Verified
10/10 Excellent
Virginia N.
15 Dec, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Virginia N.
Stayed 3 nights in Dec 2025
Entire home
Upscale Downtown | Loft & Walk to DTA
Photo gallery for Upscale Downtown | Loft & Walk to DTA
Reviews
1010 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 6
Popular amenities
- Kitchen
- Washing machine
- Air-conditioning
- Barbecue grill
- Balcony
- Internet access
Explore the area
Annapolis, MD
- Annapolis City DockPlace, Annapolis City Dock2 min walk
- U.S. Naval AcademyPlace, U.S. Naval Academy2 min walk
- Maryland State HousePlace, Maryland State House3 min walk
- Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)39 min drive
Rooms & beds
2 bedrooms (sleeps 6)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Living Room 1
1 Double Sofa Bed
2 bathrooms, 1 half bathroom
Bathroom 1
Bathtub · Toilet · Shower only
Bathroom 2
Bathtub · Toilet · Shower only
Bathroom 3
Toilet
Spaces
Deck or patio
Kitchen
Office
Balcony
Number of living rooms
Garden
Dining area
About this property
Upscale Downtown | Loft & Walk to DTA
Summary:
Walk out the door and you're in the center of Annapolis. This updated 2-bedroom downtown home has 2.5 baths, two separate living rooms, and a newly renovated kitchen with stainless steel appliances. The primary suite has an ensuite bath, the second bedroom has a king, and the pullout queen in the living room sleeps extra guests. Walk to the Naval Academy, City Dock restaurants, and Main Street shops without touching your car keys. Two Roku TVs, high-speed WiFi, and central AC throughout.
The Space:
BEDROOMS
Two bedrooms on the upper level. The primary suite has a queen bed with an ensuite full bathroom. The second bedroom has a spacious king bed. A queen pullout in the living room provides additional sleeping.
BATHROOMS
2.5 bathrooms — two full baths upstairs near the bedrooms, one half bath on the main level for guests.
KITCHEN
Newly renovated with brand-new stainless steel appliances, cookware, dishes, utensils, and all the basics for cooking at home.
LIVING AREAS
Two separate living rooms give your group space to spread out. The main living room has a Roku TV and a queen pullout couch. The dining room also has a Roku TV, making it a flexible space for meals and entertainment.
OUTDOOR LIVING
Private outdoor space for relaxing — a nice retreat in the middle of downtown.
PARKING
No dedicated parking. Overnight parking available in the Hillman Garage on Main St.
LOCATION
This is as downtown as it gets. Walk to the Naval Academy, City Dock, Main Street shops, and dozens of restaurants. You're in the historic district — everything Annapolis is known for is outside your door.
GOOD TO KNOW
Check-in: 3:00 PM / Checkout: 11:00 AM
Self check-in with smart lock
No parking included
Guest Access:
Entire house
Interaction with Guests:
Text, call, email, or message in the app.
Walk out the door and you're in the center of Annapolis. This updated 2-bedroom downtown home has 2.5 baths, two separate living rooms, and a newly renovated kitchen with stainless steel appliances. The primary suite has an ensuite bath, the second bedroom has a king, and the pullout queen in the living room sleeps extra guests. Walk to the Naval Academy, City Dock restaurants, and Main Street shops without touching your car keys. Two Roku TVs, high-speed WiFi, and central AC throughout.
The Space:
BEDROOMS
Two bedrooms on the upper level. The primary suite has a queen bed with an ensuite full bathroom. The second bedroom has a spacious king bed. A queen pullout in the living room provides additional sleeping.
BATHROOMS
2.5 bathrooms — two full baths upstairs near the bedrooms, one half bath on the main level for guests.
KITCHEN
Newly renovated with brand-new stainless steel appliances, cookware, dishes, utensils, and all the basics for cooking at home.
LIVING AREAS
Two separate living rooms give your group space to spread out. The main living room has a Roku TV and a queen pullout couch. The dining room also has a Roku TV, making it a flexible space for meals and entertainment.
OUTDOOR LIVING
Private outdoor space for relaxing — a nice retreat in the middle of downtown.
PARKING
No dedicated parking. Overnight parking available in the Hillman Garage on Main St.
LOCATION
This is as downtown as it gets. Walk to the Naval Academy, City Dock, Main Street shops, and dozens of restaurants. You're in the historic district — everything Annapolis is known for is outside your door.
GOOD TO KNOW
Check-in: 3:00 PM / Checkout: 11:00 AM
Self check-in with smart lock
No parking included
Guest Access:
Entire house
Interaction with Guests:
Text, call, email, or message in the app.
Add dates for prices
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House Rules
Check in after 3:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
- Do not lock bottom lock on front door - Do not try to unlock the 2 locked owners closets in the unit
Important information
You need to know
Property # 4599678vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Annapolis
Located in Annapolis, this holiday home is in the city centre. Chesapeake Bay Bridge and William Paca House are local landmarks, and some of the area's activities can be experienced at Tose Family Tennis Center and Annapolis Harbor. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Navy-Marine Corps Memorial Stadium.
Annapolis, MD
What's nearby
- William Paca House - 1 min walk - 0.0 km
- Annapolis City Dock - 2 min walk - 0.2 km
- U.S. Naval Academy - 2 min walk - 0.2 km
- Maryland State House - 3 min walk - 0.3 km
- Hammond-Harwood House - 3 min walk - 0.3 km
Getting around
- Odenton Station - 22 min drive
- Fort Meade, MD (FME-Tipton) - 32 min drive
Restaurants
- Starbucks - 4 min walk
- The Choptank - 4 min walk
- O'Brien's Oyster Bar & Seafood Tavern - 4 min walk
- Annapolis Market House - 2 min walk
- Chick & Ruth's Delly - 6 min walk
Frequently asked questions
Is Upscale Downtown | Loft & Walk to DTA pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Upscale Downtown | Loft & Walk to DTA?
As of 11 May, 2026, prices found for a 1-night stay for 2 adults at Upscale Downtown | Loft & Walk to DTA on 2 Nov, 2026 start from S$545, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
What time is check-in at Upscale Downtown | Loft & Walk to DTA?
Check-in begins at 3:00 PM.
What time is check-out at Upscale Downtown | Loft & Walk to DTA?
Checkout is at 11:00 AM.
Where is Upscale Downtown | Loft & Walk to DTA located?
Located in Historic District, this holiday home is within a 10-minute walk of Annapolis City Dock and U.S. Naval Academy. John Smith House and 14 Fleet Street are just steps away.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new windowRating 10 - Excellent. 8 out of 8 reviews
10 - Excellent
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Rating 8 - Good. 0 out of 8 reviews
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Rating 6 - Okay. 0 out of 8 reviews
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2 - Terrible
0
10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
10/10 Excellent
Abbie T.
26 Jun, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Stay
Great stay. Very clean.
Abbie T.
Stayed 1 night in Jun 2025
Verified
10/10 Excellent
Rick H.
24 Mar, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. We walked everywhere we needed to go. Visitors found street parking and a garage a couple blocks away. House was comfortable and felt clean. Good neighborhood and lots to eat close by. Host was very accommodating and easy to reach. Will stay here again.
Rick H.
Stayed 5 nights in Mar 2026
Verified
10/10 Excellent
Gina C.
21 Sept, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
The absolute best location! Super nice clean and perfect for our time in Annapolis! Walkable to everything! Would absolutely recommend!
Gina C.
Stayed 3 nights in Sep 2025
Verified
10/10 Excellent
Bob K.
20 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Jared's place very nicely finished. Convenient location to downtown Annapolis. We will be back!
Bob K.
Stayed 4 nights in Oct 2025
Verified
10/10 Excellent
Brian M.
20 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a wedding in Annapolis this weekend and couldn’t have asked for a better place to stay. What a hidden gem, the place was clean and felt like a “home away from home” the moment we walked in the door. The location is terrific, so close to everything you want to experience while in town. We were only there for 24 hours and wished we had another day to explore and enjoy the sites. Jared was terrific to deal with and we would definitely go back and stay here again if available.Thanks again for a wonderful stay
Brian M.
Stayed 1 night in Jul 2025
Verified
10/10 Excellent
Emily S.
5 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, convenient stay!
I stayed here for the weekend of the 4th of July with some friends. The property was very clean, newly renovated, and fully stocked for all our needs. Communication with the host was always quick and helpful, as were the check in and check out processes. The location couldn’t have been more perfect. Although there wasn’t parking, we were able to find parking in a garage about a ten minute walk away. Considering how proximal this home is to downtown Annapolis, that was totally worth it. We would absolutely stay here again and recommend it to anyone looking for the perfect walkable rental!
Emily S.
Stayed 2 nights in Jul 2025
Verified
10/10 Excellent
Zeb H.
1 Aug, 2025
Zeb H.
Stayed 1 night in Jul 2025
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