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Vacation Homes in Annapolis

Find the vacation homes that appeal to you the most

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The best vacation homes in Annapolis

Check out our selection of great vacation homes in Annapolis

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Fisher House - Downtown Annapolis!

Annapolis

Fisher House - Downtown Annapolis! offers accommodations in Annapolis, 30 miles from Sports Legends Museum at Camden Yards and 30 miles from Baltimore Convention Center.

K
Karen
From
United States
The location is an easy and quick walk to The Naval Academy. The rooms are clean and well organized with plenty of bedding, pillows and towels. Everything is updated! There are even TVs in every room. We felt very much at home while attending our son’s Induction Day at The Naval Academy! We will definitely stay again for future visits.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 8 reviews
Price from
$737.96
1 night, 2 adults
Check availability

Stylish + fresh bungalow 2 blocks from N-MC Stadium

Annapolis

Just a 11-minute walk from Navy-Marine Corps Memorial Stadium and 1.2 miles from Whitehall Gallery, Stylish + fresh bungalow 2 blocks from N-MC Stadium features accommodations in Annapolis with a...

C
Catherine
From
United States
Property was beautiful, everything was clean and well kept! Great location, only a 5 minute drive from downtown Annapolis. Very spacious for 6 people to sleep.
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 11 reviews
Price from
$447.40
1 night, 2 adults
Check availability

The Ultimate cozy escape

Glen Burnie (Near Annapolis)

The Ultimate cozy escape is located in Glen Burnie, just 11 miles from Carroll Park and 12 miles from Sports Legends Museum at Camden Yards.

M
Maria
From
United States
Very nice, clean, convenient and perfect house. I will try to be back.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 13 reviews
Price from
$424.25
1 night, 2 adults
Check availability

Welcome to our newly built house

Glen Burnie (Near Annapolis)

Welcome to our newly built house is located in Glen Burnie, just 12 miles from Pier Six Concert Pavilion and 12 miles from Harbor East Marina.

S
Stefani
From
United States
The place was very nice. It was clean and in great shape.
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 23 reviews
Price from
$385
1 night, 2 adults
Check availability

Walk to the stadium, downtown, West St - close to everything

Annapolis

Walk to the stadium, downtown, West St - close to everything is located in Annapolis, just 2 miles from Annapolis Harbor and 29 miles from Sports Legends Museum at Camden Yards.

B
Brittany
From
United States
The property owner was very attentive, thoughtful, and very accessible. They truly thought about every possible need that we could use or needed. Had drinks ready in the fridge, snacks. It was like we were at home. Cozy and spacious, everyone had their own space, but amazing common area. Very close to everything. I’m absolutely in love with this property.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 9 reviews
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Historic Row Home 1 Block from Gate 1 at USNA

Annapolis

1.1 miles from Annapolis Harbor in Annapolis, Historic Row Home 1 Block from Gate 1 at USNA offers accommodations with access to a hot tub.

V
Venus
From
United States
The location was excellent. The house was very modern, clean, and had all of the amenities that you would want or need.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
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Weems Creek Cottage, Annapolis Waterfront

Annapolis

Weems Creek Cottage, Annapolis Waterfront offers accommodations in Annapolis, 29 miles from Sports Legends Museum at Camden Yards and 29 miles from Baltimore Convention Center.

F
Frances
From
United States
Absolutely gorgeous view! Location is close enough to walk downtown but far enough to be a quiet neighborhood. We even saw a fox on way out to explore one day!! The photo is the view from the window above the bed.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 13 reviews
Check availability

Walk to Everything Historic Arts District

Annapolis

1.9 miles from Annapolis Harbor in Annapolis, Walk to Everything Historic Arts District provides accommodations with access to spa facilities, wellness packages, and beauty services.

A
Ann
From
United States
This charming , 2nd floor apartment was perfect for our girls weekend! The beds were comfortable, the kitchen well stocked and the place had a homey, seaside feel. Restaurants are around the corner and the harbor area is about a 15 minute walk . Off street parking for 2-3 cars was convenient.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 12 reviews
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Vintage Charm: Annapolis Retreat

Annapolis

Offering a garden, Vintage Charm: Annapolis Retreat offers accommodations in Annapolis. The vacation home, set in a building dating from 1909, features free Wifi and free private parking.

T
Tara
From
United States
An extremely charming home in an excellent location. We parked the car and walked all over downtown Annapolis. The rooms were comfortable and the space was generous. Comparable price to the nicer hotels in town. Considering the privacy, the value was excellent.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 11 reviews
Check availability

Neptune By The Water

Annapolis

Neptune By The Water offers accommodations in Annapolis, 10 miles from Annapolis Harbor and 26 miles from Sports Legends Museum at Camden Yards.

D
Diana
From
United States
We were 4 adults traveling for a funeral. It accommodated us very well, with two sitting spaces and an outdoor deck. One member of our group did not do steps well and was able to be accommodated by a door out of the basement. The basement was accommodated with a bedroom, full bathroom with walk in shower, a sitting area and the game space.
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 8 reviews
Check availability
All vacation homes in Annapolis

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Annapolis and surrounding area in the past month

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Popular with guests booking vacation homes in Annapolis

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking vacation homes in Annapolis

Popular with guests booking vacation homes in Annapolis

Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 2 reviews

Popular with guests booking vacation homes in Annapolis

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 13 reviews

Popular with guests booking vacation homes in Annapolis

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

Popular with guests booking vacation homes in Annapolis

Popular with guests booking vacation homes in Annapolis

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking vacation homes in Annapolis

Popular with guests booking vacation homes in Annapolis

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

Popular with guests booking vacation homes in Annapolis

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Enjoy breakfast in Annapolis and nearby

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Scored out of 10, guest rating 7.0
Good - What previous guests thought, 6 reviews

Cozy 2br home w/ parking in downtown Annapolis offers accommodations in Annapolis, 1.4 miles from Annapolis Harbor and 30 miles from Sports Legends Museum at Camden Yards.

Historic Downtown Annapolis Gem Near USNA is located in Annapolis, just 1.6 miles from Annapolis Harbor and 4.6 miles from Annapolis Landing Marina.

Historic Downtown Annapolis w Rooftop Deck is located in Annapolis, just 1.1 miles from Annapolis Harbor and 25 miles from Inner Harbor. This vacation home provides accommodations with a patio.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

Just 1.1 miles from Annapolis Harbor and a 3-minute walk from Maryland State House Of Delegates, Historic Row Home in Downtown Annapolis features accommodations in Annapolis with a garden.

Just a 2-minute walk from William Paca Garden and 500 yards from Chase Lloyd House, Charming Rowhome in Downtown Annapolis features accommodations in Annapolis with a garden.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Renovated Downtown Annapolis w 3-Car Parking is located in Annapolis, just 25 miles from Inner Harbor and 26 miles from Power Plant.

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian is located in Annapolis, just 4.7 miles from Annapolis Landing Marina and a 13-minute walk from Hammond Harwood House.

Just a 2-minute walk from Chase Lloyd House and 500 yards from William Paca Garden, Luxe Row Home Steps to USNA Gate 3 features accommodations in Annapolis with a garden.

Save money on vacation homes in Annapolis and nearby – budget options available

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Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Luxury Rooftop Pool & Dock Steps to Downtown is located in Annapolis, just 8.6 miles from Sandy Point State Park and 19 miles from Six Flags America.

Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 2 reviews

Unique Eastport Bungalow w Yard is located in Annapolis, just 26 miles from Inner Harbor and 26 miles from Power Plant.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 4 reviews

8 Bells Bungalow - Cozy, Stylish, Prime Location is located in Annapolis, just 2.2 miles from Annapolis Harbor and 24 miles from Inner Harbor.

The Goat Locker

Annapolis
Budget options available

2.5 miles from Annapolis Harbor in Annapolis, The Goat Locker provides accommodations with access to a hot tub.

Scored out of 10, guest rating 7.3
Good - What previous guests thought, 11 reviews

Just a 11-minute walk from Navy-Marine Corps Memorial Stadium and 1.2 miles from Whitehall Gallery, Stylish + fresh bungalow 2 blocks from N-MC Stadium features accommodations in Annapolis with a...

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Annapolis Charm 3BR Downtown offers accommodations in Annapolis, 2.2 miles from Annapolis Harbor and 25 miles from Addison Road-Seat Pleasant.

1 Block to USNA Stadium: Modern Annapolis Home! is located in Annapolis, just 2.7 miles from Annapolis Harbor and 25 miles from Inner Harbor.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

Just a 11-minute walk from Navy-Marine Corps Memorial Stadium and 1.1 miles from Whitehall Gallery, Spacious 5 BR house - 5 Min Walk to N-MC Stadium features accommodations in Annapolis with a garden.

Vacation Homes with swimming pools in Annapolis and nearby

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Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

Oasis by the Bay - Waterfront Heated Pool Hot Tub offers accommodations in Annapolis, a 3-minute walk from Bay Ridge Beach and 4.8 miles from Annapolis Harbor.

Great access to the city center. Check these vacation homes in Annapolis and nearby

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Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

All Star Annapolis Retreat - Walk To Stadium is located in Annapolis, just 2.8 miles from Annapolis Harbor and 29 miles from Sports Legends Museum at Camden Yards.

A recently renovated vacation home, 5 bedroom home near downtown Annapolis offers accommodations in Annapolis. This property offers access to a patio, free private parking, and free Wifi.

Offering a garden, NEW! Private, family-friendly home near USNA offers accommodations in Annapolis. This property offers access to a patio, free private parking, and free Wifi.

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking offers accommodations in Annapolis, 1.4 miles from Sparrows Beach and 3 miles from Annapolis Harbor.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Modern Gem Near Historic Annapolis & Naval Academy is located in Annapolis, just 26 miles from Power Plant and 26 miles from Pier Six Concert Pavilion.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Admiral's Retreat - iTrip Annapolis offers accommodations in Annapolis, 3.9 miles from Annapolis Harbor and 27 miles from Carroll Park.

4BR Family Retreat Near Annapolis w Large Yard is located in Annapolis, just 3.8 miles from Annapolis Harbor and 28 miles from Addison Road-Seat Pleasant.

Pet Friendly Retreat Near Downtown Annapolis offers accommodations in Annapolis, 4.5 miles from Annapolis Harbor and 26 miles from Carroll Park.

FAQ about vacation homes in Annapolis

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