Places to stay near Downtown Annapolis Partnership

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Top-rated holiday rentals near Downtown Annapolis Partnership

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Top guest favourite

The exterior of a charming historic building features a welcoming front porch adorned with seating. Lush green trees and blooming flowers enhance the inviting atmosphere. American flags are displayed, highlighting the traditional character of the neighborhood.

Home in Annapolis

Elegant & Authentic Annapolis

Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.

4.99 out of 5 average rating, 156 reviews

Top guest favourite

The exterior of a historic townhome is showcased, featuring red brick walls and black shutters. Lush greenery and colorful flowers enhance the garden area. A flag may be seen hanging from the building, set against a clear blue sky.

Townhouse in Annapolis

Historic 3 Bedroom Downtown Annapolis Townhome

Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, Downtown Restaurants, Bars, Shopping, and Festivals. Enjoy and relax on your large private, fenced-in patio or in your modern living room. While the restaurant scene is mouth-watering in Annapolis, you can also stay "home" and cook in your gourmet kitchen. Explore all that Annapolis has to offer from the comfort of your home away from home! No on-site parking but lots of off.

4.95 out of 5 average rating, 213 reviews

Top guest favourite

Cottage in Annapolis

Secluded Cottage_ A+ Amenities in Historic Dwntwn

Beautifully restored 1928 cottage w/ open floor plan & vaulted ceilings provide a homey vibe Enjoy Historic Annapolis Towncenter in your backyard Jack & Jill bath separates queen bedrooms. Comfortable full-size daybed = 3beds Hardwood floors adorn common areas Gourmet kitchen w/ extensive granite countertops, breakfast bar & amenities Dining table & chairs, extra-large comfy couch nestled between 2 chaise lounge chairs, 55" Roku tv, electric FP, towels, linens, pvt laundry, and more!

4.93 out of 5 average rating, 228 reviews

Top guest favourite

The layout of the home is depicted in an illustrated floor plan, showcasing three distinct areas. Each level features various rooms, including bedrooms, a living space, and a kitchen area, with labels indicating the functions of different spaces.

Home in Annapolis

Villa Annapolitana • Parking 1 min • USNA 4 min

Our 1700s home offers a perfect blend of luxury and comfort. With three beautiful bedrooms, three bathrooms, and a sleek lounge area, it’s a perfect place to relax and unwind. The fully stacked kitchen is ready and waiting for you to cook a perfect meal and enjoy a glass of wine. The location is ideal, with the US Naval Academy just a 5-minute walk away. If you are looking for a peaceful escape or a fun vacation, our property has something for everyone. ✔ King Beds ✔ Smart TVs ✔ Sport E

4.97 out of 5 average rating, 154 reviews

Top guest favourite

A modern kitchen features a large marble island with seating for several guests. White cabinetry and a stainless steel stove create a clean aesthetic. Natural light filters in through multiple windows, illuminating the thoughtful decor, including a chandelier and a vase with fresh flowers on the island.

Home in Annapolis

Gorgeous Historic Downtown Annapolis House

USNA grad-owned, this 5 bedroom & 3.5 bathroom elegant house is located in the heart of downtown Annapolis (1 block from USNA Gate 3 & from St. John's College). Cable, WIFI, linens, towels, and a parking pass for one car included (street parking only). Pet requests considered (permission required in advance; there is a $500 pet fee if approved). Beautiful backyard for entertaining. We ask guests to treat the space as if they are guests in our home. We look forward to hosting you!

4.98 out of 5 average rating, 160 reviews

Top guest favourite

Home in Annapolis

USNA downtown house with garage parking EV 3bd/2ba

1992 grad’s downtown home near USNA with GARAGE PARKING & EV charger! Top listing as “Guest’s Favorite” for consistent 5 star ratings. Best location on a private one way street behind Iron Rooster. Enjoy all the modern touches including smART FrameTV with local artist’s work, bluetooth speaker, keyless entry, Nest thermostat, 2 Novaform mattress beds and remodeled kitchen/bathrooms. Garage parking is for small car. Famous photo wall out front. New deck and fence

4.95 out of 5 average rating, 106 reviews

Top guest favourite

The front exterior of the home features vibrant, blooming flowerbeds with a variety of blue and pink flowers. Two hanging planters with yellow flowers adorn the entryway, while a charming red door stands out against the yellow walls. A small seating area with dark chairs is visible on the porch.

Home in Annapolis

Historic & sunny home steps from USNA/downtown

This beautiful and cozy 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City Dock and Gate 1 (main gate) of the US Naval Academy. Filled with sunlit, spacious rooms and equipped with numerous amenities (incl. gas fireplace), this home can sleep up to 8 (on 4 beds in the 3 bedrooms and 1 futon in a private room in the basement) and offers a combination of location and charm that is hard to beat!

5.0 out of 5 average rating, 202 reviews

Top guest favourite

A modern kitchen is highlighted by sleek white cabinetry and a large island with seating for four. Stainless steel appliances are positioned for convenience, and natural light fills the space through a window overlooking the backyard.

Townhouse in Annapolis

Beautiful Downtown Annapolis Townhome!

Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , 3 and 1/2 Baths , Wonderful Upgraded Mattresses that will ensure a great nights sleep, Big screen TV's Back yard courtyard with gas firepit. And the best part....... Walking distance to Downtown Annapolis with Shopping , Dining and much more bring the whole family to this great place with lots of room for fun.

5.0 out of 5 average rating, 119 reviews

Guest favourite

Home in Annapolis

The Very Best location - 50 Steps from Main Street

Truly in the HEART of downtown we are 50 steps from Main Street, City Dock and all the action. Featuring the best front porch in town with 3 bedrooms we sleep 6 maximum. We offer an open floor plan, two full baths, kitchen and the best front porch in town. We may not be the fanciest rental in town but is a great comfortable house is an unbelievable location. Everything you need nothing you don't.

4.82 out of 5 average rating, 124 reviews

Top guest favourite

Flat in Annapolis

Charming, Chic Downtown Annapolis Apartment #1

In the heart of Downtown Annapolis. One block from Main Street/West Street/Church Circle. Close proximity to USNA, Ego Alley, Eastport, State House, shops, galleries, restaurants/bars and all other DTA amenities. This private apartment has an open floor plan and is elegantly decorated (with a modern twist). One Full Bathroom with tiled shower. One Bedroom with walk-in closet (with W/D).

4.91 out of 5 average rating, 120 reviews

Top guest favourite

A serene outdoor patio area features manicured hedges and a stone path. A seating arrangement is visible, surrounded by greenery. A colorful flag and artwork hang on the fence, while flowering trees add a natural touch to the space, providing a cozy atmosphere.

Home in Annapolis

Historic Downtown in-law suite

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit. Twin bed can be set up and made up at guest request.

4.96 out of 5 average rating, 260 reviews

Guest favourite

A modern kitchen is presented with white cabinetry and grey accents. Stainless steel appliances, including a refrigerator and microwave, are integrated. A large island with a light stone countertop serves as a central feature, complemented by overhead pendant lights that illuminate the workspace.

Home in Annapolis

Chic Renovation On Fleet Street

We welcome you at our newest listing in the heart of downtown Annapolis . This chic renovation is a stylish landing spot for anything that brings you to downtown Annapolis . We feature an open floor plan, 2 bedrooms, 1.5 baths and a small city patio . Walkable to everything ! Our guests use Hillman city garage for parking ( pay )

4.88 out of 5 average rating, 113 reviews