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The best vacation homes in Shady Side

Check out our selection of great vacation homes in Shady Side

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Luxe Chesapeake Bay Getaway Less Than 20 Mi to Annapolis!, hotel in Shady Side

Luxe Chesapeake Bay Getaway Less Than 20 Mi to Annapolis! offers accommodations in Shady Side, 29 miles from Addison Road-Seat Pleasant.

The home was charming. Backyard is Chesapeake Bay! Owners extremely nice and accommodating. Would definitely recommend to anyone. Will stay here again.
Scored 9.6
9.6
Rated exceptional
Exceptional
10 reviews
Calloway Drive Retreat, hotel in Shady Side

Calloway Drive Retreat offers accommodations in Deale, 21 miles from Annapolis Harbor and 29 miles from Addison Road-Seat Pleasant.

Absolutely a great place to stay. We received the door code via email the day prior to check-in. The house is fully equipped to include a fully equipped kitchen. The grocery is about a 7-minute drive from the house. There is an isolated beach about a 10-minute walk away from the house. Washer and dryer worked well. Check-out was easy.
Scored 9.3
9.3
Rated wonderful
Wonderful
7 reviews
Searenity Stays, hotel in Shady Side

A recently renovated vacation home, Searenity Stays offers accommodations in Edgewater.

The house is fully equipped with everything you need - from an extensive kitchen to extra linens and reusable bags. It's well laid out and feels very roomy. It's in a cosy, quiet neighborhood next to to a state park but convenient to Annapolis and all the amenities that come with a city. It was perfect for a group of friends and would be equally perfect for a family.
Scored 9.8
9.8
Rated exceptional
Exceptional
9 reviews
Vintage Charm: Annapolis Retreat, hotel in Shady Side

Offering a garden, Vintage Charm: Annapolis Retreat offers accommodations in Annapolis. The vacation home, set in a building dating from 1909, features free Wifi and free private parking.

Close to downtown Historic updated house Beautiful clean home Super responsive host
Scored 10
10
Rated exceptional
Exceptional
5 reviews
Family-sized Contemporary in Spacious Neighbourhood, hotel in Shady Side

Family-sized Contemporary in Spacious Neighbourhood is located in Annapolis, just 6.6 miles from Annapolis Harbor and 24 miles from Carroll Park.

Area was convenient and safe. The house was good space for our family. Beds were comfortable. Nice touches...snacks, coffee station, water bottles.
Scored 9.2
9.2
Rated wonderful
Wonderful
6 reviews
Annapolis Vacation Home 2 Mi to Quiet Waters Park, hotel in Shady Side

Annapolis Vacation Home 2 Mi to Quiet Waters Park is located in Annapolis, just 1.8 miles from Carrs Beach and 3.2 miles from Annapolis Harbor.

The house was just great for all of us. Very well maintained and very clean. We wrrived really really late that night but we still have to pay for few hours of late checkout. I just thought since we arrived late, we can offset to the late checkout. Other than that, our stay was great.
Scored 9.4
9.4
Rated wonderful
Wonderful
12 reviews
Gaia House, hotel in Shady Side

Gaia House offers accommodations in Annapolis, 3.7 miles from Annapolis Harbor and 24 miles from Addison Road-Seat Pleasant.

Just like home! Very cute and stylish.
Scored 9.5
9.5
Rated exceptional
Exceptional
31 reviews
Private Single Family Home Close to Both Water and Downtown!, hotel in Shady Side

Private Single Family Home Close to Both Water and Downtown! is located in Annapolis, just 1.2 miles from Carrs Beach and 3.1 miles from Annapolis Harbor.

Beautifully furnished home with super comfortable beds! The kitchen and bathrooms were well stocked. Easy access to downtown and the Naval Academy. The owner was very responsive.
Scored 9.4
9.4
Rated wonderful
Wonderful
5 reviews
Waterfront Annapolis Home Fire Pit and Fishing Pier, hotel in Shady Side

Waterfront Annapolis Home Fire Pit and Fishing Pier is located in Annapolis, just 8.7 miles from Annapolis Harbor and 26 miles from Inner Harbor.

Very quiet and peaceful. Loved the decor and the use of the dock.
Scored 9.3
9.3
Rated wonderful
Wonderful
7 reviews
Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!, hotel in Shady Side

Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER! is a recently renovated villa in Annapolis where guests can make the most of the garden and barbecue facilities.

Everything! Seeing deer on my morning run was awesome. The property was beautiful and quiet.
Scored 9.8
9.8
Rated exceptional
Exceptional
8 reviews
All vacation homes in Shady Side
Looking for a vacation home?
Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.