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Find vacation rentals that suit your style
Our top choices for Shady Side condo rentals
1. Upscale Condo in Annapolis w/Private Parking
Upscale Condo in Annapolis w/Private ParkingHistoric District
10.0 out of 10, Exceptional, (4 reviews)
10/10
Exceptional
(4 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
Scott P.
$610 nightly
The price is $695
$695 total
Nov 16 - Nov 17
Total with taxes and fees
2. Chapel Gate 3BR Steps to City Dock & Naval Academy
Chapel Gate 3BR Steps to City Dock & Naval AcademyHistoric District
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
"Very cute home in great proximity to naval academy"
"Very cute home in great proximity to naval academy"JENNIFER E.
$481 nightly
The price is $544
$544 total
Nov 8 - Nov 9
Total with taxes and fees
3. Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.Eastport
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)
"Excellent place to stay!"
"Excellent place to stay!"Michaell M.
$575 nightly
The price is $627
$627 total
Nov 8 - Nov 9
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Learn more about Shady Side
Love dining out, parks, and museums? Get away to Shady Side!
Top reviews in Shady Side
Anchored Inn at Hidden Harbour Marina
Anchored Inn at Hidden Harbour MarinaDeale
10/10 Excellent
We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.
We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.
Rico
SpringHill Suites by Marriott Annapolis
SpringHill Suites by Marriott AnnapolisAnnapolis
10/10 Excellent
Perfect for what we needed
Perfect for what we needed
Julie
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MDAnnapolis
10/10 Excellent
The property is a great location. An easy drive to DTA and convenient to the mall and restaurants west of Annapolis.
The property is a great location. An easy drive to DTA and convenient to the mall and restaurants west of Annapolis.
Anonymous traveler
Historic Inns of Annapolis
Historic Inns of AnnapolisHistoric District
10/10 Excellent
Lovely property in the heart of Annapolis. Quiet yet convenient to downtown. Connor was awesome! He took care of our every need.
Lovely property in the heart of Annapolis. Quiet yet convenient to downtown. Connor was awesome! He took care of our every need.
Robert
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel AnnapolisAnnapolis
10/10 Excellent
Excellent and friendly service provided to hotel guests. From the front desk to restaurant, to housekeeping and also the Transport shuttle!
Excellent and friendly service provided to hotel guests. From the front desk to restaurant, to housekeeping and also the Transport shuttle!
Celina
TownePlace Suites by Marriott Annapolis
TownePlace Suites by Marriott AnnapolisAnnapolis
10/10 Excellent
This is the second time I’ve gone there. I’ve loved it the first time and came back again and picked the same hotel. This place serves a great breakfast. A lot of space and is clean. The staff are very accommodating to whatever you need.
Thank you again
Jamila
This is the second time I’ve gone there. I’ve loved it the first time and came back again and picked the same hotel. This place serves a great breakfast. A lot of space and is clean. The staff are very accommodating to whatever you need.
Thank you again
Jamila
Jamila
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHGAnnapolis
10/10 Excellent
Clean, Comfortable, and great service.
Clean, Comfortable, and great service.
John
Sonesta ES Suites Annapolis
Sonesta ES Suites AnnapolisEdgewater
10/10 Excellent
This was my first time at this brand of hotel so I didn’t have any expectations. I was surprised in a good way. The room was well appointed for a short stay and very clean. The kitchen was fully stocked. The gym was small but had everything I needed for a couple of workouts. There was also a very well stocked breakfast in the morning. I have special food needs and I found plenty to eat. The entire staff was pleasant and helpful. I had never been there before but will definitely go back.
This was my first time at this brand of hotel so I didn’t have any expectations. I was surprised in a good way. The room was well appointed for a short stay and very clean. The kitchen was fully stocked. The gym was small but had everything I needed for a couple of workouts. There was also a very well stocked breakfast in the morning. I have special food needs and I found plenty to eat. The entire staff was pleasant and helpful. I had never been there before but will definitely go back.
Sheree
Holiday Inn Express & Suites Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHGAnnapolis
10/10 Excellent
Great breakfast and hot tub
Great breakfast and hot tub
Marc
Knapps Narrows Marina & Inn
Knapps Narrows Marina & InnSherwood
10/10 Excellent
We had a wonderful two night stay at the hotel. The marina is beautiful with nightly rentals if needed. Our first stay and we will return. Great staff very helful. If you are looking for a peacefull,tranquil location you will like it.
We had a wonderful two night stay at the hotel. The marina is beautiful with nightly rentals if needed. Our first stay and we will return. Great staff very helful. If you are looking for a peacefull,tranquil location you will like it.
Stan and Joan
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis DowntownAnnapolis
10/10 Excellent
This is always a great stay. The location is really good, the staff is very friendly and professional, the bar is nice and the appetizers are delicious. My room is always spotless and the bath is spacious and bright!
This is always a great stay. The location is really good, the staff is very friendly and professional, the bar is nice and the appetizers are delicious. My room is always spotless and the bath is spacious and bright!
Robert
Courtyard by Marriott Annapolis
Courtyard by Marriott AnnapolisAnnapolis
10/10 Excellent
This hotel is incredible, from the service to the amenities. We visit Annapolis to see family every single summer, and this was the first time that we stayed at the Courtyard by Marriott, and it will not be the last. We had some issues with the hotel that we normally stay at, and had to change hotels last minute. We were about 2 hours from Annapolis and were desperate for rooms, and they were more than catering to our needs.
We were traveling in a party of five and upon arrival, after hearing...
This hotel is incredible, from the service to the amenities. We visit Annapolis to see family every single summer, and this was the first time that we stayed at the Courtyard by Marriott, and it will not be the last. We had some issues with the hotel that we normally stay at, and had to change hotels last minute. We were about 2 hours from Annapolis and were desperate for rooms, and they were more than catering to our needs.
We were traveling in a party of five and upon arrival, after hearing...
Lillian
TownePlace Suites Bowie Town Center
TownePlace Suites Bowie Town CenterBowie
10/10 Excellent
We enjoyed our stay and were very pleased with the location. We were able to reach all our points of interest within a reasonable time so will definitely stay again when in the area!
We enjoyed our stay and were very pleased with the location. We were able to reach all our points of interest within a reasonable time so will definitely stay again when in the area!
Monica
Fairfield Inn & Suites By Marriott Annapolis
Fairfield Inn & Suites By Marriott AnnapolisAnnapolis
10/10 Excellent
Property opened 5/2024. Still pristine when I visited with my fam. Free breakfast was very good. Gym is as you would expect in a Marriott- great.
Staff working out some kinks in the check in process. Understandable to me as this is a new team.
Nasty surprise when we checked in to learn there was a $30 parking fee. The lot is self park and an open lot. This was not disclosed when I booked on Expedia. I will not return to this property for this reason.
Property opened 5/2024. Still pristine when I visited with my fam. Free breakfast was very good. Gym is as you would expect in a Marriott- great.
Staff working out some kinks in the check in process. Understandable to me as this is a new team.
Nasty surprise when we checked in to learn there was a $30 parking fee. The lot is self park and an open lot. This was not disclosed when I booked on Expedia. I will not return to this property for this reason.
ronald
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique HotelAnnapolis
10/10 Excellent
Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!
Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!
Reyna
Courtyard by Marriott Bowie
Courtyard by Marriott BowieBowie
10/10 Excellent
Each time I come in this area this is where I will stay. The accommodations are excellent and location is convient
Each time I come in this area this is where I will stay. The accommodations are excellent and location is convient
Patricia
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
10/10 Excellent
The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...
The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...
Christina
Frequently Asked Questions
How much do condos in Shady Side cost?
Condos in Shady Side range from $543 to $695 per night. This will give you lots of room for the entire family at a price that's easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your condo in Shady Side with Expedia?
We think that vacations shouldn't be difficult, so if you're looking for condos at an affordable rate, Expedia can help. Stick to the budget and go for something small and affordable, or book 5-star accommodations and really spoil your crew. Our search filters make it a breeze to secure a property in Shady Side that checks your boxes.
How can I find cheap condos in Shady Side?
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What is there to do in Shady Side near my condo?
The best travel accessory is a well-planned to-do list. Shadyside Park is a great place to kick off your adventures in Shady Side.