Holiday rentals with a patio in Shady Side

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Top-rated Holiday Accommodation with Outdoor Verandahs in Shady Side

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Guest favourite

Cottage in North Beach

4.95 out of 5 average rating, 77 reviews

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

8–15 Aug

$349 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

$904 NZD per night

Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 10 reviews

Waterfront Community by Bay | Sleeps 6 | Game Room

Amazing & spacious private house with 3 bedroom, 2 bathroom, Game Room, eat-in Kitchen, outdoor deck & grill, and a Herb Garden. Just a block away from a great Scenic view of the Chesapeake Bay. Beautiful sunrises and sunsets. Quite and friendly neighborhood that is great for walking, jogging, or biking. Community private little beach with a great fishing pier, a playground, picnic areas, a field, and a Bay-Front Park! Close to Annapolis, DMV, Six Flags, Baltimore, shopping, and restaurants.

11–18 May

$445 NZD per night

Guest favourite

Home in Annapolis

4.95 out of 5 average rating, 41 reviews

Naptown Suite

Welcome to the Naptown Suite! This stylish space offers guests a one-bedroom and full bath apartment with a kitchenette and private entrance. Located just 3.1 miles from the Naval Academy, this basement suite is nestled in a safe and family friendly neighborhood that boasts a lovely beach, kayak launches, and walking access to Quiet Waters Park. After a day of hiking, biking, or exploring local breweries and wineries, return home to chill by the firepit. Come see all Annapolis has to offer!

3–10 Jan

$235 NZD per night

Guest favourite

Home in Stevensville

4.95 out of 5 average rating, 151 reviews

Relax on Kent Island in 3 Bedroom Home w/Waterview

Enjoy your vacation in this Beautiful & Stylish 3 Bedroom Home with a view of the Chesapeake Bay from living room & kitchen! Perfect for Families & sleeps 11. We are conveniently located to many areas/cities: Annapolis- 20 miles Baltimore- 45 Wash. DC- 50 Easton- 35 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions. This is a Non-Smoking House. Also No Pets, Parties or Large Groups (11 max.). Book Today!

7–14 Aug

$725 NZD per night

Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 17 reviews

Peaceful Waterfront Getaway

Welcome to our waterfront oasis on Parish’s Creek just off of the Chesapeake Bay! Our spacious house is the perfect retreat for fishing enthusiasts, nature lovers, and those seeking a serene getaway. With a private pier, kayaks, and easy access to nearby attractions, our home is an ideal destination for your next vacation. Located less than an hour away from Washington, D.C. and 20 minutes from Annapolis, our quiet house provides a convenient escape from the hustle and bustle of city life.

9–16 Sep

$1,894 NZD per night

Guest favourite

Guest suite in North Beach

4.96 out of 5 average rating, 27 reviews

Brand New Guest Suite - Cozy 1 Bedroom Bungalow

New construction built as an addition; a one bedroom guest suite with a mini bar, a full bathroom and a private separate entrance. Your guest suite was built as a new addition to the classic 1940's bungalows that define North Beach. Tastefully furnished with various artwork displayed throughout the unit. The guest suite is located in North Beach, MD, only several mins walking distance to all the restaurants, shops and boardwalk pier, beach & Chesapeake Bay.

17–24 Oct

$230 NZD per night

Guest favourite

Cottage in Shady Side

5.0 out of 5 average rating, 9 reviews

Tranquil Waterfront Cottage - 50 minutes to DC

Escape to our peaceful, riverside cottage. Enjoy sweeping views of the West River with 390 feet of private waterfront. Spectacular sunsets, blue heron and birds galore. Cottage is recently-renovated and tastefully appointed with a kitchen set for the cooking enthusiast. Expansive yard with over 2 acres - it is unusual to have this much distance from neighbors in Shady Side - and plenty of space to relax shaded by old oaks. Under an hour from DC.

10–17 Aug

$716 NZD per night

Guest favourite

Home in Shady Side

4.96 out of 5 average rating, 54 reviews

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

30 Sep – 7 Oct

$1,283 NZD per night

Guest favourite

Guesthouse in Glen Burnie

4.94 out of 5 average rating, 263 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

25 Dec – 1 Jan

$455 NZD per night

Guest favourite

Guest suite in Arnold

4.97 out of 5 average rating, 129 reviews

Pet Friendly Captains Quarters, Near Annapolis, EV

Yes, the hot tub IS open! 24/7/365 :-) This space has been fully updated with all the conveniences and amenities to make your stay enjoyable! We offer: - a king bed so you get a stellar night's sleep, - a queen bed sleeper sofa for family travels, - high speed internet, - a furnished kitchen, - private en-suite bathroom, and - a coffee bar. We're close to everything - located four miles from my hometown Annapolis!

15–22 Sep

$386 NZD per night

Guest favourite

Guest suite in Chesapeake Beach

4.95 out of 5 average rating, 82 reviews

Nice Guest Suite at Chesapeake Bay

Take it easy at this unique and tranquil getaway. Come and relax in our modern & comfortable guest suite to enjoy a small-town quiet setting with amazing Chesapeake Bay views. A short drive from Washington DC (45 min), Annapolis (30 Min), or Baltimore (1 hr). Groceries, boardwalks, restaurants are all within walking distance. Enjoy cable TV, high-speed Internet, and strong wifi through Xfinity.

29 Mar – 5 Apr

$261 NZD per night