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.
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...... |
979 Dogwood Tree Dr |
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979 Dogwood Tree DrAnnapolis, MD$4,000
Vacation Rentals, Unknown
Welcome home to this charming 4 bedroom, 2 bathroom single family property in Annapolis! Built in 1972, this cozy home features hardwood floors, a fireplace, and modern amenities including a...... |
978 Dogwood Tree Dr |
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978 Dogwood Tree DrAnnapolis, MD$2,400
Vacation Rentals, Unknown
This rancher is located in a spirited waterfront community, Cape St Claire, that includes beaches, playgrounds and schools.The one-floor home features all appliances, generous attic storage and two...... |
624 Tayman Dr |
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624 Tayman DrAnnapolis, MD$5,250
Vacation Rentals, Unknown
Welcome HOME IN SOUGHT-AFTER HILLSMERE! Get ready to fall in love with this 4 bedroom, 3 full bath Annapolis home, just 1 block from the community beach. Enjoy a cup of coffee on your welcoming...... |
1247 Ramblewood Dr |
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1247 Ramblewood DrAnnapolis, MD$3,500
Vacation Rentals, Unknown
Discover the perfect blend of modern comfort and outdoor adventure in this beautifully renovated Cape St. Claire gem, a stone's throw from Broadneck High School. Introducing a recently updated...... |
61 Shaw St |
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61 Shaw StAnnapolis, MD$2,650
Vacation Rentals, Unknown
Annapolis townhome Freshly painted, new appliances . 3 bedroom 2.5 bath Available March 15, 2024... |
1158 Green Holly Dr |
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1158 Green Holly DrAnnapolis, MD$2,500
Vacation Rentals, Unknown
Single family home located in the family friendly neighborhood of Cape St. Claire. Nestled in a quiet cul-de-sac, there is little to no traffic and very quiet. With 2 bedrooms, 1 bathroom and an...... |
501 Harbor Dr |
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501 Harbor DrAnnapolis, MD$3,950
Vacation Rentals, Unknown
Fantastic four-bedroom, three-bathroom cape cod style single-family home with a private driveway and oversized garage in the water-privileged Hillsmere community of Annapolis. Spacious living room...... |
403 Merryman Rd |
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403 Merryman RdAnnapolis, MD$4,500
Vacation Rentals, Unknown
Large Colonial located in the sought-after community of Heritage right here in Annapolis! Prime location backing to woods situated next to community open space with pool/clubhouse beyond! Renovated...... |
1193 Bayview Vis |
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1193 Bayview VisAnnapolis, MD$3,000
Vacation Rentals, Unknown
Welcome to Bayview Vista, located in the coveted Cape St. Claire community. This 4 bedroom, 2.5 bath home is painted a neutral grey tone and the carpeting is almost brand new. The main level is an...... |
501 Knollwood Dr |
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501 Knollwood DrAnnapolis, MD$1,300
Vacation Rentals, Unknown
Newly renovated 1 bedroom, 1 bath lower level with seperate entrance single family house in Rolling Knolls.... |
1217 Tyler Ave |
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1217 Tyler AveAnnapolis, MD$2,400
Vacation Rentals, Unknown
This home is located in the middle of Annapolis City. This charming 3 BR, 1.5 BA home has all new flooring and carpeting, freshly painted, and the bathroom(s) recently renovated. The kitchen is...... |
Friar Trl |
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Friar TrlAnnapolis, MD$2,800
Vacation Rentals, Unknown
Charming furnished cape cod cottage available for summer months or longer. Located in lovely gated waterfront community of Epping Forest on the Severn River. Private beach, clubhouse, tennis courts...... |
1406 Regent St |
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1406 Regent StAnnapolis, MD$3,295
Vacation Rentals, Unknown
Fantastic three-bed, 2.5-bath single-family home with an attached one-car garage and fully fenced backyard in the Knightsbridge community of Annapolis. The main living area has a spacious living...... |
216 Cape Saint John Rd |
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216 Cape Saint John RdAnnapolis, MD$5,000
Vacation Rentals, Unknown
Absolutely beautiful custom-built home located in Cape Saint John. The home features nearly 3300 sq/ft of living. 3 bedrooms, 3 full bathrooms, situated in the back of the neighborhood with views...... |
1942 Fairfax Rd |
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1942 Fairfax RdAnnapolis, MD$3,395
Vacation Rentals, Unknown
Modern three-bedroom, two-bathroom single-family home in Annapolis with a large, fully fenced backyard. The main living area has a beautiful kitchen with granite counters, stainless steel...... |
731 Rosedale St |
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731 Rosedale StAnnapolis, MD$2,695
Vacation Rentals, Unknown
Great 3 bedroom, 2.5 bath single-family home in Cedar Park community, close to the Navy Stadium and downtown Annapolis. Features spacious living and dining areas, a large back yard and deck, eat-in...... |
17533 Dunton Rd |
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17533 Dunton RdAnnapolis, MD$1,750
Vacation Rentals, Unknown
This gorgeous one bedroom, one bathroom apartment on the outskirts of Annapolis must be seen to be believed. Monthly rental rate includes all utilities, cable TV and high speed internet access....... |
55 Pinkney St |
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55 Pinkney StAnnapolis, MD$1,800
Vacation Rentals, Unknown
Charming little home located in Downtown Annapolis. This two bedroom home is perfect for small families or couples! - stackable washer/dryer - fully loaded kitchen including fridge, stove/oven,...... |
1294 Virginia St |
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1294 Virginia StAnnapolis, MD$4,600
Vacation Rentals, Unknown
Absolutely BEAUTIFUL, custom Traynor built, craftsman home! Open concept with tall ceilings and loads of character. The home features 5 bedrooms, 3 full baths, a finished basement, granite counter...... |
689 Genessee St |
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689 Genessee StAnnapolis, MD$3,300
Vacation Rentals, Unknown
Great home in a family-friendly neighborhood zoned to the best elementary school around, West Annapolis Elementary! 3 bedrooms upstairs, 4 bathrooms and a fully finished basement with a...... |
815 Cedar Park Rd |
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815 Cedar Park RdAnnapolis, MD$2,500
Vacation Rentals, Unknown
3 BR/ 2 BA Dutch Colonial - Location. Location, Location. Germantown-Homewood neighborhood in the City of Annapolis. Easy walking distance to the Naval Academy and Historic Downtown/City Dock....... |
7 Steele Ave |
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7 Steele AveAnnapolis, MD$3,500
Vacation Rentals, Unknown
Tenant Occupied 24 hour Notice of ALL showings Prime Rental in Excellent Murray Hill Location. This 3 Bedroom Cape Cod features an updated kitchen with Stainless Steel Appliances, updated main...... |
2615 Compass Dr |
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2615 Compass DrAnnapolis, MD$2,395
Vacation Rentals, Unknown
Great two-bedroom, 2 bathroom home with an attached garage in the 55+ community of Heritage Harbour in Annapolis. Perfectly located in the community, close to all the amenities, yet away from the...... |
1199 Highview Dr |
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1199 Highview DrAnnapolis, MD$1,200
Vacation Rentals, Unknown
Couple seeking an individual or another couple to share a home in Cape St. Claire, Annapolis, MD. The home is equipped with a sunroom, deck, shed, washer & dryer, fenced in backyard, hot tub, level...... |
1610 Laurel Ln |
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1610 Laurel LnAnnapolis, MD$7,000
Vacation Rentals, Unknown
Spectacular Annapolis Waterfront Home in Amberley Community. This beautifully renovated 3 level home features 4 bedroom (2 master bedroom suites) 3 1/2 baths. Gourmet kitchen with gas cooking,...... |
919 Windsor Ave |
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919 Windsor AveAnnapolis, MD$2,800
Vacation Rentals, Unknown
This is a cozy 3 bedroom, 2.5 bath single family home in the sought-after Eastport community. This home has hardwood floors, extra storage space, and a lovely front porch. It also has a deck and a...... |
Windsor Ave |
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Windsor AveAnnapolis, MD$2,800
Vacation Rentals, Unknown
This is a cozy 3 bedroom, 2.5 bath single family home in the sought-after Eastport community. This home has hardwood floors, extra storage space, and a lovely front porch. It also has a deck and a...... |
59 Sleepy Hollow Rd |
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59 Sleepy Hollow RdAnnapolis, MD$3,595
Vacation Rentals, Unknown
Great four-bedroom, three-bathroom, split-level home in the water-privileged Lindamoor on the Severn community of Annapolis. Spacious open-plan living area, dining room, and kitchen with access to...... |
1096 Magothy Cir |
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1096 Magothy CirAnnapolis, MD$1,650
Vacation Rentals, Unknown
Completely renovated waterfront home with private 2nd floor bedroom with cathedral knotty pine ceilings, fan, expansive views of the bay, 18' x 20' room large closet, TV with cable, Verizon FiOS,...... |
1118 Bay Ridge Ave |
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1118 Bay Ridge AveAnnapolis, MD$2,900
Vacation Rentals, Unknown
OPEN HOUSE: Sunday 2/11 10:00AM - 12:00PM Adorable Eastport Cottage available immediately. Hardwood floors and open kitchen. Amazing natural light in open living space with skylights. Energy...... |
328 Edgemere Dr |
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328 Edgemere DrAnnapolis, MD$3,500
Vacation Rentals, Unknown
Large 4-bedroom 2-bath rancher/rambler in the highly desirable water-oriented community of Hillsmere! The community of Hillsmere offers countless amenities such as a community beach with panoramic...... |
1934 Carrollton Rd |
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1934 Carrollton RdAnnapolis, MD$4,300
Vacation Rentals, Unknown
Tours available starting March 1st. Beautifully updated mid-century modern home is found just over the Naval Academy Bridge in the highly sought after neighborhood of Pendennis Mount. Among the...... |
207 Ash Ln |
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207 Ash LnAnnapolis, MD$2,850
Vacation Rentals, Unknown
Enjoy over 1/2 an acre property for ultimate relaxation. Open the windows to hear the birds chirping in the morning, or sit under the tree in your hammock. Take your dog on a 1/2 mile walk down to...... |
321 Hillsmere Dr |
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321 Hillsmere DrAnnapolis, MD$3,450
Vacation Rentals, Unknown
Recently renovated home in hillsmere estates with access to private community beach and park. In a great neighborhood and kids friendly community. Close to downtown, bayridge shopping center and...... |
7 Mizzen Ct |
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7 Mizzen CtAnnapolis, MD$2,450
Vacation Rentals, Unknown
COMING SOON! Great townhouse with 2 master suites! Newer flooring. Wood burning fireplace with patio out back. Close to Eastport and Downtown Annapolis! Community Pool. Smaller pets considered case...... |