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Upscale Downtown | Loft & Walk to DTA

Photo gallery for Upscale Downtown | Loft & Walk to DTA

Living area
Exterior
Room
Outdoor dining
Dining

Reviews

10 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 61408 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space
  • Barbecue grill

Explore the area

View in a map
Annapolis, MD
  • Place, Annapolis City Dock
    ‪2 min walk‬
  • Place, U.S. Naval Academy
    ‪2 min walk‬
  • Place, Maryland State House
    ‪3 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪32 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

Toilet · Shower only

Bathroom 3

Toilet

Spaces

Deck or patio
Kitchen
Office
Balcony
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.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
Barbecue grill

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House Rules

Check in after 3:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

Annapolis

Located in Annapolis, this holiday home is in the city centre. William Paca House and 48 Fleet Street 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.
View more Holiday homes in AnnapolisOpens in a new window
Map
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

  • ‪The Choptank - ‬4 min walk
  • ‪Starbucks - ‬4 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬4 min walk
  • ‪Buddy's Crabs & Ribs - ‬3 min walk
  • ‪Annapolis Market House - ‬2 min walk

Frequently asked questions

Is Historic Downtown Annapolis Gem 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 25 Mar 2026, prices found for a 1-night stay for 2 adults at Upscale Downtown | Loft & Walk to DTA on 25 May 2026 start from £194, 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 Historic Downtown Annapolis Gem?

Check-in begins at 3:00 PM.

What time is check-out at Historic Downtown Annapolis Gem?

Checkout is at 10:00 AM.

Where is Historic Downtown Annapolis Gem 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 window
Rating 10 - Excellent. 7 out of 7 reviews
Rating 8 - Good. 0 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Virginia N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was perfect for 2 couples and you could not ask for a better location
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Abbie T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay

Great stay. Very clean.
Stayed 1 night in Jun 2025
Verified

10/10 Excellent

Gina C.

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!
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Bob K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Jared's place very nicely finished. Convenient location to downtown Annapolis. We will be back!
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Brian M.

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
Stayed 1 night in Jul 2025
Verified

10/10 Excellent

Emily S.

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!
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Zeb H.

Stayed 1 night in Jul 2025

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