Annapolis, Maryland


Properties Available 45 properties available
Located in the highly-desirable Murray Hill neighborhood in Annapolis, find this well-appointed house. Boasting great walkability to the area's restaurants, art galleries, shops, parks, and water taxi - fun in the sun is inevitable! On days you don't want to go far from your stay, sit and enjoy the pleasant Maryland weather from the sprawling deck
Seas The Bay (579378)
Annapolis, MD
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
This gorgeous five bedroom home boasts a screened porch, great interiors, and a guests house. Inside, there are many areas to escape to or gather in. A warm formal living room has a fireplace and comfy seating. The French doors open onto a large screenedin porch overlooking the pool. The huge lower level recreation room has a sectional and anothe
The Liberty Club (290828)
Annapolis, MD
House
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Overlooking Spa Creek, this updated Annapolis condo is perfectly located amidst the city's vibrant entertainment hub. Known for its delicious seafood, sailing, and shopping - there's something for everyone! Attractions like the U.S. Naval Academy Museum, Quiet Waters Park, William Paca House & Garden, Sparrows Beach, and numerous marinas are all wi
USNA Getaway (594693)
Annapolis, MD
House
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 6 guests
Experience incredible and memorable indoor and outdoor spaces at this spacious waterfront home! Admire unparalleled Lake Ogleton views from your large backyard, which also is equipped with a fantastic dock (6.5+ depth), private hot tub, deck, and a screened porch ready for family game night and crab feasts! Private and comfortable, this home is the
Base Camp on the Lake (290403)
Annapolis, MD
House Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 16 guests
Experience a getaway like no other at this fantastic waterfront home located on the shores of Severn River with 70 feet of open water frontage! Watersports enthusiasts will have a blast here - this home features a private dock where guests can tie up their boats and launch the provided two-person kayak or any of the two stand-up paddleboards. There
Taids Inn (580073)
Crownsville, MD
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Find gorgeous gathering spaces inside and out at this light-filled three-story waterfront home on a protected inlet of the Chesapeake Bay. Here in Bay Ridge, you'll have a private dock, access to the bay beaches, and a stunning setting for family vacations and special holidays. You'll be within five miles of historic downtown Annapolis, home to cha
Annapolis Bay Ridge Retreat (579413)
Annapolis, MD
House
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
This historic home is close to downtown and the stadium, and offers the best location to view the Blue Angels air show! Its conveniently located in the West Annapolis waterfront community and boasts acres of lawn, a dock, a beach, and a beach house. Its surroundings will make for an unforgettable stay on the Severn River. There are many areas to e
Severn River Osprey Cottage (290135)
Annapolis, MD
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
This delightful beach house offers vintage charm and a convenient location within a block of Edgewater Park and is just a short walk from community beach areas and water access. Despite the authentic appeal, the home has been lovingly updated and maintained for complete modern comfort, making this a great choice for a family getaway. The Londontown
Pine Whiff Beach House (582449)
Edgewater, MD
House
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Nestled right on Severn River's shoreline, this waterfront retreat has been completely remodeled, redecorated, and boasts gorgeous views from both floors! Right at your stay, utilize the kayak and paddle board for peaceful dips into the water, or rent a boat and tie it up to the private pier - ready for your effortless use. Mere minutes away from y
Valentine Creek Retreat (577521)
Crownsville, MD
House
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Located within a block of the William Paca House and Gardens and two blocks from Annapolis Harbor, St. Johns College, and the Naval Academy, this historic home is the perfect home base for an exciting and memorable trip to Annapolis! This retreat was built in 1900 and renovated in 2018 with all new furniture (2019). The enclosed and private patio o
Anchors Aweigh (291093)
Annapolis, MD
House
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Nestled into the coastline of Lake Ogleton off of the Chesapeake, this five-bedroom waterfront home with a pool, spa, and private pier features walls of windows and newly renovated interior and exterior spaces to enjoy your coffee during the sunrise. You are only five miles from historic downtown Annapolis and the US Naval Academy. Swim, boat, padd
The Morning Watch (290454)
Annapolis, MD
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
This newly renovated townhouse with a large backyard is the perfect place for your getaway. Each of the four spacious bedrooms has been beautifully outfitted with your comfort in mind. The open floor plan provides great gathering space with comfy seating and a smart TV, making it the perfect living room space for an afternoon nap or group movie nig
The Herons Nest (290144)
Annapolis, MD
House
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 11 guests

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