308 properties available

Located in Annapolis, Washington, United States. 3-story, dog-friendly home near beaches with home theatre, grill & gaming tables Bella ChateauOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located just a block away from the Chesapeake Bay and Bay Ridge community beaches and a few miles from Annapolis' historic downtown area, this roomy home will be perfect for a memorable family vacation! There are warm and inviting social rooms for gathering, quiet nooks for some me-time, and sprawling outdoor spaces. The large deck overlooking the lawn into a wooded area offers a very private and serene setting. A sizeable outdoor table with seating and a gas grill is perfect for warm-weather barbecues and meals alfresco.The spacious living room is adjacent and open to the kitchen with big, comfy furnishings. The sitting area off of the kitchen has more comfortable furnishings and a big-screen TV. The inviting den has leather furnishings and a TV. The open and

Located in Annapolis, Washington, United States. Beautiful Victorian in Great Eastport Location Available for Annapolis Boat Shows. Large historic Victorian in desirable Eastport, close to restaurants and short walk over Spa Creek Bridge to downtown. Sleeps 8, off street parking for 4 cars with unlimited street parking. 3 bedrooms (1 King, 2 Queen), 2 1/2 baths plus convertible office with Queen Murphy bed. Gorgeous inside and out, open floor plan, every amenity including 3 wide screen tvs, kitchen updated in 2021 offers Subzero fridge, Viking range, Gaggenau double ovens, 2 Fisher Paykel double drawer dishwashers. Beautifully manicured fenced yard with 2 Weber grills (gas and charcoal), table seats 8, plus deck seating! Available for Commissioning Week 2024 and 2025. Also available for other Academy events: $800 per night, 3 night minimum, 2024 Commissioning Week $9800 .

Located in Annapolis, Washington, United States. Historic house in Annapolis Arts District Super host house rental in charming historic house, private and upscale, tucked away in the quiet President’s Hill neighborhood, located off West Street (Annapolis Arts District) where many restaurants and shops are located. City Dock and the Navy Stadium within walking distance. Free shuttle bus to downtown. Enjoy entire house, including front porch and back yard garden. Fully stocked for cooking including all basics (spices, oil/vinegar), coffee/tea.Upscale, cozy, and large spaces. Large king sized bed with excellent quality mattress in master bedroom. Excellent quality Queen sized mattress and bed in second bedroom. There is a large TV in the front living room area. A wonderful wooden front porch with Adirondack chairs, a yard with patio furniture to lounge around on. Master bath has a deep bathtub for soaking and shower.Guests have the entire house, except attic space.Other things to note:There is a reading/work area with desk on second flo

Located in Annapolis, Washington, United States. Craftsman Home in Annapolis Waterfront Suburb Beautiful, family-friendly home in St. Margaret's area of Annapolis. Only a few miles from downtown, the stadium and all Annapolis has to offer. Enjoy a beautiful kitchen, open concept living/dining room that opens to a lovely deck, patio and backyard. Relax in a gorgeous master suite.

Located in Annapolis, Washington, United States. Bright and cheery home. Just a short 2 blocks from the beach. RENT-001177-2024 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A TEAM MEMBER WITH ADDITIONAL INSTRUCTIONS FOR BOOKING.This Corner Condo has a great water view above the Eastport Yacht Club. Two (2) bedrooms and two (2) full bathrooms in Eastport with a maximum occupancy of 3. 2 reserved parking spots in the garage. 1 Queen and 1 futon in study. . Features include fully equipped kitchen with granite countertops, stainless steel appliances, microwave, dishwasher, regular/drip coffee maker, full size washer/dryer, and air conditioning. Walk to all the cool restaurants and pubs in Eastport or downtown. Walk to the City Dock for Band Concerts every Tuesday in the summer and walk to the Eastport drawbridge every Wednesday in the summer to watch the finish of the Wed. night Sailboat races. REN - 143722

Located in Annapolis, Washington, United States. Cozy family-home in the woods, 10 min to Naval Academy! Embed yourself in the quietness of the woods and birds singing. Our backyard has the 5th largest tree of its species in MD and takes out whole backyard beyond the deck. Safe and friendly neighborhood, our 3-floor Brazilian-American artsy family home offers in the main floor: powder-room, kitchen, dining, living and family rooms. Top floor with access to 1 master bedroom suite and 1 of the other 2 bedrooms and a social bathroom. The third bedroom is downstairs in the basement. We love having guests and sharing our lovely space to inspire you to reconnect with the magic of who you truly are. We love being immersed in nature, and taking a morning and/or evening walk in the woods to view the Chesapeake Bay water along the 2.2 mile pathway. There are two bird observatories where you can stop to enjoy the Marshall areas and the Bay view or meditate. During your stay, if you are interested in booking a whole health and healing therapy

Located in Annapolis, Washington, United States. Beautiful 4BR Waterfront Home in Historic Downtown Annapolis - Close Proximity to Everything! THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A TEAM MEMBER WITH ADDITIONAL INSTRUCTIONS FOR BOOKING.BEAUTIFUL home in walking distance to the Academy and City Dock! Enjoy this waterfront home with breathtaking views of the sunrise and sunset! Home includes an updated, rustic gourmet kitchen with a dining area and sun room that holds up to 6 guests. Perfect for entertaining for Commissioning Week or a place to relax during the rush of Boat Show! 4 Bedrooms, 2.5 Bath - ample space for you and your family to spend, kick back and enjoy the Annapolis Charm! Home has 2 kayaks and 1 paddle board open for guest use! Please note: Homeowner has a cat. Call Annapolis Accommodations for more details! Please note, this is an owner occupied home outside of rentals. We ask that you respect any closets/areas of the home that are identi

Located in Annapolis, Washington, United States. Calico Cottage Guest House Cute-as-a-bugs ear West Annapolis guest cottage. In settled neighborhood just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8.Park 10 feet from your front door. There's only 1 step to enter. No stairs to negotiate while carrying luggage! Parking's plentiful.15 minute walk to the Weems Creek drawbridge with scenic, serene waterviews. A few more minutes and you're at the charming boutiques of West Annapolis and local coffee shop Bean Rush Cafe.The space:Cottage features a bedroom/sitting room, kitchen/dining area and bathroom with shower.High-speed internet, 42" flat screenTV with fios cable. Kitchen equipped with two-burner cooktop, mini-fridge, and microwave.Stacked washer and dryer for your convenience.Attached deck with wrought iron patio table and umbrella.NOTE: The house is located next to Route 50. There is a sound wall but you will hear moderate road noise inside and more outside. Cottage is equipped with a soothing spa sound

Located in Annapolis, Washington, United States. 3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace Ensign's RidgeOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perfect for family and group gatherings, this darling, three-story home near Severn River is calling your name! There is a beautiful paver patio with a backyard firepit surrounded by a wooded backyard and mature landscaping. Planning on hosting warm-weather barbecues? There is a propane grill available for you! The screened porch off the kitchen (main level) features an outdoor dining table for six overlooking the backyard.Inside, the beautifully decorated open floor plan is perfect for entertaining and family gatherings. The comfortable family room adjoining the kitchen offers a smart TV, a large sectional sofa, two big and cozy chairs, and a wood-burning fireplace. The formal living room has inviting and comfortable conversational seating. When mealtime com

Located in Annapolis, Washington, United States. Elegant Boutique Hotel Near Maryland State House - Short Walk Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine at local restaurants - all from walkable distance!Imagine stepping into a story, where charm and modernity blend seamlessly under the roof of history. Our inviting sanctuary marries the elegance of the 18th century with today's comfort, in three different buildings, each one nestled in the heart of Annapolis. With breathtaking views, a stone's throw from iconic landmarks and exquisite dining, we're more than just a stay; we're an experience. Revel in the opulence of time travel, coupled with the conveniences you love, all waiting to welcome you.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- This Room is located in Governor Calvert House- The property requires a damage deposit of $100 /night/unit on the

Located in Annapolis, Washington, United States. Bay Ridge house by Quiet Waters Park, Thomas Point Park Brand new home with comfortable beds, open floor plan with kitchen excellent for entertaining, and fully equipped. All furniture is brand new. Located on quiet dead end street with large yard. A 5-minute walk to Quiet Waters Park, Hillsmere shopping center with restaurants (such as Annapolis Smokehouse and Grumps Cafe), the Dark Horse Bar, and Giant. A 10-minute drive to downtown Annapolis. Also nearby is Thomas Point Park. Ideal for boaters mooring at Bembe Beach Rd Yacht clubs or visiting family at Bay Woods Assisting Living or Naval Academy. Comfortable getaway at a much better value than hotels!The home is brand new built in 2023, on a quiet private residential lot. Living space is on the second floor, reached by an outside staircase. The front door opens into an open floor plan kitchen and living room excellent for entertaining. The living room has a chair that folds out to a single sized bed. The couches recline, have phone

Located in Annapolis, Washington, United States. Home with EV charger and garage parking!!Downtown Fleet Street Carriage House. Friends! We are a USNA family (‘92) that loves this town! Walk to bottom of our street and you are at the docks. Walk to the top and you are at State Circle…and the GARAGE!! Now with EV! Although this blue Carriage House is from the 1800's, u will love all the modern touches including bluetooth speaker, smart tv, recessed lighting, new kitchen appliances, Nest thermostat and remodeled kitchen and bathrooms. This is a brand new short term rental listing and we hope you enjoy it.STR22-145194The spaceMaster Bedroom- Brand new king bed with Novaform mattress. Sconce lights for bedroom readers. New fan with remote and attached full remodeled bathroom.Bedroom 2 - Queen homemade bed with new Novaform too. Everyone says how comfortable it is.Pullout Couch - new and queen.Please inquire if you plan to park in the garage. It is very small and the wall is not straight. My car is 75"x186" and it is very very snug. Pleas

Located in Annapolis, Washington, United States. Classic Victorian home in the heart of Eastport 3 bedroom house with off street parking, friendly porch. Make yourself at home and enjoy the neighborhood! There’s a beach two blocks down Chesapeake Avenue and the Maritime Museum on 2nd Street. Indeed, there is a place to rest and enjoy the water views at the end of almost every street on the peninsula, it’s a great walking neighborhood, just 1 mile to historic Annapolis and the Naval Academy. Closer still are authentic restaurants, like Davis’ Pub and the Boatyard, and a shopping area for ribs, pizza, fresh fruit, liquor, a bakery and more. The water taxi to downtown and elsewhere is two blocks away on 2nd Street at the Chart House. The house opens to a sitting room at the entry, adjoining a dining area (set for 8) and a living room with TV, a gas fireplace and access to backyard. There’s a bright, functional kitchen with appliances and a nice view of the fenced backyard with BBQ and fire pit. Upstairs there is one bedroom with

Located in Annapolis, Washington, United States. West Annapolis Hidden Gem

Located in Annapolis, Washington, United States. 5 BDRM across from the USNA Stadium Across the street from the Naval Academy Stadium. Open floor plan with stainless steel appliances, two islands, 8-10 person dining table, 3-sided fireplace & family room. Bedroom & full bath on the first floor. 4 bedrooms upstairs each with their own bathroom. Upstairs family room with large sectional tv area. Driveway has room for 2 cars and street parking permitted. Beautiful backyard outdoor seating area with comfy couches fire pit. Screened in porch with family dining table.

Located in Annapolis, Washington, United States. Beautifully Furnished Home, Steps to USNA Stadium, Walk to Downtown Annapolis! This 3 BR/3 Bath home is literally steps from the USNA Stadium (graduation) and within walking distance of downtown Annapolis. Fully furnished with beautiful antiques, rugs, etc., this centrally located house is the perfect place to rest and/or entertain while exploring the best of Annapolis. The dining table can expand to seat up to 6 (8 with a squeeze). There are 2 outdoor dining areas, fire pit, back deck, and front porch. Kitchen features gas stove, Le Creuset equipment, etc. The two smaller bedrooms each have a twin bed. The master bedroom has an antique double bed. The basement features two rather plush cots, allowing you to sleep as many as 6 people. We ask that all guests be respectful of the furnishings, as antiques must be treated with care.

Located in Annapolis, Washington, United States. Elegant Stay Perfect for Exploring Annapolis' Shops and Boutiques. Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine at local restaurants - all from walkable distance!Historic Inns of Annapolis features accommodations across three distinct buildings: Maryland Inn, Governor Calvert House, and Robert Johnson House. Please note, that all guests will check in at Governor Calvert House, the address displayed on the listing.- This Room is located in Robert Johnson HousePLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of $100 /night/unit on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon arrival.- Following property rules, the minimum age required for check-in is 21 years ol

Located in Annapolis, Washington, United States. Private Eastport Guest Suite in Annapolis Enjoy a clean, comfortable and private suite in the heart of Eastport. Steps away from Davis' Pub and Forward Brewing as well as Annapolis's finest restaurants, fun shops and marinas with off-street parking. Quick walk to historic Annapolis and the Naval Academy. Park your car and enjoy what Annapolis has top offer on foot!

Located in Annapolis, Washington, United States. Walk Everywhere! Your Ultimate Annapolis Retreat on Horn Point Escape to your ideal rental property at 125 Chester Avenue, located in the desirable neighborhood of Horn Point in Annapolis, MD. Experience the authentic charm of Annapolis living in this well-appointed residence, offering a perfect blend of comfort and convenience.Situated two blocks from the picturesque Chesapeake Bay, this home provides easy access to water activities and stunning views. Walk and explore both the charming "Maritime Republic of Eastport" and the vibrant and historic downtown Annapolis area, each brimming with unique shops, delightful dining options, and lively entertainment. Immerse yourself in the city's rich naval history by visiting the United States Naval Academy (it's truly an ideal rental for Commissioning Week!) or take a ghost tour of the colonial city's haunted locales.Step inside 125 Chester Avenue and discover a welcoming space that exudes a warm and inviting atmosphere. The thoughtfully desig

Located in Annapolis, Washington, United States. Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard Base Camp on the LakeOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'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 perfect choice for your next family adventure.Lovely landscaping, a luscious green lawn, a bubbly hot tub, an outdoor Ping-Pong table, a firepit surrounded by colorful Adirondack chairs, a private dock (6.5+ depth), a gas grill, and a variety of outdoor spaces for lounging and entertainment await! Fish and crab off the dock, explore the Chesapeake Bay Foundation Trail and two miles of community beaches, or tr

Located in Annapolis, Washington, United States. One block from USNA Gate 1, or 3 blocks from City Dock, this attractive home is close to the center of the universe! THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A TEAM MEMBER WITH ADDITIONAL INSTRUCTIONS FOR BOOKING.One block from USNA Gate 1, or 3 blocks from City Dock, this attractive home is close to the center of the universe! Nicely furnished, with a large collection of European clocks (which can be turned off during your stay if you wish), The house sleeps 7 comfortably in 4 beds (queen, double, 2 twins) and a twin sleep sofa. Small yard, parking permits available. This is a NON-smoking house, indoors and outdoors. Distance from USNA: 4 Minute Walk Distance from City Dock: 4 Minute WalkMaximum to Sleep: 7 Bedroom 1: Queen Bedroom 2: Double Bedroom 3: Twin Beds

Located in Annapolis, Washington, United States. Gorgeous House in the Heart of Annapolis, Walk to Everything! Located within walking distance of everything Annapolis has to offer, this 3BR/2.5 Bath historic Craftsman home is beautifully furnished with a mixture of antiques and comfy modern furniture. Walk to: Downtown Annapolis, USNA, Navy Football Stadium, and all of the wonderful bars, restaurants, and shopping, including: Paul's Cafe, Lemongrass, Sailor Oyster Bar, Preserve, Chick & Ruth's, Choptank, Ram's Head, Miss Shirley's, etc. USNA - less than 2 miles awayFootball Stadium - steps (about 200 feet) awayChoptank - 1.6 milesMiss Shirley's - less than 1 mileSailor Oyster Bar - less than 1 milePaul's Cafe - less than half a mile

Located in Annapolis, Washington, United States. This Eastport condo has a large deck with amazing views of Spa Creek and downtown Annapolis. REN - 144911 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A TEAM MEMBER WITH ADDITIONAL INSTRUCTIONS FOR BOOKING.Amazing Views of everything in Annapolis. This Eastport condo has a large deck with amazing views of Spa Creek and downtown Annapolis. Enjoy the community pool in the summer and being within walking distance to all the wonderful downtown & Eastport restaurants and shops. This place comes with one reserved parking spot, a huge bonus for being so close to historic Annapolis. There is a washer and dryer in unit, a great added amenity in this building! There are 2 bedrooms with Queen in Master and 2 twins in 2nd bedroom. The interior was completely updated in 2018 to give you a fresh, clean condo! Call Long and Foster today to set up your showing!This building does not have an elevator. REN-144911

Located in Annapolis, Washington, United States. Gorgeous renovation in HistoricDistrict -New listing ! Welcome to our newest listing in Downtown Annapolis. Brand new renovation with a nautical flair this is the perfect spot for your next trip to town. We sleep six very easily with three bedrooms and plenty of extra space - not only a formal living room but a family room and large screened in back and front porch . This house is spotless with beautiful furnishings and will satisfy the most discerning travelers . Walk to everything Annapolis has to offer from our convenient location or take the water taxi that picks up at the end of the street . One parking pass provided . C week and boat shows for 2019 are booked.