Annapolis Vacation Rentals

Aurora Rossi

Are you in a hurry?

Here is a quick list of Vacation Rentals in Annapolis, selected based on their rating

Name of hotel Accommodation Rating Price, $
Chic Condo With Balcony In The Heart Of Annapolis!

8.2 / 10

(11 Reviews)

From 328$
Chase Creek Retreat

8.4 / 10

(6 Reviews)

From 520$
Spectacular Location Two Bedroom State Circle Apartment

8.8 / 10

(9 Reviews)

From 350$
Cozy Downtown Apartment-Naval Academy Vicinity

9.4 / 10

(11 Reviews)

From 263$
Captain'S Retreat! Newly Renovated - Beach House!

10.0 / 10

(1 Reviews)

From 900$

Escape to the charming waterfront city of Annapolis and immerse yourself in the array of vacation rentals that offer a true taste of local living. From historic homes with maritime flair to modern apartments with stunning views, Annapolis has a diverse range of properties to suit every traveler's needs. Whether you seek a cozy retreat for a romantic getaway or a spacious abode for a family vacation, the vacation rentals in Annapolis promise a memorable stay in this historic city by the bay.

Best Annapolis Vacation Rentals

Table of contents

The Master Shipwright Chic Condo With Balcony In The Heart Of Annapolis! The Compass Rose By Leavetown Vacations Chase Creek Retreat Historic Charm Porter Point Spectacular Location Two Bedroom State Circle Apartment Cozy Downtown Apartment-Naval Academy Vicinity Waterfront Escapes Annapolis Bay Ridge Retreat Adventure Annapolis Skyline Sanctuary

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The Master Shipwright

📍 11 Shipwright St

From 1241$

The Master Shipwright Villa is located 12 minutes' walk from the blooming William Paca Garden and 9 minutes' walk away from Banneker-Douglass Museum. There is also an equipped kitchenette with a microwave oven, a fridge, and kitchenware and the rooms offer river views as well.

The venue is 1 km from the centre of Annapolis and in vicinity of St. Anne's Episcopal Church. This accommodation is also set close to Saint Mary Catholic Church. The seafood restaurant Osteria 177 is 8 minutes’ walk away. You can get to the preserved 1774 Hammond-Harwood House in a few minutes by car. The Master Shipwright Villa is a 39-minute drive from Baltimore airport.

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8.2
Very good
11 Reviews

Chic Condo With Balcony In The Heart Of Annapolis!

📍 141 West Street, Annapolis, Md 21401, Us

From 328$

Set close to the historic church "Banneker-Douglass Museum", Chic Condo With Balcony In The Heart Of Annapolis! venue has a patio and Wi-Fi throughout the accommodation. The Kunta Kinte Alex Haley Memorial is 1.1 km from this apartment, while the 18th-century Georgian mansion "William Paca Garden" is 1.2 km away.

Nestled in the historical district, the property is a 10-minute walk from the centre of Annapolis. Guests can find Mission Escape Rooms in the area. American food is served in Light House Bistro within 250 metres from the accommodation. Naval Academy Chapel is a short taxi ride away. Baltimore airport is at a 36-minute driving distance, and West Street & Lafayette Avenue Eastbound bus stop is 100 metres away from the venue.

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8.5
Very good
2 Reviews

The Compass Rose By Leavetown Vacations

📍 1140 Bay Highlands Dr

Located 4.7 km from Annapolis Harbor, the 5-bedroom Compass Rose By Leavetown Vacations Villa offers rooms with lake views. Extras include a microwave oven, a fridge, and kitchenware in a full kitchen and a bath and a shower in a bathroom.

The venue is 15 minutes' drive from Hogshead Sign Shop. You can get to Quiet Waters Park in a few minutes by car. This 40 m² accommodation is 45 km from Baltimore airport.

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Historic Charm

Immerse yourself in the rich history of Annapolis by staying in a beautifully restored historic vacation rental. From colonial-era cottages to elegant townhouses, these properties offer a glimpse into the city's storied past. Enjoy period details, cozy fireplaces, and unique architectural features that transport you to a bygone era while still providing modern comforts for a truly unique stay.

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8.4
Very good
6 Reviews

Chase Creek Retreat

📍 1542 Briarcliff Road

From 520$

Chase Creek Retreat Villa is situated around a 15-minute ride from the shopping mall "Annapolis Towne Centre" in Annapolis and offers accommodation with a fully furnished kitchen. The property has 3 bedrooms and 3 bathrooms.

Annapolis Harbor is approximately 15 minutes' drive away. You can get to Maryland State House in a few minutes by car. Baltimore airport is a 35-minute ride away.

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Porter Point

📍 2929 Southaven Dr

Located a 25-minute walk from Broad Creek Park, Porter Point Villa offers accommodation with views of the lake. Guests, staying at this venue, can use a fully equipped kitchen with a fridge, an oven, and kitchenware to prepare home-cooked meals.

The villa is 10 minutes' drive from the air museum "Historic London Town and Gardens". You can get to Waterworks Park in a few minutes by car. The nearest airport is Baltimore airport, 35 km from the accommodation.

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8.8
Excellent
9 Reviews

Spectacular Location Two Bedroom State Circle Apartment

📍 94 State Circle

From 350$

Located 5 minutes’ drive to Annapolis Harbor, this spacious Spectacular Location Two Bedroom State Circle Apartment features a fully-fitted kitchen for those who want to self-cater. The nearest bus stop Saint Johns Street & College Avenue Far-side Northbound is 150 metres away, while ARTFX Gallery of Fine Crafts and Arts can be reached within 500 metres.

The venue is located in Annapolis, a 5-minute walk from its centre. Guests can find Mission Escape Rooms in the area. The dessert restaurant serving American cuisine is 250 metres away. Quiet Waters Park is a short taxi ride away and the historic church "Banneker-Douglass Museum" is close, too. The nearest airport is Baltimore airport, 45 km from this spacious accommodation in Annapolis.

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Waterfront Escapes

Experience the quintessential Annapolis lifestyle by choosing a waterfront vacation rental overlooking the serene Chesapeake Bay. Wake up to breathtaking views of sailboats and lighthouses, and spend your days exploring the waterfront promenades and historic harbors. Whether you prefer a luxurious beach house or a cozy bungalow by the water, these rentals offer a front-row seat to Annapolis' maritime beauty.

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9.4
Excellent
11 Reviews

Cozy Downtown Apartment-Naval Academy Vicinity

📍 21 Randall Street B

From 263$

Cozy Downtown Apartment-Naval Academy Vicinity is a spacious venue set 300 metres from Main Street and 1.8 km from Annapolis Harbor. The spacious accommodation also includes a full kitchen with a microwave, a fridge, and kitchenware.

Major Annapolis sights, such as Annapolis Historic District and Historic Annapolis Museum and Store are located not far away. The centre of Annapolis is about 1 km away. Serving a variety of dishes, The Federal House Bar & Grille and Sammys Downtown Deli are 150 metres away. Take a few minutes' cab ride to see Chesapeake Bay Bridge. The nearest airport is Baltimore, 45 km from Cozy Downtown Apartment-Naval Academy Vicinity, and Saint Johns Street & College Avenue Far-side Northbound bus station is 10 minutes' walk away.

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Annapolis Bay Ridge Retreat

📍 190 W Lake Dr

From 994$

Annapolis Bay Ridge Retreat Villa is situated about 10 minutes by car from Truxton City Park in Annapolis and offers accommodation with a fully furnished kitchen. The venue is fitted with 5 bedrooms and 4 bathrooms.

The villa is 10 minutes' drive from Maryland Federation of Art. The centre of Annapolis is at 5 km. You can get to Annapolis Historic District in a few minutes by car. This 645 m² property is 45 km from Baltimore airport.

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Adventure Annapolis

📍 732 Shore Drive

From 411$

Adventure Annapolis Villa is within a few steps of the air museum "Historic London Town and Gardens" and London Town Publik House. This accommodation also has 3 bedrooms and includes a fully equipped kitchen with a microwave, a fridge, and kitchenware.

Thurgood Marshall Memorial is 7 km away and Annapolis Harbor is 7 km from the venue. You can get to Annapolis Historic District in a few minutes by car. The nearest airport is Baltimore airport, 45 km from Adventure Annapolis Villa.

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Quaint Cottages

Escape the hustle and bustle of everyday life by choosing a quaint cottage for your Annapolis vacation. Tucked away in peaceful neighborhoods or nestled amidst lush gardens, these charming rentals provide a cozy retreat for relaxation and rejuvenation. Enjoy private outdoor spaces, well-appointed interiors, and personalized touches that make your stay feel like a home away from home.

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10
Excellent
2 Reviews

Skyline Sanctuary

📍 31 Pinkney St

Skyline Sanctuary Villa is situated only 1.8 km from Annapolis Harbor in Annapolis and offers accommodation with a full kitchen. 2 bedrooms and 2 bathrooms are comprised in this venue.

Popular points of interest near the villa include Mission Escape Rooms and Saint Mary Catholic Church. It is a 39-minute drive from Baltimore airport and a 5-minute drive to Ellen O. Moyer Nature Park at Back Creek. Market House and Harvest Wood Grill can be found 200 metres from the property. You can get to Maryland World War II Memorial in a few minutes by car. Saint Johns Street & College Avenue Far-side Northbound bus stop is approximately 400 metres away.

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10
Excellent
1 Reviews

Captain'S Retreat! Newly Renovated - Beach House!

📍 3534 Newport Avenue

From 900$

The 4-bedroom Captain'S Retreat! Newly Renovated - Beach House! Venue is less than approximately 6 km from Annapolis Maritime Museum. There is a fully furnished kitchen with a refrigerator, an oven, and glassware while 2 bathrooms are included as well.

The accommodation is 15 minutes' drive from Annapolis Harbor. The villa is set right next to free beaches. You can get to Beverly Triton Nature Park in a few minutes by car. This 334 m² property is 50 km from Baltimore airport.

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9.6
Excellent
9 Reviews

Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier!

📍 1709 River Road

From 559$

The venue is located a 10-minute ride from Broadneck Park and about 3.1 km from Hackett Point. There is a fully equipped kitchen with a microwave and kitchenware while 1 bathroom are included as well.

An own beach lies nearby. You can get to Broadneck Peninsula Trail in a few minutes by car. This 125 m² accommodation is 40 km from Baltimore airport.

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Modern Luxury

Indulge in contemporary luxury by selecting a modern vacation rental equipped with top-of-the-line amenities and stylish decor. From sleek downtown lofts to upscale penthouses, these properties cater to travelers seeking a chic and sophisticated stay in Annapolis. Enjoy open-concept living spaces, designer kitchens, and panoramic city views that elevate your vacation experience to new heights.

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9.3
Excellent
58 Reviews

Gaia House

📍 102 Louis Drive

From 137$

Gaia House Villa is situated around 10 minutes' drive from Truxton City Park in Annapolis and offers accommodation with a fully equipped kitchen. It also includes 2 bedrooms and 1 bathroom.

The venue is 10 minutes' drive from Maryland State House. The centre of Annapolis is at 3 km. Guests can enjoy Italian dishes in Ledo Pizza located 650 metres away. You can get to Annapolis Harbor in a few minutes by car. The nearest airport is Baltimore airport, 40 km from Gaia House Villa.

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Third Street Retreat

This Third Street Retreat Villa is located not far from Annapolis Harbor. Extras include a microwave, a fridge, and kitchenware in a full kitchen and a walk-in shower, a separate toilet, and a bath in a bathroom.

Maryland State House is nearly a 5-minute drive away, while Annapolis Historic District is 1.3 km from the venue. The centre of Annapolis is at 2 km. Guests can try American meals in the bar Boatyard Bar & Grill located 250 metres away. Chance Boatyard is a short walking distance away. This 181 m² accommodation is 45 km from Baltimore airport.

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Eastport Haven

A 20-minute stroll from Eastport Haven Villa takes guests to Maryland State House, while Annapolis Harbor is a 7-minute walk away. The venue is composed of 3 bedrooms, a fully-fitted kitchen with a microwave, a refrigerator, and kitchenware and 3 bathrooms.

The villa is 2 km from the centre of Annapolis and in vicinity of Annapolis Maritime Museum. This property is also set close to Chance Boatyard. Boatyard Bar & Grill includes American cuisine, situated 250 metres away. You can get to the historic church "Banneker-Douglass Museum" in a few minutes by car. The nearest airport is Baltimore airport, about 45 km away.

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Coastal Getaways

Embrace the coastal charm of Annapolis by booking a vacation rental near the city's sandy beaches and scenic shorelines. Whether you prefer a cozy beachfront cottage or a spacious seaside villa, these properties offer a perfect blend of relaxation and recreation. Spend your days sunbathing on the sand, exploring quaint seaside towns, and savoring fresh seafood at waterfront restaurants for an idyllic coastal getaway in Annapolis.

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9.8
Excellent
9 Reviews

Annapolis Escape Steps To Harbor Backs To Gate 1

📍 126 Prince George Street #2

Annapolis Escape Steps To Harbor Backs To Gate 1 Villa is situated merely 0.6 km from Historic Annapolis Museum and Store in Annapolis and offers accommodation with a fully-fitted kitchen. This has 1 bedroom and 1 bathroom.

The venue is 1 km from the centre of Annapolis and in vicinity of Maryland State House. Annapolis Yacht Basin is 12 minutes' walk away. Guests can enjoy American delicacies prepared at Pip's Dock Street Dogs, just 200 metres from the villa. U.S. Naval Academy is nearby as well. Baltimore airport is the nearest one and it is 45 km from this property.

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8
Very good
3 Reviews

Admiral'S Glen

📍 33 N Glen Avenue

From 315$

A 25-minute stroll from Admiral'S Glen Villa takes guests to the preserved 1774 Hammond-Harwood House, while The Chesapeake Children's Interactive Museum is an 18-minute walk away. This venue has 3 bedrooms, 2 bathrooms, and a full kitchen with a microwave, a refrigerator, and kitchenware.

The centre of Annapolis is nearly 2 km from the accommodation. The restaurant Carlson's Donuts is located 400 metres away. You can get to Annapolis Harbor in a few minutes by car. This 214 m² property is 40 km from Baltimore airport.

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Charming Annapolis Townhome

📍 19 Morris Street

From 896$

The 2-bedroom Charming Annapolis Townhome is less than just 1.4 km from the undergraduate college "United States Naval Academy Museum". Extras include a microwave oven, a fridge, and kitchenware in a kitchen and a bathtub, a separate toilet, and a shower in a bathroom.

The venue is 1 km from the centre of Annapolis and in vicinity of Mission Escape Rooms. At this villa you'll be within a 16-minute stroll of The Kunta Kinte Alex Haley Memorial. Guests can enjoy American meals in Chesapeake Brewing Co, which is about 200 metres away. Popular points of interest near the accommodation include ARTFX Gallery of Fine Crafts and Arts. Charming Annapolis Townhome is 40 km from Baltimore airport.

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8.3
Very good
12 Reviews

Bayridge House By Quiet Waters, Thomas Point Parks

📍 903 Old Annapolis Neck Road B

Located 10 minutes’ drive to the Harwood Big Brice House, this spacious Bayridge House By Quiet Waters, Thomas Point Parks Apartment features a fully equipped kitchen for those who want to self-cater. The venue is set 3.3 km from Annapolis Harbor.

The apartment is set 4 km from the center of Annapolis. American meals are served at the bar Annapolis Smokehouse and Tavern. Quiet Waters Park is a short taxi ride away. Guests can access Baltimore airport within 41 minutes by car.

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9.8
Excellent
12 Reviews

Weems Creek Cottage, Annapolis Waterfront

📍 705 Arundel Place

Weems Creek Cottage, Annapolis Waterfront is situated around 3 km from Ego Alley in Annapolis and offers accommodation with a full kitchen. At this venue parking is available on site.

Saint Paul Lutheran Church lies within a 7-minute walk of the villa. The centre of Annapolis is less than 2 km away. At Bean Rush Cafe guests will savour the best of American specialities. You can get to Maryland World War II Memorial in a few minutes by car. Baltimore airport is around a 34-minute drive away, and the property lies within 650 metres of Rowe Boulevard & Taylor Avenue Northbound bus station.

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10
Excellent
1 Reviews

Harrison Hall

📍 514 Chesapeake Ave

From 917$

Harrison Hall Villa is set a mere 1.3 km from Hogshead Sign Shop and represents a 4-bedroom venue with a patio. The property also comes with a fully furnished kitchen, which is equipped with a microwave oven, a fridge, and kitchenware.

The centre of Annapolis is nearly 2 km from the villa. Guests will be 1.1 km from Annapolis Historic District. A seafood restaurant can offer American menu and is set 350 metres away. You can get to Maryland State House in a few minutes by car. Harrison Hall Villa offers an accommodation within 40 minutes by car from Baltimore airport.

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7
Good
1 Reviews

The Admiral'S Retreat

📍 219 West Lake Drive

Located approximately 10 minutes' drive from Annapolis Harbor, The Admiral'S Retreat Villa offers accommodation with views of the lake. The venue is equipped with 6 bedrooms plus a fully furnished kitchen with a refrigerator, an oven, and kitchenware.

The property is 10 minutes' drive from Quiet Waters Park. The centre of Annapolis is less than 5 km away. You can get to St. John's College in a few minutes by car. The Admiral'S Retreat Villa offers an accommodation within 46 minutes by car from Baltimore airport.

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9.4
Excellent
6 Reviews

Waterfront Annapolis Cottage: Fire Pit & Pier

From 259$

Waterfront Annapolis Home Fire Pit And Fishing Pier offers a cosy accommodation, around 10 minutes by car from Broadneck Peninsula Trail. Extras include an oven, a cooktop, and kitchenware in a full kitchen and a separate toilet, a bath, and a shower in a bathroom.

The venue is 10 minutes' drive from Sandy Point State Park. You can get to Hackett Point in a few minutes by car. This 130 m² villa is 40 km from Baltimore airport.

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9
Excellent
1 Reviews

Usna Getaway

📍 316 Burnside St 208

Situated 7 km from Chesapeake Bay Bridge, Usna Getaway Apartment provides accommodation with Wi-Fi throughout the venue. There is a fully equipped kitchen with a microwave oven, a fridge, and kitchenware provided for a comfortable everyday stay.

The property is located in Annapolis, a 15-minute walk from its centre. You can also visit Maryland Federation of Art after a 17-minute stroll. Several restaurants such as Blackwall Hitch Annapolis and Boatyard Bar & Grill are within 450 metres from Usna Getaway Apartment. The Chesapeake Children's Interactive Museum is a short taxi ride away. Baltimore airport is situated at 45 km distance from the apartment.

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9
Excellent
1 Reviews

Pet-Friendly Annapolis Home Walk To Beach!

📍 1252 Creek Dr

Located within 6 km of Annapolis Harbor, the 3-bedroom Pet-Friendly Annapolis Home Walk To Marina! offers rooms with garden views. This accommodation also comes with a fully-fitted kitchen complete with a microwave oven, a refrigerator, and kitchenware, so you can easily make your favourite dishes.

The venue is 15 minutes' drive from St. Anne's Episcopal Church. You can get to The Chesapeake Children's Interactive Museum in a few minutes by car. The nearest airport is Baltimore, 45 km from the villa.

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10
Excellent
1 Reviews

Anchors Aweigh

📍 180 Prince George St

From 813$

The 4-bedroom Anchors Aweigh Villa is less than just 1.9 km from Annapolis Harbor. This accommodation also comes with a fully furnished kitchen complete with a microwave, a refrigerator, and kitchenware, so you can easily make your favourite dishes.

Chesapeake Harbour is approximately 10 minutes' drive away. The venue lies 10 minutes' walking distance from Annapolis city centre. Restaurant The Federal House Bar & Grille is within 300 metres away. Anchors Aweigh Villa is close to the preserved 1774 Hammond-Harwood House and Annapolis Historic District. Baltimore airport is located 45 km from the property.

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Location