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Holiday rentals with outdoor seating in Shady Side

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Shady Side

Guests agree: These Holiday Houses with Outdoor Seating 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).

8–15 Jan

$656 NZD per night

Guest favourite

Cottage in Edgewater

4.99 out of 5 average rating, 128 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.

27 Aug – 3 Sep

$680 NZD per night

Guest favourite

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!

12–19 Feb

$914 NZD per night

Guest favourite

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!

14–21 Aug

$360 NZD per night

Guest favourite

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.

13–20 Dec

$205 NZD per night

Guest favourite

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.

16–23 Nov

$281 NZD per night

Guest favourite

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!

29 Aug – 5 Sep

$359 NZD per night

Guest favourite

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.

24 Apr – 1 May

$429 NZD per night

Guest favourite

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.

16–23 Dec

$472 NZD per night

Guest favourite

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.

30 Nov – 7 Dec

$917 NZD per night

Guest favourite

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.

10–17 Oct

$829 NZD per night

Guest favourite

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.

23–30 Aug

$239 NZD per night

Holiday rentals for every style

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Popular amenities for Shady Side outdoor seating rentals

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

Guest favourite

Home in Deale

4.98 out of 5 average rating, 113 reviews

Chesapeake Waterfront-Hot Tub-Kayaks-King Bed

11–18 Dec

$1,108 NZD per night

Guest favourite

Home in Edgewater

4.98 out of 5 average rating, 100 reviews

Luxury Modern Home on Water+Hotub- Annapolis 25min

17–24 Jun

$1,882 NZD per night

Guest favourite

Home in Annapolis

4.99 out of 5 average rating, 198 reviews

Cape St Claire waterfront getaway

13–20 Nov

$274 NZD per night

Guest favourite

Home in Edgewater

4.95 out of 5 average rating, 119 reviews

House in Edgewater Maryland

28 Nov – 5 Dec

$747 NZD per night

Guest favourite

Home in Cambridge

4.92 out of 5 average rating, 179 reviews

Guest House: Farm homestead

25 Aug – 1 Sep

$231 NZD per night

Guest favourite

Home in Silver Spring

4.99 out of 5 average rating, 150 reviews

Entire Guest Suite/Apt in Silver Spring/FDA

19–26 Nov

$210 NZD per night

Guest favourite

Home in Stevensville

5.0 out of 5 average rating, 101 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

3–10 Apr

$1,787 NZD per night

Guest favourite

Home in Glen Burnie

4.97 out of 5 average rating, 396 reviews

Secluded acre near BWI and Baltimore

27 Sep – 4 Oct

$249 NZD per night

Apartment rentals with outdoor seating

Guest favourite

Apartment in Stevensville

4.98 out of 5 average rating, 240 reviews

Boutique by the Bay

15–22 Mar

$351 NZD per night

Guest favourite

Apartment in Crownsville

4.98 out of 5 average rating, 164 reviews

“River Sweet" Private Apartment

28 Jun – 5 Jul

$251 NZD per night

Guest favourite

Apartment in Bowie

4.98 out of 5 average rating, 117 reviews

Couple's Retreat - Private Entrance Basement Apt

9–16 Jul

$237 NZD per night

Guest favourite

Apartment in Chester

4.97 out of 5 average rating, 234 reviews

Cozy Waterfront Apartment Chester, MD

15–22 Feb

$246 NZD per night

Guest favourite

Apartment in Annapolis

4.91 out of 5 average rating, 122 reviews

Chesapeake Bird Nest

24 Sep – 1 Oct

$286 NZD per night

Guest favourite

Apartment in Silver Spring

4.95 out of 5 average rating, 133 reviews

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

15–22 Apr

$183 NZD per night

Guest favourite

Apartment in Silver Spring

4.93 out of 5 average rating, 395 reviews

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

15–22 Oct

$189 NZD per night

Guest favourite

Apartment in Washington

4.93 out of 5 average rating, 169 reviews

Capitol Hill Charm ~ Modern Refinement

2–9 Oct

$250 NZD per night

Condo rentals with outdoor seating

Guest favourite

Condo in Annapolis

4.99 out of 5 average rating, 126 reviews

New Downtown Annapolis Condo With Free Parking

21–28 Nov

$471 NZD per night

Guest favourite

Condo in Oxford

4.98 out of 5 average rating, 112 reviews

Cozy Oxford Getaway

22–29 Dec

$369 NZD per night

Guest favourite

Condo in Washington

4.93 out of 5 average rating, 140 reviews

Unique, charming garden apartment

3–10 Feb

$204 NZD per night

Guest favourite

Condo in Fort Washington

4.84 out of 5 average rating, 188 reviews

The Get-Away at National Harbor

31 May – 7 Jun

$347 NZD per night

Guest favourite

Condo in Washington

4.9 out of 5 average rating, 448 reviews

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

6–13 Sep

$348 NZD per night

Guest favourite

Condo in Washington

4.99 out of 5 average rating, 208 reviews

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

9–16 Jan

$741 NZD per night

Guest favourite

Condo in Washington

4.92 out of 5 average rating, 133 reviews

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

16–23 Jul

$349 NZD per night

Guest favourite

Condo in Washington

4.97 out of 5 average rating, 166 reviews

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

29 May – 5 Jun

$488 NZD per night

Quick stats about holiday 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
$152 NZD before taxes and fees

Destinations to explore