Search for vacation rentals in Annapolis.
Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Annapolis area to find the perfect spot for your vacay.
901 Old Annapolis Neck Rd |
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901 Old Annapolis Neck RdAnnapolis, MD$3,600
Vacation Rentals, Unknown NEW!
-4 bedrooms (1 is a master suite) -3 bathrooms -Eat in kitchen with granite countertops -Large living room -Basement can function as an in-law suite with a kitchenette area, a laundry area and it's...... |
11A Heritage Ct |
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11A Heritage CtAnnapolis, MD$2,250
Vacation Rentals, Unknown NEW!
Recently renovated 2-bedroom townhome located in the city of Annapolis, MD. This home offers a comfortable living space with 2 bedrooms and 1.5 bathrooms, perfect for those seeking a...... |
973 Round Top Dr |
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973 Round Top DrAnnapolis, MD$2,900
Vacation Rentals, Unknown NEW!
Nice 3 Br 2 Full Bath, unfinished basement, Blue Ribbon School District, Water privileged community... |
1301 President St |
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1301 President StAnnapolis, MD$2,450
Vacation Rentals, Unknown
Live the true Annapolis lifestyle in this picturesque cape cod home. Nestled on a corner lot with a white picket fence, this adorable home is everything you could hope for. The main living area has...... |
2111 Bay Front Ter |
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2111 Bay Front TerAnnapolis, MD$4,495
Vacation Rentals, Unknown
Fantastic four-bedroom, 3.5-bath home in the Tydings on the Bay, Podickory Point Community of Annapolis. Huge open plan living area, dining space, and a beautifully updated kitchen with granite...... |
Ash Ln |
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Ash LnAnnapolis, MD$2,475
Vacation Rentals, Unknown
The house sits on a sunny 0.7 acre lot in the Saint Margaret's area of Annapolis, near NSA Annapolis, only 3 miles from downtown and 2 miles south of route US 50 and route MD 2. Naturally well-lit,...... |
1605 Cananaro Ct |
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1605 Cananaro CtAnnapolis, MD$1,750
Vacation Rentals, Unknown
Cape St Claire area across from Bay Head Park. Lower 1 bedroom with 1 bath and full living room and dining area. Complete Kitchen and private laundry room. Separate entrance with separate deck and...... |
1709 Robin Hood Rd |
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1709 Robin Hood RdAnnapolis, MD$3,200
Vacation Rentals, Unknown
Totally renovated cottage in park like setting of Epping Forest. Beautiful hardwood floors, open concept with new kitchen and 2.5 bathrooms. Tons of new windows overlooking wooded ravine. Wood...... |
E Winchester Rd |
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E Winchester RdAnnapolis, MD$2,500
Vacation Rentals, Unknown
Serenity and Privacy! This remodeled 2 bedroom, 1 bath single family home is the perfect place to call home. Everything has been completely updated. New flooring, new windows, new paint, new...... |
2 Highland Ave |
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2 Highland AveAnnapolis, MD$2,850
Vacation Rentals, Unknown
Don't miss your chance to live in this adorable 2 bedroom and 1 bathroom home in Annapolis. Home has large fenced in yard and huge attic for storage. Washer and Dryer is located in the large...... |
1228 Ramblewood Dr |
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1228 Ramblewood DrAnnapolis, MD$5,800
Vacation Rentals, Unknown
Newly renovated beautifully furnished single-family house. In a great quiet neighborhood and school area. For long term and short term (minimum one month). Must summit application with background...... |
3737 Thomas Point Rd |
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3737 Thomas Point RdAnnapolis, MD$115
Vacation Rentals, Unknown
This contemporary waterfront house is perfect for a summer getaway. Located near the communities of Bay Ridge and Arundel on the Bay, Thomas Point is it's own hidden gem. This home has a small...... |
897 Chestnut Tree Dr |
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897 Chestnut Tree DrAnnapolis, MD$6,000
Vacation Rentals, Unknown
Freshly painted* Two-car garage colonial in a quiet cul-de-sac offers 3 generous sized bedrooms w/ walk-in closets, 3 full baths and a half bath.* High quality laminated floor on main level....... |
506 Ferry Point Rd |
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506 Ferry Point RdAnnapolis, MD$5,300
Vacation Rentals, Unknown
Spacious five bedroom, four bathroom (2 full + 2 half) Colonial home in the Wild Rose community of Annapolis. Updated eat-in kitchen with granite counters, propane stove with dual ovens, white...... |
967 Old Annapolis Neck Rd |
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967 Old Annapolis Neck RdAnnapolis, MD$3,400
Vacation Rentals, Unknown
House is for rent in the Annapolis/Hillsmere Area. Entire house recently renovated. Neighborhood Features: -On cul-de-sac street -Across from Hillsmere Elementary school -5 mins from Downtown...... |
1201 Bay Ridge Ave |
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1201 Bay Ridge AveAnnapolis, MD$2,375
Vacation Rentals, Unknown
BOATER'S DELIGHT 1201 BAY RIDGE AVENUE, ANNAPOLIS, MD 21403. FOR RENT $2,375/month. Cozy and comfortable little Cottage located on the desirable Eastport Peninsula in the water privileged Parkwood...... |
245 King George St |
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245 King George StAnnapolis, MD$6,500
Vacation Rentals, Unknown
Recently renovated 5 bedroom, 3.5 bathroom stately home located in the heart of historic downtown Annapolis. Only one block from USNA and one block from St. John's College. Just around the corner...... |
1257 Pine Hill Dr |
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1257 Pine Hill DrAnnapolis, MD$3,395
Vacation Rentals, Unknown
Renovated, single level three bedroom two full bathroom single-level Rancher home with a carport and large fully fenced back yard and deck in the water-privileged Cape St Claire Community of...... |
216 Parker Ave |
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216 Parker AveAnnapolis, MD$3,495
Vacation Rentals, Unknown
Fantastic four-bedroom, three-bathroom single-family home with a fully fenced-in backyard in the Parole Heights community of Annapolis. Large, open-plan living area, dining, and a beautiful kitchen...... |
1252 Pram Pl |
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1252 Pram PlAnnapolis, MD$4,600
Vacation Rentals, Unknown
Pictures coming soon . Newly upgraded 4br 2.5 bath home in desirable Annapolis Cove. White oak hardwood floors throughout. A large fenced-in backyard, perfect for entertaining. Water privileges...... |
209 Claude St |
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209 Claude StAnnapolis, MD$4,500
Vacation Rentals, Unknown
Immaculate, newly-renovated, three-bedroom, two full bathroom single family corner house in West Annapolis. Great full-size front porch as you walk up the home. Spacious living room, dining area,...... |
1 N Cherry Grove Ave |
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1 N Cherry Grove AveAnnapolis, MD$2,475
Vacation Rentals, Unknown
One of a kind historic 2 bedroom rental in Annapolis with garage. Updated modern recessed led lighting and ceiling fans (e.g. Haiku.) High ceilings. Wood floors. New heat pump for AC and heat....... |
324 Windell Ave |
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324 Windell AveAnnapolis, MD$3,795
Vacation Rentals, Unknown
Immaculate three-level, four-bedroom, three-and-a-half bathroom single-family home with one car garage in the Homewood community of Annapolis. Open-plan first-floor living and dining space with...... |
1018 Wells Ave |
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1018 Wells AveAnnapolis, MD$2,995
Vacation Rentals, Unknown
Spacious, three-bedroom, 2.5-bathroom, 3-level single-family home with a fully fenced back yard and off-street parking in the heart of Eastport, Annapolis. Open living area with a modern kitchen,...... |
106 Lancaster Ct |
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106 Lancaster CtAnnapolis, MD$2,350
Vacation Rentals, Unknown
VERY PRIVATE AND PEACEFUL ,A NEWLY RENOVATED ,SUNNY TWO BED ROOM ,ONE BATH ,WALKOUT BASEMENT APARTMENT, ALL NEW VERY THING APPLIANCES CABINETS GRANITE COUNTER TOPS .LOCATED IN A QUIET NEIGHBORHOOD...... |
Locust Ave |
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Locust AveAnnapolis, MD$2,100
Vacation Rentals, Unknown
In the popular neighborhood of Homewood. Currently occupied this month so... Property viewing by arrangement with the landlord after a rental application. PLEASE READ ALL DETAILS. THANK YOU. Full...... |
Lancaster Ct |
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Lancaster CtAnnapolis, MD$2,350
Vacation Rentals, Unknown
VERY PRIVATE AND PEACEFUL ,A NEWLY RENOVATED ,SUNNY TWO BED ROOM ,ONE BATH ,WALKOUT BASEMENT APARTMENT, ALL NEW VERY THING APPLIANCES CABINETS GRANITE COUNTER TOPS .LOCATED IN A QUIET NEIGHBORHOOD...... |
14 Silopanna Rd |
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14 Silopanna RdAnnapolis, MD$2,495
Vacation Rentals, Unknown
Great 4 bedroom, 1 bath cape cod with hardwood floors and central AC. Completely remodeled kitchen, open plan living area and large fully fenced back yard with storage shed. Superb location, close...... |
145 King George St |
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145 King George StAnnapolis, MD$2,700
Vacation Rentals, Unknown
This 3-bedroom, 1.5-bath townhome is conveniently located near USNA Gate 1, St. John's College, and the State Capitol Building. It offers complete walkability to all of downtown Annapolis's...... |
2189 Glenfield Rd |
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2189 Glenfield RdAnnapolis, MD$3,100
Vacation Rentals, Unknown
Spacious 4 bedroom 3 full bath rancher style home with full basement, patio area and upper decks with woodland views in the Rolling Knolls community of Annapolis. Hardwood floors, large family room...... |
93 Great Lake Dr |
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93 Great Lake DrAnnapolis, MD$3,000
Vacation Rentals, Unknown
Ranch style home situated minutes from the water! Kitchen with granite counter, stainless appliances and ceramic tile floor! Hardwood floors throughout upper level. Master bedroom with attached...... |
108 Marquise Ln |
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108 Marquise LnAnnapolis, MD$6,500
Vacation Rentals, Unknown
Available 6/1/24 - Fully Furnished Short term/Long term Rental! This 3 bedroom/3.5 bathroom home features: open concept living, a chef's kitchen, Full downstairs with an extra an queen bed,...... |
2720 Gingerview Ln |
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2720 Gingerview LnAnnapolis, MD$3,500
Vacation Rentals, Unknown
Large 2 bedroom, 4 full bathroom, 3 story townhome in Riva Trace. Townhome has 2 balconies perfect for relaxing and looking out at the South River during the summer months. Each bedroom has its own...... |
1114 Smithville St |
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1114 Smithville StAnnapolis, MD$2,195
Vacation Rentals, Unknown
AVAILABLE April 19th - Updated 2 BR 1.5 bath home. Off Street parking, fence rear area for privacy. Do9considered with reference and pet fee. MIN CREDIT SCORE OF 625 AND GROSS HOUSEHOLD INCOME OF...... |
711 Shelton Ave |
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711 Shelton AveAnnapolis, MD$4,095
Vacation Rentals, Unknown
Uptown living with 4 spacious floors of living space. New in 2015, this open concept 4 Bedroom/4.5 Bath Extra Wide End Unit Townhome features hardwood floors throughout the Main Level, a cozy gas...... |
3730 Thomas Point Rd |
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3730 Thomas Point RdAnnapolis, MD$4,800
Vacation Rentals, Unknown
Waterfront home in Oakwood Community w/ unsurpassed views of S. River and Bay. New gourmet kitchen w/ island. Main level MBR bath. Spacious open living area, F/R with wood-burning F/P. Hard wood FL...... |
Beach Dr |
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Beach DrAnnapolis, MD$1,500
Vacation Rentals, Unknown
lower apartment unit (B) for lease in the Hillsmere Community. Monthly rent $1500.00 + $75-electric assessment. Cable and all other utilities included. Available beach pass. Two + miles to downtown...... |
233 Old Mill Bottom Rd S |
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233 Old Mill Bottom Rd SAnnapolis, MD$3,500
Vacation Rentals, Unknown
Fantastic opportunity to rent a renovated 1931 home located in Annapolis - tucked away in the woods providing 100% privacy. The open-concept kitchen has plenty of natural light with SS GE...... |
1194 Ramblewood Dr |
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1194 Ramblewood DrAnnapolis, MD$3,495
Vacation Rentals, Unknown
Updated 4 Bedroom + office, 3 bathroom split foyer single-family home in the water privileged community of Cape St Claire. Updated kitchen with granite countertops breakfast island and open plan...... |
Harness Creek Rd |
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Harness Creek RdAnnapolis, MD$500
Vacation Rentals, Unknown
This apartment is located on the first floor with a balcony and terrace in a new building. It is simple, cosy, modern, and bright. Entering the house you can find an open kitchen with all...... |