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, 130 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.

Mar 12 – 19

G$67,079 GYD per night

Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 119 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 21 – 28

G$90,795 GYD per night

Guest favorite

Home in Edgewater

4.95 out of 5 average rating, 101 reviews

Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

Feb 19 – 26

G$95,735 GYD per night

Guest favorite

Apartment in North Beach

4.96 out of 5 average rating, 104 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.

Apr 22 – 29

G$27,582 GYD per night

Guest favorite

Cottage in Annapolis

4.94 out of 5 average rating, 315 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!

Aug 15 – 22

G$34,244 GYD per night

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 209 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 15 – 22

G$20,405 GYD per night

Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 157 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.

Oct 21 – 28

G$29,493 GYD per night

Guest favorite

Guesthouse in Galesville

4.95 out of 5 average rating, 164 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!

Sep 29 – Oct 6

G$37,479 GYD per night

Guest favorite

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.

May 23 – 30

G$102,326 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.

Feb 12 – 19

G$45,207 GYD per night

Guest favorite

Guesthouse in Annapolis

4.99 out of 5 average rating, 108 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.

Jul 16 – 23

G$83,329 GYD per night

Guest favorite

Guest suite in Edgewater

4.89 out of 5 average rating, 441 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.

Dec 2 – 9

G$20,799 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

Home in Shady Side

4.97 out of 5 average rating, 67 reviews

Canary Pointe-A popular getaway for 2!

Jan 31 – Feb 7

G$32,351 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$46,930 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 26 – Aug 2

G$74,146 GYD per night

Guest favorite

Cottage in Shady Side

4.9 out of 5 average rating, 29 reviews

Luxe Chesapeake Cabin * River View* Fire Pit*

Feb 15 – 22

G$50,641 GYD per night

Guest favorite

Home in Shady Side

4.92 out of 5 average rating, 24 reviews

Baydream Believer -Chesapeake Bay water community

Nov 24 – Dec 1

G$89,857 GYD per night

Guest favorite

Home in Shady Side

4.96 out of 5 average rating, 90 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

Sep 15 – 22

G$72,142 GYD per night

Guest favorite

Home in Shady Side

4.96 out of 5 average rating, 55 reviews

Waterfront Sanctuary only 50 Min. From DC/Balt.

Jan 12 – 19

G$134,276 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

Sep 22 – 29

G$100,953 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$18,762 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 a kitchen, over 20 homes with free parking, over 20 homes with air conditioning, over 20 homes with wifi, 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

Home in Shady Side

Home in Shady Side

Cottage in Shady Side

Cottage in Shady Side

Home in Shady Side

Home in Shady Side

Home in Shady Side

Home in Shady Side

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