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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, 159 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, 214 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, 157 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, 161 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, 109 reviews
Top guest favourite
A bright living area features a comfortable sofa and a patterned armchair, arranged around a wooden coffee table. A rug adds warmth to the hardwood floor, while ample natural light enters through multiple windows. The kitchen, adjacent to the living space, is equipped with modern appliances.
Apartment in Annapolis

Funky Uptown Apt meets Downtown - Hist District

Location location location where Uptown meets Downtown in the Historic District. 1/2 block to Dinner Under The ✨ , First Sunday Arts. Tsu, 49 West, Level in the front yard Ramshead, Stan and Joes and Reynold's Tavern in the back. EVERYTHING Annapolis (USNA, Stadium, Statehouse, Ego Alley, Main St, Eastport) is walking distance from this unique 2nd floor unit w elevated deck for morning coffee as Jazz wafts in, full kitchen, w/d, clawfoot shower/tub, MBR with Queen.

4.96 out of 5 average rating, 128 reviews
Top guest favourite
A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.
Apartment in Annapolis

1st Floor Condo in Annapolis

This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock (limited access) and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

4.96 out of 5 average rating, 180 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, 205 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, 120 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).

4.9 out of 5 average rating, 125 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, 268 reviews

Popular amenities for holiday rentals near Downtown Annapolis Partnership

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near Downtown Annapolis Partnership

Downtown Annapolis Partnership

57 locals recommend

United States Naval Academy

121 locals recommend

Rams Head Tavern

127 locals recommend

Annapolis Maritime Museum & Park

97 locals recommend

Annapolis City Dock

93 locals recommend

William Paca House and Garden

75 locals recommend

Apartment rentals with wifi

Guest favourite
A welcoming living area features two brown leather sofas adorned with blue patterned cushions. A wooden coffee table sits atop a blue geometric rug, and a small potted plant decorates the table. Natural light streams in from two windows beside the front door.
Apartment in Annapolis

Capts Qrtrs - Awesome downtown Annapolis location!

4.86 out of 5 average rating, 193 reviews
Guest favourite
A wooden walkway extends along the water, bordered by low posts and a railing. Boats are docked in the distance, with a gentle curve of the marina visible. Potted plants and striped decor can be seen, contributing to the waterfront atmosphere.
Apartment in Annapolis

Annapolis @Gate 1 steps to the Harbor Free parking

4.91 out of 5 average rating, 153 reviews
Guest favourite
A spacious living area is presented with a blue reclining sofa facing a large wall-mounted television. Warm wood cabinetry complements the kitchen area in the background, illuminated by soft lighting. A cozy electric fireplace adds warmth, creating an inviting space for relaxation.
Apartment in Annapolis

Anchors Away

4.85 out of 5 average rating, 110 reviews
Top guest favourite
Apartment in Annapolis

Captains Quarters | Waterfront & Pool

4.98 out of 5 average rating, 124 reviews
Top guest favourite
A bright living room features large windows dressed with light curtains, allowing natural light to fill the space. A comfortable sofa and armchair are arranged around a sleek coffee table, with shelves displaying books and decorative items, contributing to a welcoming atmosphere.
Apartment in Annapolis

New Downtown Annapolis Condo With Free Parking

4.98 out of 5 average rating, 166 reviews
Top guest favourite
A bright living area features stylish seating arrangements with two blue sofas and a central ottoman. A wall-mounted television is positioned beneath decorative shelving. An open kitchen space is visible, showcasing modern bar stools and a dining area bathed in natural light from a nearby window.
Apartment in Annapolis

Renovated Apt In Historic Dist w/2 Parking Spots

4.94 out of 5 average rating, 454 reviews
Guest favourite
A spacious living area is depicted with plush teal seating arranged around a coffee table. A modern entertainment unit is positioned against a wall, while large sliding doors open to a private balcony. Natural light enhances the warm tones of the decor.
Apartment in Annapolis

Annapolis Condo-1 bedroom King

4.96 out of 5 average rating, 131 reviews
Superhost
A modern living area features a sleek flat-screen television mounted above a stone fireplace. On either side, wooden shelving units are filled with decorative items and books. The ambient light from the fireplace creates a cozy atmosphere, complemented by neutral wall colors.
Apartment in Inner Harbor

Historic Federal hills urban lifestyle

4.86 out of 5 average rating, 291 reviews

Family-friendly house rentals

Guest favourite
Home in Annapolis

Historic Downtown House with Off Street Parking

4.9 out of 5 average rating, 147 reviews
Guest favourite
An inviting living room showcases a light-colored sectional sofa adorned with decorative pillows. A wooden coffee table, accompanied by a small ottoman, sits on warm hardwood flooring. Natural light filters through the window near the front door, which features glass panels.
Home in Annapolis

Cozy 2br home w/ parking in downtown Annapolis

4.92 out of 5 average rating, 368 reviews
Guest favourite
Home in Annapolis

The Very Best location - 50 Steps from Main Street

4.82 out of 5 average rating, 125 reviews
Guest favourite
The exterior of a charming two-story row house is presented, featuring light blue siding and black shutters. A pink front door is framed by decorative greenery, while a small bench sits on the red brick walkway. Potted plants add a welcoming touch to the entrance.
Home in Annapolis

Charming Renovated Historic Home Downtown wParking

4.91 out of 5 average rating, 243 reviews
Guest favourite
A tranquil bedroom features a spacious bed adorned with a patterned throw and neatly arranged pillows. A modern lamp and decorative mirror enhance the ambiance, while natural light enters through a unique shaped window. A soft towel is elegantly rolled on the bed.
Home in Annapolis

The Navy House-Walk or Shuttle Downtown! 3 bd

4.93 out of 5 average rating, 206 reviews
Guest favourite
A modern kitchen features a large island with seating for four. Sleek cabinets and stainless steel appliances create a functional cooking space. Unique pendant lights hang above the island, complementing the stylish countertop. The open layout allows visibility to the living area beyond.
Home in Annapolis

Fleet St Retreat in Downtown - Great Location!

4.91 out of 5 average rating, 125 reviews
Top guest favourite
A charming house is depicted, featuring a light blue exterior with white trim. A front sunroom with numerous windows invites natural light. A white picket fence encloses a small garden area, while a brick pathway leads to a red garage door and a tree with blossoming flowers.
Home in Annapolis

Sophisticated & Spacious Historic Home w/ Parking!

4.96 out of 5 average rating, 178 reviews
Top guest favourite
The front porch features a welcoming red door and blue Adirondack chairs. Stone steps lead to the porch, adorned with a large pot of yellow flowers and a matching red planter. White railings frame the porch, enhancing its charming appearance.
Home in Annapolis

Charming house; walk to everywhere in Annapolis

4.99 out of 5 average rating, 187 reviews

Apartment rentals with air conditioning

Guest favourite
The exterior of a spacious home is shown, featuring a combination of stone and siding. A large driveway leads to a two-car garage, while multiple windows provide natural light. A balcony above the entrance offers additional outdoor space, surrounded by green lawns and landscaping.
Flat in Annapolis

Private Annapolis Inlaw Apartment

4.89 out of 5 average rating, 373 reviews
Superhost
Aerial view of a marina surrounded by a cluster of homes and colorful trees, with numerous boats docked along the waterfront. The scenic landscape features water and docks, with the horizon showcasing more boats and buildings in the distance.
Flat in Annapolis

Charming Eastport

4.77 out of 5 average rating, 305 reviews
Top guest favourite
A charming corner of a historic building is showcased, featuring a prominent American flag flanked by potted greenery. The view extends down a quiet street, with a glimpse of an adjacent building in the background, enhancing the setting of Annapolis's historic district.
Flat in Annapolis

CIRCA 1885-Historic Annapolis-USNA GATE 1

4.99 out of 5 average rating, 133 reviews
Guest favourite
The entrance features a welcoming front door adorned with a decorative wreath, flanked by windows with shutters. A small stairway leads up to the door, with a concrete path that is surrounded by greenery.
Flat in Annapolis

King George Hideaway

4.92 out of 5 average rating, 122 reviews
Superhost
A spacious bedroom features a large bed with striped bedding and decorative pillows. A colorful upholstered bench sits at the foot of the bed. Soft light is provided by two bedside lamps, and natural light filters in through the windows with white trim.
Flat in Annapolis

Gybeset Eastport Inn

4.88 out of 5 average rating, 307 reviews
Top guest favourite
A charming three-story house is depicted, with light green siding and distinct architectural features. Large windows allow for natural light, and flower pots with hydrangeas are placed along the front, enhancing the welcoming appearance of this property.
Flat in Annapolis

Perfect Eastport location

4.98 out of 5 average rating, 148 reviews
Guest favourite
An open kitchen and living area showcases wooden cabinetry and a white stove. A small dining table with light-colored chairs is positioned in the center. Comfortable seating includes a dark sofa and a black ottoman, complemented by a rug featuring ornate patterns.
Flat in Annapolis

Hideaway in the Middle of Everything AYC 2+BR apt

4.78 out of 5 average rating, 123 reviews
Top guest favourite
A bright yellow building features large blue shutters and a welcoming entrance. A sign is placed outside, and vibrant flowers border the steps. In the background, another structure is visible, along with flags proudly displayed.
Flat in St. Michaels

Blue Crab Lodge

4.98 out of 5 average rating, 162 reviews

Other great holiday rentals near Downtown Annapolis Partnership

Top guest favourite
Guest house in Annapolis

Coastal Waterfront 1 Bedroom Cottage

5.0 out of 5 average rating, 226 reviews
Top guest favourite
Cottage in Annapolis

Charming Cottage 2 parking spot easy walk downtown

4.94 out of 5 average rating, 214 reviews
Guest favourite
A cozy living room features a soft beige sofa adorned with decorative pillows, complemented by a wooden coffee table. A fireplace is set into a white-washed wall, while a painting hangs above. Natural light fills the space, highlighting the warm wooden flooring.
Townhouse in Annapolis

Historic Downtown Property

4.81 out of 5 average rating, 315 reviews
Top guest favourite
A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.
Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

4.97 out of 5 average rating, 472 reviews
Top guest favourite
Cottage in Annapolis

Weems Creek Cottage, Annapolis Waterfront

4.98 out of 5 average rating, 167 reviews
Top guest favourite
A screened porch features a hanging bench swing with cushions in shades of blue and nautical motifs. A small chair stands nearby, adorned with a decorative pillow. Tall curtains frame the space, providing a relaxed and inviting atmosphere surrounded by greenery.
Cottage in Annapolis

Charming City Retreat. Walk-harbor, eateries.USNA

4.87 out of 5 average rating, 118 reviews
Top guest favourite
A vibrant yellow door is framed by classic dark shutters, contributing to the home's charming exterior. A decorative knocker is visible, and a blue planter with greenery sits on the steps beside a wrought iron railing.
Townhouse in Annapolis

3 BR - Historic Downtown home with Rooftop Deck!

4.98 out of 5 average rating, 132 reviews
Top guest favourite
A serene waterfront view is captured, featuring lush green grass leading to a private patio area with a hot tub. In the background, a rainbow arches over the water, framed by a cloudy sky. The cozy apartment stands nearby, enhancing the tranquil setting.
Guest suite in Annapolis

Bay View Studio Apartment

4.97 out of 5 average rating, 100 reviews