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The best holiday homes in Shady Side

Check out our pick of great holiday homes in Shady Side

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

Featuring sea views, Luxe Chesapeake Bay Getaway Less Than 20 Mi to Annapolis! is located in Shady Side, 46 km from Addison Road-Seat Pleasant.

Scored 9.6
9.6
Rated exceptional
Exceptional
10 reviews
Calloway Drive Retreat, hotel in Shady Side

Set in Deale, 35 km from Annapolis Harbor and 46 km from Addison Road-Seat Pleasant, Calloway Drive Retreat offers air-conditioned accommodation with a patio and free WiFi.

Scored 9.3
9.3
Rated superb
Superb
7 reviews
Searenity Stays, hotel in Shady Side

Set in Edgewater in the Maryland region and Triton Beach reachable within 700 metres, Searenity Stays offers accommodation with free WiFi, a children's playground, a private beach area and free...

Everything is spotlessly clean and it is a very very comfortable house. The location is lovely, in a very quiet residential neighbourhood. It is the nicest holiday rental we have ever stayed in.
Scored 9.8
9.8
Rated exceptional
Exceptional
9 reviews
Vintage Charm: Annapolis Retreat, hotel in Shady Side

Situated in Annapolis, 3 km from Annapolis Harbor and 46 km from Carroll Park, Vintage Charm: Annapolis Retreat offers a garden and air conditioning.

Scored 10
10
Rated exceptional
Exceptional
5 reviews
Family-sized Contemporary in Spacious Neighbourhood, hotel in Shady Side

Located in Annapolis and only 11 km from Annapolis Harbor, Family-sized Contemporary in Spacious Neighbourhood provides accommodation with garden views, free WiFi and free private parking.

The house is fantastic. It's vast and perfectly furnished. The area is also great—lots of trees and super quiet. It's 10 minutes drive from the center of Annapolis. Host very helpful and friendly.
Scored 9.2
9.2
Rated superb
Superb
6 reviews
Annapolis Vacation Home 2 Mi to Quiet Waters Park, hotel in Shady Side

Situated in Annapolis, 2.9 km from Carrs Beach and 5.2 km from Annapolis Harbor, Annapolis Vacation Home 2 Mi to Quiet Waters Park offers air conditioning.

This was one of the loveliest homes we've ever stayed in. It was super comfortable. There was plenty of room for everyone. Everything worked. We even loved the way it was decorated. Asem, our host was great at communicating and super responsive. We also like that all the house information was provided way ahead of time so that we could all arrive on our own schedules. It was great! Thank you!
Scored 9.4
9.4
Rated superb
Superb
12 reviews
Gaia House, hotel in Shady Side

Featuring air-conditioned accommodation with a patio, Gaia House is located in Annapolis. This property offers access to a balcony, free private parking and free WiFi.

Great property. Stayed here as a family. Great base for us. Local supermarket (across the road) was brilliant and had everything we needed. There was a small problem with the Air conditioning and the owner went over and above to sort this out for us. Owners were so friendly and kind - cannot fault Gaia House - great value for money.
Scored 9.5
9.5
Rated exceptional
Exceptional
31 reviews
Private Single Family Home Close to Both Water and Downtown!, hotel in Shady Side

Featuring air-conditioned accommodation with a patio, Private Single Family Home Close to Both Water and Downtown! is located in Annapolis.

The RBNB is well equip and everything was easy to found and identify Thank you
Scored 9.4
9.4
Rated superb
Superb
5 reviews
Waterfront Annapolis Home Fire Pit and Fishing Pier, hotel in Shady Side

Located in Annapolis, 14 km from Annapolis Harbor and 42 km from Inner Harbor, Waterfront Annapolis Home Fire Pit and Fishing Pier offers air conditioning.

Scored 9.3
9.3
Rated superb
Superb
7 reviews
Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!, hotel in Shady Side

Boasting lake views, Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER! features accommodation with a garden and a patio, around 14 km from Annapolis Harbor.

Very nice and clean. Quiet and well maintained.
Scored 9.8
9.8
Rated exceptional
Exceptional
8 reviews
All holiday homes in Shady Side
Looking for a holiday home?
Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.