Bespoke Usa Travel - Vacation Rentals in Shady Side

New Waterfront Home near Annapolis, MD From US $1,901
         

10.0 (33 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Grandma's Summer House Beverly Beach From US $178
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Chesapeake Paradise LITE 4+br3ba Peaceful Watrfrnt From US $425
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Home w/Beach Access Boat Slip Basketball Court From US $740
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Waterfront Sanctuary only 50 Min. From DC/Balt. From US $683
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
Sunrise Suite Exquisite Bay View Lux/Rom/Spiritual From US $232
         

Luxury Places to Stay in Shady Side

Over 43+ Luxury Places to Stay in or Near Shady Side
Holiday Promo: Get 10% Off Holiday Stays From US $843
         

9.8 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Zen Sunset Retreat on Waterfront at West River, MD From US $831
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Waterfront Home on the Chesapeake Bay! From US $571
         

9.8 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt From US $540
         

9.4 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Enchanting West River Retreat From US $527
         

10.0 (9 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Shady Side

Over 3+ Top-Rated Vacation Rentals with a Pool in or Near Shady Side
Adorable waterside cottage with pool Beach community From US $522
         

9.2 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Shady Side

Over 15+ Pet-Friendly Vacation Rentals in or Near Shady Side
Grandma’s Summer House @ Beverly Beach From US $395
         

9.8 (7 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Bay views with kayaks, bikes, fire pit, crabbing and more From US $247
         

9.6 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Chesapeake Bayside Loft From US $165
         

8.0 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
5-years young STUNNING home with water view! From US $418
         

10.0 (17 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
"PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK From US $340
         

9.8 (37 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pier Relaxation! @ the Chesapeake Bay! From US $323
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Riverside Retreat - Views Galore. Near DC/Baltimore and Annapolis, MD From US $500
         

*Chesapeake Bayside Bungalow* From US $362
         

8.6 (37 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Shady Side

Over 6+ Large Vacation Homes & Villas in or Near Shady Side
Franklin At The Bay. Opening Dec 5!
New
From US $363
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Chesapeake Cabin From US $405
         

5.0 (1 Review)
Cabin
  • Child Friendly
Luxe Chesapeake Cabin House near Lake From US $355
         

New
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
River Cottage with Beach and Dock From US $465
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Expansive Beverly Triton Retreat From US $392
         

New
House
  • Air Conditioner
  • Pet Friendly
  • TV

Shady Side Varoom and Airbnb Places to Stay Under $200

Over 3+ Shady Side Varoom and Airbnb Places to Stay Under $200
Chesapeake Sparkles Sky-Lit Studio Flat + Solarium From US $178
         

9.8 (21 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Chesapeake Bayside Loft
New
From US $161
         

New
House
  • Air Conditioner
  • Security/Safety
  • Child Friendly

Instantly Bookable Vacation Homes in Shady Side

Over 10+ Instantly Bookable Vacation Homes in or Near Shady Side
Calloway Drive Retreat | House in Shady Side From US $222
         

Water views from every window of unique round house From US $767
         

Waterfront Shady Side Home w/Chesapeake Bay View! From US $256
         

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis! From US $387
         

Round House -- Panoramic Views -- Chesapeake Bay From US $358
         

4.9 (16 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Bedding/Linens
Chesapeake Bayside Bungalow
New
From US $236
         

2.0 (1 Review)
House
  • Air Conditioner
  • TV
  • Security/Safety

About Shady Side Vacation Rentals

With more than 52 Shady Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bespokeusatravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Shady Side.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bespokeusatravel Shady Side, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Shady Side. Places to stay near Shady Side are 1313.41 ft² on average, with prices averaging $508 a night.

Bespokeusatravel makes it easy and safe to find and compare vacation rentals in Shady Side with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Shady Side

Type Count
Vacation Homes 41
Cottages 5
Holiday Apartments 4
Cabin Rentals 2

Use these Quick Filters to Find a Vacation Rental in Shady Side

Pro Tip: Bespokeusatravel makes it easy to compare the best listings on Bespokeusatravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bespokeusatravel homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Shady Side.

Weather in Shady Side

View the weather forecast for Shady Side before booking your Shady Side Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F