Shady Side Holiday Rentals from NZ$355: Search Short-Term Rentals

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Our top choices for Shady Side holiday rentals

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

1. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

includes taxes & fees

1 Dec - 2 Dec

A deck with outdoor furniture, a red door, and a house with windows.

2. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

"the house was clean and fully stocked with all linens. there are some staples in the refrigerator and cabinets. All cookware and eatery are provided. there is only one grocery store in the area, so plan ahead. Fast food is not readily available. Nick responded quickly and thoroughly to all messages, that was great. It's a quiet neighborhood. It was the perfect place for a family and pet. we will return"

Jenny A.

includes taxes & fees

16 Nov - 17 Nov

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

3. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...

Amelia

includes taxes & fees

14 Nov - 15 Nov

A house with a yellow door and a window with a lamp outside.

4. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Deale

Maude H.

includes taxes & fees

15 Nov - 16 Nov

A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

5. Renovated Bungalow | Walk to Beach | Dog-Friendly

Edgewater

Diane D.

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

6. Family Home on Mayo Peninsula | Deck | Sleeps 10

Edgewater

Kristin G.

includes taxes & fees

14 Nov - 15 Nov

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

7. Relax on Kent Island in 4 Bedroom Home w/Waterview

Stevensville

Anthony P.

includes taxes & fees

15 Nov - 16 Nov

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

8. Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach

Johanna S.

includes taxes & fees

24 Nov - 25 Nov

A bedroom with a bed, a dresser, a television, and a window with curtains.

9. The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach

James L.

includes taxes & fees

19 Nov - 20 Nov

A beach with chairs and a pier in the background.

10. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

Ryan C.

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

11. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

includes taxes & fees

30 Nov - 1 Dec

A city skyline at sunset with modern buildings and a waterfront.

12. Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

Michael V.

includes taxes & fees

23 Nov - 24 Nov

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

13. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

Sarah

includes taxes & fees

16 Nov - 17 Nov

A kitchen with a wooden countertop, a stove, and a refrigerator.

14. 18th Cent. Charm in Historic Downtown Annapolis

Historic District

Bradford R.

includes taxes & fees

14 Nov - 15 Nov

A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

15. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis

William

includes taxes & fees

15 Nov - 16 Nov

A calm waterfront with boats docked, a bridge in the background, and autumn foliage along the riverbank.

16. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

West Annapolis

Jill R.

includes taxes & fees

22 Nov - 23 Nov

A calm lake with a sandy shore, surrounded by trees and houses.

17. Londontowne Home | Beach | 3BR

Edgewater

Sam A.

includes taxes & fees

15 Nov - 16 Nov

Stylish kitchen with open layout and island seating

18. Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

includes taxes & fees

14 Nov - 15 Nov

A wooden dock extending into a calm body of water with boats docked at the end.

19. Cozy 2br home w/ parking in downtown Annapolis

Historic District

Nancy N.

includes taxes & fees

16 Nov - 17 Nov

A spacious living room with a high ceiling, large windows, and a ceiling fan.

20. The Harness Creek Retreat in Annapolis

Hillsmere

Dayna A.

includes taxes & fees

15 Nov - 16 Nov

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Find holiday rentals that suit your style

Top Shady Side Hotel Reviews

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

Hyatt Place Kent Narrows & Marina

Grasonville

10/10 Excellent

Gayle

A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.

Holiday Inn Express & Suites Annapolis by IHG

Annapolis

10/10 Excellent

Mike

A spacious atrium with a high ceiling, skylights, and a patterned floor.

Graduate by Hilton Annapolis

Annapolis

10/10 Excellent

Bridget

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

The Westin Annapolis

Annapolis

10/10 Excellent

We booked this for a family Christmas, with relatives coming from Australia and Seattle joining our daughter and son-in-law and new granddaughter who live in Annapolis. The staff were friendly, efficient and obliging. We all met for dinner on Christmas night in the hotel restaurant and the set menu and service were outstanding. Breakfast next morning was also memorable. The hotel was a short 20 minute walk to downtown in the historic part of Annapolis, but a free Circulator bus was also...

Ian

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

The Inn at Perry Cabin is a beautiful, luxurious hotel in a lovely setting. Our room was elegant and comfortable we had turn down service each night with cookies and slippers left for us. The staff is helpful and friendly. There are fresh flowers and plants throughout the hotel and the grounds are beautifully landscaped. The only negative is that they charge $50 a day to use the fitness facilities! Surprising at a very expensive hotel.

2revs

Find out more about Shady Side

Everything you need to know about Shady Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shady Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shady Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shady Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shady Side. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shady Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shady Side holiday rentals we have selected for you start as low as NZ$355 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shady Side rentals

At Expedia, we put the best Shady Side holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Shady Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shady Side holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shady Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there holiday rentals in Shady Side?

Yes, there are holiday rentals close to the most popular sights in Shady Side, or you can select a more secluded option if you're looking for a relaxing stay. Shady Side is known for its shopping and restaurants. Make sure you have time to check out the parks and museums during your trip.

What are some of the best holiday rentals that Shady Side has to offer?

Lovely bay views with kayaks, bikes, fire pit, crabbing & more: This highly rated holiday home rental in Shady Side offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Shady Side?

Expedia has 12 holiday rentals for your stay in Shady Side.

What’s there to see and do in Shady Side?

Northern Chesapeake Bay and Chesapeake Bay are a couple of scenic spots to enjoy the outdoors, whereas Captain Avery Museum is one of the cultural attractions. Shadyside Park and Franklin Point State Park are other places to visit while you're in town.

What’s a holiday rental in Shady Side like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shady Side. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for family gatherings.

Shady Side Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Shady Side holiday rentals

1. Sunset Cottage - West River Access and Views!

2. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3. 3-bedroom house in Deale located on Bay many amenities and great views

4. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

5. Renovated Bungalow | Walk to Beach | Dog-Friendly

6. Family Home on Mayo Peninsula | Deck | Sleeps 10

7. Relax on Kent Island in 4 Bedroom Home w/Waterview

8. Beachside Oasis with Beach Passes & King Suite by A Haven Away

9. The Cozy Crab- Your Charming Haven in Lovely North Beach!

10. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

11. Annapolis Retreat - 7 mins from downtown Annapolis!

12. Charming Coastal/Country Home w/3 Acres & Sauna!

13. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

14. 18th Cent. Charm in Historic Downtown Annapolis

15. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

16. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

17. Londontowne Home | Beach | 3BR

18. Pool Loft Suite | Bay Access & Beach Passes

19. Cozy 2br home w/ parking in downtown Annapolis

20. The Harness Creek Retreat in Annapolis

Find holiday rentals that suit your style

Top Shady Side Hotel Reviews

Hyatt Place Kent Narrows & Marina

10/10 Excellent

Find out more about Shady Side

Shady Side holiday rentals: An excellent choice for every season

How to find incredible deals on Shady Side rentals

Frequently Asked Questions

Are there holiday rentals in Shady Side?

What are some of the best holiday rentals that Shady Side has to offer?

How many holiday rentals will I find in Shady Side?

What’s there to see and do in Shady Side?

What’s a holiday rental in Shady Side like?