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Vacation rentals with outdoor seating in Shady Side

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Shady Side

Guests agree: these outdoor seating rentals 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).

Jan 8 – 15

R6,126 ZAR per night

Cottage in Edgewater

4.99 out of 5 average rating, 129 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.

Aug 27 – Sep 3

R6,452 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

R8,519 ZAR per night

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!

Aug 14 – 21

R3,283 ZAR per night

Guesthouse in Annapolis

4.9 out of 5 average rating, 207 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 13 – 20

R1,882 ZAR per night

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.

Nov 16 – 23

R2,692 ZAR per night

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 29 – Sep 5

R3,453 ZAR per night

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.

Apr 24 – May 1

R4,164 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

R4,502 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

R8,825 ZAR per night

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.

Oct 10 – 17

R8,296 ZAR per night

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.

Aug 23 – 30

R2,334 ZAR per night

Vacation rentals for every style

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Popular amenities for Shady Side outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Home in Deale

4.98 out of 5 average rating, 113 reviews

Chesapeake Waterfront-Hot Tub-Kayaks-King Bed

Dec 11 – 18

R10,476 ZAR per night

Home in Edgewater

4.98 out of 5 average rating, 100 reviews

Luxury Modern Home on Water+Hotub- Annapolis 25min

Jun 17 – 24

R17,858 ZAR per night

Home in Annapolis

4.99 out of 5 average rating, 198 reviews

Cape St Claire waterfront getaway

Nov 13 – 20

R2,759 ZAR per night

Home in Edgewater

4.95 out of 5 average rating, 119 reviews

House in Edgewater Maryland

Nov 28 – Dec 5

R7,184 ZAR per night

Home in Cambridge

4.92 out of 5 average rating, 180 reviews

Guest House: Farm homestead

Aug 25 – Sep 1

R2,393 ZAR per night

Home in Silver Spring

4.99 out of 5 average rating, 150 reviews

Entire Guest Suite/Apt in Silver Spring/FDA

Nov 19 – 26

R1,905 ZAR per night

Home in Stevensville

5.0 out of 5 average rating, 101 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Apr 3 – 10

R18,361 ZAR per night

Home in Glen Burnie

4.97 out of 5 average rating, 397 reviews

Secluded acre near BWI and Baltimore

Sep 27 – Oct 4

R2,385 ZAR per night

Apartment rentals with outdoor seating

Apartment in Stevensville

4.98 out of 5 average rating, 240 reviews

Boutique by the Bay

Mar 15 – 22

R3,603 ZAR per night

Apartment in Crownsville

4.98 out of 5 average rating, 164 reviews

“River Sweet" Private Apartment

Jun 28 – Jul 5

R2,421 ZAR per night

Apartment in Bowie

4.98 out of 5 average rating, 117 reviews

Couple's Retreat - Private Entrance Basement Apt

Jul 9 – 16

R2,253 ZAR per night

Apartment in Chester

4.97 out of 5 average rating, 234 reviews

Cozy Waterfront Apartment Chester, MD

Feb 15 – 22

R2,434 ZAR per night

Apartment in Annapolis

4.91 out of 5 average rating, 122 reviews

Chesapeake Bird Nest

Sep 24 – Oct 1

R2,734 ZAR per night

Apartment in Silver Spring

4.95 out of 5 average rating, 133 reviews

New - Super Host/Silver Spring/Full Kitchen-Cute

Apr 15 – 22

R1,839 ZAR per night

Apartment in Silver Spring

4.93 out of 5 average rating, 395 reviews

Escape to a Sunny Apartment in a Quiet D.C. Suburb

Oct 15 – 22

R1,802 ZAR per night

Apartment in Washington

4.93 out of 5 average rating, 169 reviews

Capitol Hill Charm ~ Modern Refinement

Oct 2 – 9

R2,219 ZAR per night

Condo rentals with outdoor seating

Condo in Annapolis

4.99 out of 5 average rating, 126 reviews

New Downtown Annapolis Condo With Free Parking

Nov 21 – 28

R4,371 ZAR per night

Condo in Oxford

4.98 out of 5 average rating, 112 reviews

Cozy Oxford Getaway

Dec 22 – 29

R3,828 ZAR per night

Condo in Washington

4.93 out of 5 average rating, 140 reviews

Unique, charming garden apartment

Feb 3 – 10

R1,814 ZAR per night

Condo in Fort Washington

4.84 out of 5 average rating, 188 reviews

The Get-Away at National Harbor

May 31 – Jun 7

R3,317 ZAR per night

Condo in Washington

4.9 out of 5 average rating, 448 reviews

Gorgeous, large, modern 1 BR on Hist. Logan Circle

Sep 6 – 13

R3,158 ZAR per night

Condo in Washington

4.99 out of 5 average rating, 208 reviews

Hill East BnB - Modern Style and Comfort 3BR/3BA

Jan 9 – 16

R6,764 ZAR per night

Condo in Washington

4.92 out of 5 average rating, 133 reviews

Sunny, New 2BR w/ 65" TV, Firepit, Patio & Parking

Jul 16 – 23

R3,195 ZAR per night

Condo in Washington

4.97 out of 5 average rating, 166 reviews

Heart of DC! Modern Upscale Comfy 2BR/2BA in Shaw

May 29 – Jun 5

R4,367 ZAR per night

Quick stats about vacation rentals with outdoor seating 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
910 reviews
Nightly prices starting at
R1,693 ZAR before taxes and fees

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