Annapolis Vacation Rentals

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Browse Select Annapolis Vacation Homes

Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (2)
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. The large slace and outdoor activity allowed for a lot of team building and we had a blast llaying pickle ball and basketball with each other. We wish we coukd have spent more time there."
The price is CA $846
CA $1,945 total
includes taxes & fees
May 14 - May 15
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Cheerful 3-Bedroom House in Downtown Annapolis
10.0 out of 10, Exceptional, (10)
"We were looking for a place to spend our Thanksgiving and this was perfect! Great location close to downtown Annapolis. Marina was awesome - she was super responsive and took time during the holiday weekend to answer our questions. We loved that there were two places to hang out. Kitchen was well stocked. Lots of extra towels and blankets. General notes: The sofa bed in the basement is not a pull out as expected but is technically a twin bed and the bunk bed is actually a twin with a trundle...
Cheerful 3-Bedroom House in Downtown Annapolis
Property grounds
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (6)
"Was a super comfortable spot my 5 friends and I. Super comfy couches and beds, nice TV, well appointed kitchen. Took a nice walk down to the water in the am. Would stay again!"
The price is CA $355
CA $770 total
includes taxes & fees
May 14 - May 15
Charming Cottage with Hot Tub 1 Block from the Bay
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Property grounds
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
10.0 out of 10, Exceptional, (62)
"I’ve reviewed this home several times, still 5/5"
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Fridge, microwave, oven, stovetop
Charming Historic Townhouse Steps From USNA
10.0 out of 10, Exceptional, (12)
"My sister and I stayed while attending an event at the US Naval Academy. It was a quick, pleasant walk back and forth and always refreshing to come "home" and spend some quiet relaxing time together after a day out in town. Like a mini refuge!"
Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (179)
"This home is a charming and cozy historic property with a private courtyard in back with garden lights. The location is perfect right across from the Naval Academy and a couple blocks walk to the waterfront and center of town."
Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (43)
"Laura’s house is so nice and comfortable. It has everything you could need and more. The backyard is such a great space. My one and only complaint/warning is that the front bedrooms were noisy at night because of the cars/traffic going by. This is nothing a white noise machine can’t fix. We would still definitely stay there again!("
Recently Renovated Annapolis Home - Conveniently Located
Property grounds
7 mins away from Downtown Annapolis
10.0 out of 10, Exceptional, (5)
"The home was very clean and beautifully set up. The property managers were very helpful and communicative. they even had complimentary snack, beverages, and even a hand written note with a wine bottle. Bathrooms were clean and stocked with everything incase you forgot something at home. Everyone enjoyed the home, we were planning our next visit before we even left!"
7 mins away from Downtown Annapolis
Beach
Private Cottage on gated estate
10.0 out of 10, Exceptional, (15)
"Such a lovely and peaceful home! There are three bedrooms upstairs with a hallway bathroom and the 2nd bathroom is on the ground floor with the kitchen and family area. The house is very kid friendly. I'm disgusted by all things "kids" so we hid most of what was left out. It was a thoughtful gesture for those who partake though. There is also a lovely front yard play area where we were able to relax outside on chairs once we arrived. The beds and couch were all super comfortable. We were there...
Private Cottage on gated estate
Fridge, microwave, oven, stovetop
Waterfront Estate Annapolis - Beautiful Views - Dock & Boat Slip - Pet Friendly
10.0 out of 10, Exceptional, (1)
"The view and house were amazing, and the owners were so easy to get in touch with and super accommodating. A great place to stay."
Waterfront Estate Annapolis - Beautiful Views - Dock & Boat Slip - Pet Friendly
Fridge, microwave, oven, stovetop
La Maison - Stunning waterfront views with pool
10.0 out of 10, Exceptional, (76)
"The property was exactly as advertised. Clean, well equipped and comfortable. Our party of 2 families, with kids from 3-7 greatly enjoyed our stay and visiting the local area. We hope to be back again in the warmer weather when we can use the pool!"
La Maison - Stunning waterfront views with pool
Property grounds
Free parking Historic Union House Downtown with private patio
10.0 out of 10, Exceptional, (20)
"Very nice property with excellent location. Well stocked kitchen and backyard seating area."
Free parking Historic Union House Downtown with private patio
Pool
Lakefront dog-friendly home with private outdoor pool, pool spa, dock & grill
10.0 out of 10, Exceptional, (3)
Lakefront dog-friendly home with private outdoor pool, pool spa, dock & grill
Fridge, microwave, oven, stovetop
Anne's Cottage House
10.0 out of 10, Exceptional, (1)
"Great for families - easy to get to DTA and Eastport restaurants!"
Anne's Cottage House
Terrace/patio
Spacious Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces
10.0 out of 10, Exceptional, (12)
"The property was perfect — great location, layout, furniture, appliances, dishes, etc. It was also super easy coordinating check-in/check-out, access, etc. — the team was very responsive. It was an excellent stay and experience!"
Spacious Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces
View from property
Beautiful Cottage Style Home in Quiet Downtown Neighborhood
10.0 out of 10, Exceptional, (2)
"We loved this place so much we booked it again! Highly recommend!!"
Beautiful Cottage Style Home in Quiet Downtown Neighborhood
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (78)
"Liz, the host, was one of the nicest and most accommodating hosts I have ever had the pleasure to work with. She allowed me and a few of my bridesmaids to get ready in her home for my wedding a few blocks away. It was the perfect location. Fully equipped with whatever we needed, meticulously well-decorated and maintained, and surprisingly spacious for our needs. The beds were very comfortable for some much needed rest. Liz’s garden is incredible. I definitely recommend a spring visit for that...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop
USNA home
10.0 out of 10, Exceptional, (2)
"This property is great location to Naval Stadium and downtown Annapolis. We walked to everything. On street parking wasn't a problem. There is a parking garage a block away."
USNA home
Fridge, microwave, oven, stovetop
Great location, free parking
10.0 out of 10, Exceptional, (24)
"The house is in a great location near the water and close to downtown Annapolis. The house itself was perfect for our group and had everything we needed. The owner, Gibson, was very helpful and communicative and if this house was ever available again would definitely stay there."
Great location, free parking
Dining
3 Story Stunner in Murray Hill <1 mile from USNA!
10.0 out of 10, Exceptional, (13)
"The location and the house were perfect. Spacious and beautiful!"
The price is CA $373
CA $1,137 total
includes taxes & fees
May 27 - May 28
3 Story Stunner in Murray Hill <1 mile from USNA!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Annapolis

Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (2)
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. The large slace and outdoor activity allowed for a lot of team building and we had a blast llaying pickle ball and basketball with each other. We wish we coukd have spent more time there."
The price is CA $846
CA $1,945 total
includes taxes & fees
May 14 - May 15
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (179)
"This home is a charming and cozy historic property with a private courtyard in back with garden lights. The location is perfect right across from the Naval Academy and a couple blocks walk to the waterfront and center of town."
Directly Across from Gate One & Steps from the Waterfront
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (25)
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio Apartment
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Annapolis Vacation Homes information

Number of reviews
536
Accommodation
254 Vacation Homes
Lowest Price
CA $355
Highest Price
CA $846

Recent Reviews in Annapolis
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