Vacation rentals in Shady Side

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Top-rated vacation rentals in Shady Side

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Guest favorite

Cottage in Edgewater

4.99 out of 5 average rating, 127 reviews

Waterfront Chesapeake Bay Getaway Firepit & Pier!

Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from your private pier & enjoy the peace, serenity and bay breezes from your furnished deck and green space. Enjoy true nature and explore Selby Bay on the South River with our complimentary canoe! Super clean with water views from kitchen, dining, living room & enclosed porch! Situated in a quiet neighborhood within 45 minutes of DC & 15 minutes from Annapolis & the Naval Academy.

Jan 18 – 25

G$67,084 GYD per night

Superhost

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 14 – 21

G$66,459 GYD per night

Guest favorite

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!

Jan 11 – 18

G$85,631 GYD per night

Guest favorite

Cottage in Annapolis

4.94 out of 5 average rating, 314 reviews

Wright’s Cottage, Pets Welcome!

We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, large properties and big trees gives one a cozy, country feel, yet so close to bustling Annapolis! There is RV/EV hookup, an outdoor woodstove, and a propane grill for your use. The yard in the back of the cottage is fully fenced so your dog, cat, or maybe, pig or rabbit 🤔can freely play. Everything is very laid back at Wright’s cottage. Come stay and take the time to enjoy being you!

Oct 9 – 16

G$32,189 GYD per night

Guest favorite

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.

Dec 10 – 17

G$20,406 GYD per night

Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 156 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.

Dec 2 – 9

G$30,337 GYD per night

Guest favorite

Apartment in Crownsville

4.98 out of 5 average rating, 164 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.

Aug 13 – 20

G$24,664 GYD per night

Guest favorite

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!

Aug 5 – 12

G$37,481 GYD per night

Guest favorite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

Dec 17 – 24

G$25,361 GYD per night

Guest favorite

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.

Mar 22 – 29

G$45,209 GYD per night

Guest favorite

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.

Apr 13 – 20

G$83,334 GYD per night

Guest favorite

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.

Jul 30 – Aug 6

G$20,801 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Shady Side vacation rentals

Kitchen

Wifi

Pool

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

Guest favorite

Apartment in Edgewater

4.92 out of 5 average rating, 399 reviews

Pet Friendly Garden Apartment Near Annapolis

Sep 23 – 30

G$23,246 GYD per night

Guest favorite

Cottage in North Beach

4.96 out of 5 average rating, 273 reviews

Waterfront Cottage Near Herrington and North Beach

Jul 26 – Aug 2

G$51,868 GYD per night

Guest favorite

Home in Shady Side

4.97 out of 5 average rating, 65 reviews

Canary Pointe-A popular getaway for 2!

Dec 13 – 20

G$35,259 GYD per night

Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 18 reviews

The Cottage

Dec 27 – Jan 3

G$46,933 GYD per night

Guest favorite

Cottage in Shady Side

5.0 out of 5 average rating, 9 reviews

Tranquil Waterfront Cottage - 50 minutes to DC

Jul 27 – Aug 3

G$74,151 GYD per night

Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 10 reviews

Waterfront Community by Bay | Sleeps 6 | Game Room

Jun 1 – 8

G$45,803 GYD per night

Guest favorite

Home in Shady Side

4.98 out of 5 average rating, 42 reviews

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

May 13 – 20

G$80,128 GYD per night

Guest favorite

Home in Edgewater

4.95 out of 5 average rating, 38 reviews

Relaxing Turkey Point Retreat-Steps to the marina!

Feb 22 – Mar 1

G$31,883 GYD per night

Show all

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
G$18,764 GYD 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.

Vacation rentals in Shady Side

Top-rated vacation rentals in Shady Side

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Shady Side vacation rentals

Stay near Shady Side's top sights

Other great vacation rentals in Shady Side

Apartment in Edgewater

Cottage in North Beach

Home in Shady Side

Home in Shady Side

Cottage in Shady Side

Home in Shady Side

Home in Shady Side

Home in Edgewater

Quick stats about vacation rentals in Shady Side

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

How much does it cost to stay in house rentals in Shady Side?

Are there pet-friendly vacation rentals in Shady Side?

What are the most popular amenities for House Rentals in Shady Side?

Do house rentals in Shady Side have a kitchen?

Do house rentals in Shady Side have wifi?

Are there vacation rentals with a dedicated workspace in Shady Side?

Do house rentals in Shady Side have free parking?

Do house rentals in Shady Side have air conditioning?

Destinations to explore