating, 102 reviews

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

Guesthouse in Annapolis

4.9 out of 5 average rating, 206 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Guesthouse in Annapolis

4.97 out of 5 average rating, 155 reviews

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

Apartment in Crownsville

4.98 out of 5 average rating, 163 reviews

“River Sweet" Private Apartment

River Sweet has everything you need for a fun and relaxing getaway. Cozy and clean, River Sweet provides all the comforts of home, including your own driveway and entrance. You'll delight in privacy while enjoying a safe, waterfront neighborhood. A local mini mart and restaurant are close by. And, you are centrally located between Annapolis, Baltimore and Washington for fun excursions! Please let us know if you need a long-term stay. We would be happy to accommodate you.

Guesthouse in Galesville

4.95 out of 5 average rating, 163 reviews

Gorgeous water view studio!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

Apartment in Deale

4.91 out of 5 average rating, 614 reviews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Guesthouse in Annapolis

4.99 out of 5 average rating, 106 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Guest suite in Edgewater

4.89 out of 5 average rating, 437 reviews

South River Park Apartment

Located minutes from Annapolis, MD the in-law apartment offers access to Baltimore and DC in under an hour. The apartment offers its own entrance, full kitchen, one bathroom, one bedroom, tile floors, pullout sofa, Wifi, and parking. The apartment is registered with the Anne Arundel County Dept. of Inspections & Permits, #STR-15, for short term rentals.

Cottage in North Beach

4.96 out of 5 average rating, 273 reviews

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

Guesthouse in Annapolis

4.97 out of 5 average rating, 197 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Recently renovated (Feb. 2021) one bedroom Guesthouse with fully equipped kitchen, new king sized bed with premium Saatva mattress, full bathroom and large living room in a quiet neighborhood near the South River, Quiet Waters Park and downtown historic Annapolis. We employ professional cleaning services between each guest stay.

Vacation rentals for every style

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Popular amenities for Shady Side vacation rentals

Free parking on premises

Air conditioning

Stay near Shady Side's top sights

Pirates Cove Restaurant and Dock Bar44 locals recommend

Stan and Joes Riverside20 locals recommend

Christopher's Fine Foods30 locals recommend

JesseJay's Latin Inspired Kitchen16 locals recommend

Drift Wood Diner8 locals recommend

West River pit bbq4 locals recommend

Other great vacation rentals in Shady Side

Cottage in Edgewater

4.99 out of 5 average rating, 126 reviews

Waterfront Chesapeake Bay Getaway Firepit & Pier!

Cottage in Annapolis

4.94 out of 5 average rating, 314 reviews

Wright’s Cottage, Pets Welcome!

Home in Shady Side

4.97 out of 5 average rating, 65 reviews

Canary Pointe-A popular getaway for 2!

Home in Shady Side

5.0 out of 5 average rating, 17 reviews

The Cottage

Home in Shady Side

5.0 out of 5 average rating, 10 reviews

Waterfront Community by Bay | Sleeps 6 | Game Room

Home in Shady Side

4.91 out of 5 average rating, 23 reviews

Baydream Believer -Chesapeake Bay water community

Cottage in Shady Side

5.0 out of 5 average rating, 9 reviews

Tranquil Waterfront Cottage - 50 minutes to DC

Home in Shady Side

4.96 out of 5 average rating, 54 reviews

Waterfront Sanctuary only 50 Min. From DC/Balt.

Quick stats about vacation rentals in Shady Side

Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1K reviews
Nightly prices starting at
$90 before taxes and fees

Frequently Asked Questions

How much does it cost to stay in house rentals in Shady Side?
Experience the best of Shady Side with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Shady Side?
Four-legged friends are welcome in Shady Side. Choose from more than 10 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Shady Side?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with free parking, over 20 homes with a kitchen, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Shady Side have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Shady Side. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shady Side have wifi?
Absolutely! We offer over 20 house rentals with wifi in Shady Side. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Shady Side?
Yes! Work meets play with ease at over 20 vacation rentals in Shady Side featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Shady Side have free parking?
Absolutely! We offer over 20 house rentals with free parking in Shady Side. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shady Side have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Shady Side. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore