Vacation Rentals By Owner In Annapolis, MD

Escape to The Yellow Annapolis Cottage: A Chesapeake Getaway with Stunning Bay ViewsbrbrbrWelcome to our Bay Ridge Yellow Cottage with views of the Chesapeake Bay and steps away from the many Beaches Bay Ridge has to offer. This is a perfect destination if you’re in town visiting the Naval academy (15 min drive), for a wedding, couples trip, a family vacation on the Bay & everything in between. brbrThe Space:brbrThis 1920’s Bay Ridge cottage features 3 bedrooms and 2 full bathrooms. brDownstairs has two bedrooms, one with a king and two closets and a smaller bedroom with a queen with views to the bay from bed. Upstairs, there is a full bathroom and additional bedroom with a queen bed and plentiful views. brbrThe home’s open-concept kitchen flows effortlessly into the living room, which features large windows that bathe the space in natural light and provide sweeping views of the bay. The spacious dining room can comfortably seat 8.brbrbrOutdoor Living:brbrStep through four glass doors onto the inviting back porch, where you’ll find a grill, a dining table that comfortably seats six, and the perfect chairs for enjoying a peaceful sunrise with a cup of coffee in hand. It's the ideal spot to watch local crabbers bring in their morning catch. We love spending time out here—enjoying crab feasts with family and friends, then cooling off with a refreshing dip in the bay. The deck offers breathtaking views of the Chesapeake, making it feel like an everyday vay-cay!brbrbrWe want you to have the best possible stay while booking our Yellow Bay Ridge Cottage but want to remind our guests that it is an updated 1920’s cottage so it does need to be cared for with love and we ask that you treat our home as you would your very own. No parties, large gatherings or events can take place during your stay- in respect to our neighbors and the cottage’s old pipes! Additionally, we are here to answer any questions you may have about the cottage, rules, Annapolis/Bay Ridge, things to do, restaurant recs. Want to hire a private chef for the evening Please inquire! If you need to Amazon anything before your stay- we can accommodate- just reach out with any personal requests and we’d be happy to assist! brbrbrFavorite Things to Do in Beautiful Bay Ridge:brbrWalk to the bluff to catch an unforgettable sunset or take a peaceful stroll below the bluff along the bay.brExplore the neighborhood’s beaches—perfect for lounging, swimming, or relaxing in the sand.brCrab and fish off the jetties at the beach for a fun, authentic experience.brThe Bay Ridge Marina offers pickleball (bring your own net), a basketball court, and a playground, all with views of Lake Ogleton—ideal for a day of outdoor fun.brFor nature lovers, explore the trails behind the Chesapeake Bay Foundation on Herndon, where you can hike through the woods and enjoy peaceful surroundings.brbrWhether you're here to explore Annapolis, spend time on the water, or simply relax in a serene setting, The Yellow Annapolis Cottage offers the perfect location for an unforgettable escape.

Cottage

Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach

Annapolis, Maryland, United States

3

Bed

Bath

6

Sleeps

$538.24

The property is all set up for boating and fishing with a drive-thru driveway. It is located one block from the boat ramp and has a private crabbing and fishing pier across the street. The community fishing pier at the end of the street offers a view of Thomas Point Lighthouse. The house has an open floor plan with a nice screened-in porch and a large second-story balcony with a water view.

Sunny and spacious water view/access home in Annapolis.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$591.63

Step into a truly exceptional condo nestled in a beautifully preserved historic church, just 2 blocks from the U.S. Naval Academy Gate 3, and walking distance to Maryland Avenue and downtown shops, delicious restaurants, and scenic waterfront.brWith its beautiful décor and inviting atmosphere, this condo will quickly become a place you’ll want to re-book for every Annapolis visit.brbrThis is a space like no other:brThis beautifully condo preserves stunning original architectural features while offering all the comforts of upscale living.brTwo-story stained glass window flooding the living room with lightbrExposed original brick throughout several roomsbrFormer church bell tower thoughtfully converted into a private study/wine room with panoramic views of AnnapolisbrOpen-concept layout with the kitchen perfectly centered between the living and dining areasbrUnique wet bar, ideal for entertaining or relaxing after a day of exploringbrbrKitchen & Living:brThe full kitchen features custom cabinetry and upscale stainless steel appliances, perfect for everything from quick breakfasts to elegant dinners. The open design makes the space feel bright, inviting, and ideal for gathering.brbrBedrooms & Baths:brKing bedroom with full bathbrQueen bedroom with full bathbrAdditional powder room for conveniencebrComfortable, quiet, and thoughtfully appointed for a restful stay.brbrUnbeatable Location!brStep outside and you’re immersed in the best of Annapolis:br2 blocks to the U.S. Naval Academy (Gate 3)brWalk down charming Maryland Avenue to coffee shops, restaurants, furniture, and antique storesbr2 blocks to the State House and Governor’s MansionbrShort stroll to Main Street and the Annapolis waterfront, with its shops, dining, and harbor viewsbrbrA car is not needed to explore everything on foot.brbrThis condo is perfect for:brbrNaval Academy visits and eventsbrHistory lovers and architecture enthusiastsbrGuests seeking a distinctive, upscale Annapolis experiencebrbrGood to Know:brbrEntire condo is private for your staybrNon-smokingbrNo parties or eventsbrbrIf you’re looking for a stay that combines history, elegance, and the best location in Annapolis, this Parish House condo is truly unmatched.

Historic Parish House 2-Bedroom Condo Steps to Naval Academy

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$703.15

Summary:brbrDiscover 'The Crabby Patty,' a spacious 3-BR, 2.5-BA home in the heart of downtown Annapolis. Blending modern comfort with historic charm, this stylish retreat is perfect for families or groups. Enjoy a fully equipped kitchen, a dedicated workspace, and a prime location just steps from the US Naval Academy and city waterfront. Walk to everything from this unforgettable getaway.brbrbrbrThe Space:brbrWelcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history and vibrant culture of this charming city. brbrOur inviting 3-bedroom, 2.5-bathroom home is a spacious retreat, thoughtfully designed to provide an unforgettable vacation experience. The open-concept living area invites you to relax, filled with stylish furnishings and ample natural light.brbrbrbrPrepare meals in the fully equipped kitchen, complete with modern stainless steel appliances, before gathering around the large wooden dining table. After a day of exploration, rest and recharge in our comfortable bedrooms.brbrbrbrWhere you will sleep: brbrbrbr* Bedroom 1: Features a plush bed for a restful night's sleep.brbr* Bedroom 2: Includes a dedicated desk, creating a perfect workspace if needed.brbr* Bedroom 3: Offers a fun and flexible sleeping arrangement with bunk beds.brbrbrbrThe home includes two contemporary full bathrooms upstairs and a convenient half-bathroom on the main level, all stocked with complimentary toiletries.brbrWasher & dryer in-homebrbrbrbr STR22-145090brbrbrbrGuest Access:brbrYou will have private access to the entire home. For your convenience, we offer seamless self check-in with a smart lock. A washer and dryer are also available for your use during your stay.brbrbrbrThe Neighborhood:brbrHistoric cobblestone sidewalks are a captivating feature found around the neighborhood. Walking on these cobblestone sidewalks is like stepping back in time, as they have been part of the urban landscape for centuries. They add a touch of nostalgia and character to historic districts, enhancing the overall ambiance and charm of the area.brbrbrbrGetting Around:brbrA car is not needed, but there are several parking garages close to the house. Due to a change in city regulations, guest parking passes for the residential street can no longer be provided for your stay. You may park on the street for up to 2 hours in any other open space. brbrbrbrThe city does provide free parking from 6PM Friday to 6AM Monday at the Calvert Street Garage (19 St. Johns Lane) or you can also park in the following garages/lots: Hillman Garage (150 Gorman Ave - entrances from Main St or Duke of Gloucester) South Street Lot - South Street off Church Circle, Gotts Court Parking Garage – (25 Northwest Street) Knighton Parking Garage – (1A Colonial Avenue), Park Place - 5 Park Place (just off West St ). brbrbrbrThe free Annapolis Circulator bus stops at all the city garages/lots and the city dock and can be used to get to/from the garages. Please see the Annapolis Parking website for further detailsbrbrbrbrOther Things to Note:brbr* This home provides a comfortable and stylish haven for your Annapolis adventure. We look forward to hosting you!brbr* City of Annapolis STR License: STR22-145090brbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a seamless self check-in process. While we won't be on-site during your stay, we are always available and happy to assist with any questions or recommendations via the app or phone to ensure you have a wonderful time.

Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$600.4

This Charming Annapolis property features 2 king beds and 2 queen beds; 2 living areas complete with large TVs. The Kitchen is fully equipped with everything you will need to cook a meal and has seating for 14!! Our place will help you feel at home while you're traveling to Annapolis. The property is a 4-minute drive, and a 13-minute walk to the Stadium!

Charming Annapolis Escape!!

Annapolis, Maryland, United States

Bed

Bath

8

Sleeps

$491.77

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrJust minutes from Downtown Annapolis, this charming Cape is located in a quiet water-privileged neighborhood with easy access to the Naval Academy, the Bay Bridge, and highways to Baltimore and Washington D.C. From the minute you enter the 3-bedroom, 2 bath home, you will relish the beautiful private gardens in the spacious fenced-in backyard and furnished patio. brbr brbrThe home is ideal for a large extended family traveling together or 2 families traveling together. The main floor has a bedroom with a Queen bed and full bath in the hall. Spread out in the family room, living room (with remote gas fireplace), dining room and kitchen. Head upstairs to the King bedroom and hangout den that doubles as a bedroom with a Full bed and sofa that pulls out to a Full bed (linens included). The lower level has a full laundry room and exercise room. brbr brbrThe neighborhood amenities include beaches, boat ramp, kayak rack and nature trails. The community park has the most expansive view of the Chesapeake Bay that spans to the Eastern Shore, Annapolis, and the South. brbr brbrSLEEPING ARRANGEMENTS 3 BR/2 BA / Sleeps 7: brbrMain Floor Queen Bedroom: brbr-Queen Bed brbr-Flatscreen TV brbr-Full Bath in the hall with shower/bathtub combo brbr brbrKing bedroom brbr-2nd Floor brbr-King bed brbr-Flatscreen TV brbr-Full EnSuite bath with double vanity and stand-up shower brbr brbrDen brbr-2nd Floor brbr-Full bed and Full sofa sleeper brbr-Flatscreen TV brbr-Full bath in the main floor hall brbr brbrHIGHLIGHTS: brbr-Full kitchen brbr-Dining table seats 6-8 brbr-Propane Grill brbr-Propane remote fireplace brbr-Fire pit on back patio brbr-High Speed Internet and WiFi brbr-Big Screen Smart TVs brbr-Bluetooth Alexa, printer and shredder brbr-Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr-Parking for 2-3 cars in driveway/car port brbr-Full-sized washer & dryer located inside the home brbr-Community beach and park brbr-Dogs and cats allowed with Non-refundable $150 deposit per pet. brbr-Keyless entry. Drive straight to your rental home and enter the side door with a lock code. brbr brbrProperty Distance to: brbr-Downtown Annapolis – 2.5 miles brbr-U.S. Naval Academy – 3 miles brbr-Washington, DC – 33 miles brbr-Baltimore - 32 miles brbr brbr* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. brbr* All beds are made with freshly-laundered sheets & towels brbr brbrHouse Rules brbrReservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No pets unless the $150 non-refundable pet deposit has been paid prior to checkin. Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am

Mins to Downtown in Waterfront community at Pet-friendly Pinecrest Bungalow

Annapolis, Maryland, United States

Bed

Bath

8

Sleeps

$168.31

This listing is for a room within a hotel.brbr✦ Your room is 484 sq. ft, equipped with complimentary toiletries, standard quality 32-inch TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm.brbr✦ Public or shared fitness center open from 6:00AM to 10:00PM, available in the property.brbr✦ Outdoor shared pool available from May 25 to September 5, opened from 9:00AM to 9:00PM.brbr✦ Paid parking lot – 1 space(s), available for $10 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00. 1-4 nights stay, $75 for 5+ nights staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Early & Late Check-outs are subject to availability for a fee.brbr✦ There's a fee for smoking in a non-smoking room. Please ask the Front Desk for locations of designated outdoor smoking areas.

Hotel

Annapolis Adventure: Room w/ Outdoor Pool + Easy Access to Historic Sites

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$172.93

Dive into Annapolis's rich heritage, just minutes from the US Naval Academy and historic downtown. Discover state landmarks and enjoy the ease of exploration from our doorstep!brbrThis listing is for a room within a hotel.brbr✦ Your room is 300 sq. ft, equipped with complimentary toiletries, standard quality 32-inch TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm.brbr✦ Public or shared fitness center open from 6:00AM to 10:00PM, available in the property.brbr✦ Outdoor shared pool available from May 25 to September 5, opened from 9:00AM to 9:00PM.brbr✦ Paid parking lot – 1 space(s), available for $10 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00. 1-4 nights stay, $75 for 5+ nights staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Early & Late Check-outs are subject to availability for a fee.brbr✦ There's a fee for smoking in a non-smoking room. Please ask the Front Desk for locations of designated outdoor smoking areas.

Hotel

Experience Historical Annapolis + Complimentary Breakfast! Outdoor Pool!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$188.65

This listing is for a room within a hotel.brbr✦ Your room is 957 sq. ft, equipped with complimentary toiletries, standard quality 32-inch TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm.brbr✦ Public or shared fitness center open from 6:00AM to 10:00PM, available in the property.brbr✦ Outdoor shared pool available from May 25 to September 5, opened from 9:00AM to 9:00PM.brbr✦ Paid parking lot – 1 space(s), available for $10 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00. 1-4 nights stay, $75 for 5+ nights staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Early & Late Check-outs are subject to availability for a fee.brbr✦ There's a fee for smoking in a non-smoking room. Please ask the Front Desk for locations of designated outdoor smoking areas.

Hotel

Our Welcoming Suite in Annapolis Near Historic Downtown

Annapolis, Maryland, United States

Bed

Bath

5

Sleeps

$349.98

In the heart of Annapolis, where the bay breeze blows, brStands a small cottage, the Captain's Quarters, a peaceful repose.brJust a seven-minute walk to Navy Stadium so grand,brAnd a quick stroll to historic Main Street, hand in hand.brbrNewly renovated, yet with historical charm,brThis snug abode offers a sense of calm.brWith its white picket fence and welcoming air,brYou'll feel right at home in this cozy little lair. brbrInside, the decor reflects nautical themes,brFrom the anchor wall art to the ship in a bottle dreams.brThe cozy kitchen is small but grand,brWith modern amenities at your command.brGleaming gadgets, tools so neat,brReady to make any dish complete. brbrThe bedroom is snug, with a comfortable bed,brWhere dreams of adventure dance in your head. brThe bathroom is cozy, with a cottage feel,brA place to relax and unwind, to heal. brbrSo come stay at the Captain's Quarters, a gem,brA place where memories are made, like a precious emblem. brWith its proximity to all that Annapolis holds dear,brYou'll cherish your time here, year after year. brbrbr

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Annapolis, Maryland, United States

Bed

Bath

5

Sleeps

$457.92

Spacious and charming 5-bedroom Annapolis home just minutes from Downtown Annapolis & the Naval Academy. The main level features 3 bedrooms, including an en-suite, + a fully stocked kitchen, living/dining area, fireplace, & washer/dryer. The lower level includes 2 additional bedrooms, another en-suite, full bath, second kitchen area, fireplace, separate entrance, and its own washer/dryer—perfect for multiple families or groups. Enjoy foosball, a pool/ping-pong table, a fenced backyard, and more!brbrBring the whole family and enjoy this spacious, beautifully designed 5-bedroom Annapolis retreat—perfect for large groups, Navy events, family vacations, business travelers, reunions, and weekend getaways.brbrConveniently located just minutes from Downtown Annapolis, the Naval Academy, shopping, restaurants, and waterfront attractions, this home offers the perfect balance of comfort, entertainment, and relaxation.brbrWhy Guests Love This Homebrbr* 5 spacious bedrooms + 4 full bathroomsbr* 2 private primary suites with en-suite bathroomsbr* Game area with foosball + pool/ping-pong combo tablebr* Large fenced backyard — great for kids & petsbr* Spacious outdoor deck for relaxing or diningbr* 2 kitchens/kitchenette areas — ideal for large groups & extended familiesbr* Smart TVs throughout the homebr* Fast Wi-Fi for work & streamingbr* Quiet, family-friendly neighborhoodbr* Minimal stairs on the main level — convenient for seniorsbrbrAs you enter the home, natural light fills the inviting living area, creating a warm and welcoming atmosphere. Relax by the cozy fireplace, enjoy friendly competition in the game area, or gather together in the open dining and kitchen spaces designed for connection and comfort.brbrThe modern main kitchen features quartz countertops and stainless steel appliances, fully stocked with everything needed for quick meals or large family dinners. A second kitchenette area adds extra convenience for extended families or groups traveling together.brbrStep outside to enjoy the private fenced backyard and spacious deck — perfect for morning coffee, evening conversations, or letting kids and pets play safely.brbrSleeping ArrangementsbrbrBedroom 1 – Primary Suitebr• King-size bedbr• Smart TVbr• Office desk/workspacebr• Private en-suite bathroombrbrBedroom 2 – Primary Suitebr• 2 Queen-size bedsbr• Smart TVbr• Private en-suite bathroombrbrBedroom 3br• Queen-size bedbr• Smart TVbrbrBedroom 4br• 2 Queen-size bunk bedsbr• Smart TVbrbrBedroom 5br• Queen-size bedbr• Smart TVbrbrMain Kitchen & DiningbrFully equipped with:brbr* Quartz countertopsbr* Stove, oven, microwave, refrigerator & dishwasherbr* Coffee maker, toaster, kettle, crock-pot & air fryerbr* Pots, pans, dishes, glassware & utensilsbr* Dining table seating for 6 + additional bar seatingbrbrSecond Kitchenette AreabrIncludes:brbr* Granite countertopsbr* Refrigerator, microwave & stovebr* Coffee maker & essentialsbr* Dining seating areabrbrAdditional Amenitiesbr* Two full-size washers & dryers (one on each level)br* Free high-speed Wi-Fibr* Keyless self-check-inbr* Driveway parking + additional street parkingbr* Pet-friendly (additional fee applies)brbrNearby Attractionsbr* Downtown Annapolisbr* United States Naval Academybr* Quiet Waters Parkbr* Sandy Point State Parkbr* Annapolis Waterfront & City Dockbr* Annapolis Mall & Town Centerbr* Washington, D.C. & National HarborbrbrHouse RulesbrTo maintain a peaceful experience for all guests and neighbors:brbr* No smokingbr* No parties or eventsbr* Quiet hours must be respectedbrbrFor safety and insurance purposes, all guests visiting or staying overnight must be included in the reservation or approved in advance. Additional guest fees may apply above base occupancy.brbrWe look forward to hosting you and helping make your Annapolis stay comfortable, memorable, and relaxing!

Modern Elegance Meets Comfort in Maryland

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$847.68

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to Your Luxury West Annapolis Retreat! brbrNestled in the heart of West Annapolis, this beautifully remodeled craftsman-style home is just one block from popular local restaurants like Evelyn’s, Bean Rush, and the new Agave, and a short 10-minute walk to the Navy Marine-Corps Memorial Stadium. Originally built in 1940 and fully updated in 2016, this home combines the charm of the 1940s with modern luxury and comfort. brbr brbrOutdoor Highlights: brbrThe home sits on a spacious lot featuring: brbrA private fenced backyard with a furnished patio and propane BBQ grill for dining and lounging. brbrA full playset for kids and backyard games like cornhole and croquet. brbrParking for 3-4 cars in the driveway, with additional street parking (no permits needed). brbr brbrIndoor Amenities: brbrThe home offers plenty of room to spread out and relax: brbrMain Floor: A family room, full kitchen with multiple dining areas, and a powder room. The spacious front porch is perfect for morning coffee or evening relaxation. brbrSecond Floor: Four well-appointed bedrooms and two full baths. brbrKing Suite: En-Suite bath, walk-in closet, and TV. brbrTwo Queen Rooms and one Full Room share a stylish full bath in the hall. brbrTop Floor Bunk Room: A fun and cozy kids’ den with twin bunk beds, a desk, sofa, and TV. brbrLower Level: A secondary den with a pool table, a printer/scanner and a full laundry room brbr brbrSleeping Arrangements (Max: 8 adults & 2 kids/teens): brbrKing Suite: 1 King bed, en-suite bath (2nd floor) brbrQueen Rooms (2): 2 Queen beds, shared bath (2nd floor) brbrFull Room: 1 Full bed, shared bath (2nd floor) brbrKids’ Den: Twin bunk beds (2 beds), shared bath (3rd floor) brbr brbrKey Features: brbrFully equipped kitchen with multiple dining areas: brbrDining room table (seats 6-8) brbrBreakfast bar (seats 5), butcher block (seats 2), bar table (seats 4) brbrBackyard dining table (seats 6) brbrBBQ grill on backyard patio (propane included with guest stay) brbrBilliards Table in the lower level Den brbrHigh-speed internet and WiFi brbrFlat-screen TVs throughout brbrLuxury linens, complimentary starter kit with toiletries, and boutique-level service brbrKeyless entry for a seamless check-in experience brbrDog-Friendly Policy: Bring your furry friends for a $150 non-refundable pet fee per pet. brbr brbrPrime Location: brbr1 block to West Annapolis shopping and dining brbr3 blocks to the Stadium brbr1 mile to the U.S. Naval Academy brbr31 miles to Washington, D.C. brbr32 miles to Baltimore brbrHouse Rules: brbr brbrReservations require at least one guest aged 25 or older. brbrNo smoking, parties, or events. brbrRespect the quiet, family-oriented neighborhood and neighbors. brbrCheck-in: 4:00 PM | Check-out: 11:00 AM brbr brbrBook your stay at this charming West Annapolis home, where modern amenities meet timeless elegance, creating the perfect base for your next adventure!

Your Navy Weekend Haven, Family-Friendly Luxury Home w Fenced-in Backyard + Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$246.57

A beautiful basement apartment in the city of Annapolis, in the quiet Eastport neighborhood, a walk to marinas, historic DT Annapolis, and US Naval Academy. Sleeps four, plus two large couches in the living room. A full bath, kitchenette, and a study area. An open living design, great for a short stay. HD TV, Network & Smart TV, and high-speed Internet/WiFi service provided. No pets allowed—free parking- street.

Apartment

Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$426.99

Summary:brYour family will be close to everything when you stay at this charming 2-bedroom cottage nestled in the Eastport area of Annapolis. brbrThe living area boasts ample natural light and the well-appointed kitchen features modern appliances and a breakfast bar, perfect for culinary enthusiasts. brbrThe outdoor space has a patio ideal for outdoor entertaining. Conveniently located near downtown Annapolis, you can enjoy the nearby marinas, waterfront restaurants, and vibrant shopping options.brbrThe Space:brWelcome to our cottage home- the perfect location for your family & friends to enjoy Naval Academy events, boat shows, sailing experiences or just a relaxing getaway.brbrThis cozy home has 2 bedrooms, 2 bathrooms, an outdoor patio and spacious backyard for entertaining.brbrThe well-appointed kitchen is ready and waiting for a family gathering filled with cooking, laughter, and the creation of memories. The kitchen opens into a dining area that can seat 4. With its large bay windows, the living room provides a great space to enjoy natural light and quality time watching your favorite show with friends and family.brbrWhere you will sleep:brbrEach bedroom is designed for comfort, equipped with a TV, ceiling fan and cozy bedding.brbrThe master bedroom has a Queen size bed.brbrThe second bedroom comes with a trundle bed that opens into (2) single beds.brbrThere is dedicated parking for two smaller vehicles in the driveway and street parking is available.brbrCommissioning week rentals are done as a 7-night block from Ring Dance Weekend thru Memorial Day Weekend.brbrOur Eastport home allows for easy access to all that Annapolis has to offer! We are a 15-minute walk to Downtown Annapolis, shops and several restaurants.brbrNOTE: This property follows cleaning and disinfection guidelines provided by the CDC, EPA, and WHO. The home is cleaned thoroughly, and we have disinfected our bathrooms, kitchens, and major touch points like light switches, doorknobs, tabletops, electronics, appliances, and control panels.

Eastport Charmer Summ

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1220.94

Your Fun Filled getaway awaits in Annapolis at this Phenomenal Waterfront House with Hot Tub! With 5 bedrooms including a king sized en suite with additional daybed, 4 queen beds, and a double bunk bed, there's plenty of space for all guests. The 4 bathrooms are equipped with 2 walk in showers, bathtub, hair dryer, and bidet for added convenience. An additional living room with a futon provides even more room to relax. Come experience the park like setting and luxury amenities this property has to offer for your Party, Corporate Retreat, Intimate Wedding, Family Reunion, Graduation Celebration! We hope you enjoy what our place and Annapolis has to offer.

Spacious Waterfront 5-bedroom house in charming Annapolis with Hot Tub

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$435.86

This home is spacious and clean and will make your vacation plans a breeze from this central location. Many families, groups of friends, reunions, wedding parties, boat racing teams and vacationers have enjoyed their stay in our home! brThis charming, immaculate and renovated home on the tip of the Eastport peninsula is directly across from Horn Point Harbor Marina and can be packaged with a slip for up to 110 foot boat. brWalk to downtown Historic District or Naval Academy ~ Plenty of off street parking available, and lots of space for entertaining with a beautiful front porch, a large, fully fenced back yard or enjoy the marina property directly across the street.brWe are certain you will enjoy your stay !brThis home easily sleeps eight people and can accommodate many more for a get-together. Very nicely appointed and comfortable with Annapolis Charm.brbrBack available again is our 13' Boston Whaler ~~ Enjoy a trip up the creek during your stay!brAnd we now have EV charging available as well !brbrKeywords: Home, Family Friendly, Large, Eastport, Parking

Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$416.57

The Chesapeake Bay awaits you at this Annapolis vacation rental! 'Admiral's Post' is situated under 4 miles from the city’s historic downtown. This 4-bedroom, 3.5-bath home is the perfect launch point for your next adventure. Connect with family and friends around the fire pit, fire up the gas grill for a cookout on the deck, and prepare your favorite meals in the kitchen. When you’re not enjoying the comforts of your home away from home, scope out the US Naval Academy, or historic Annapolis!brbr-- THE PROPERTY --brbrAnnapolis STR License STR22-145145 | Indoor Fireplace | Stainless Steel Appliances | WorkspacebrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Twin Sleeper SofabrbrINDOOR LIVING: 2 smart TVs, 2 window A/C units, 6-person dining table, walk-in closetbrKITCHEN: Stove/oven, microwave, refrigerator, blender, coffee grinder, coffee maker, toaster, cooking basics, dishware/flatware, dishwasher, garbage disposal, ice maker, water filter, spicesbrGENERAL: Free WiFi, central air conditioning, washer/dryer, linens/towels, complimentary toiletries, hair dryer, iron/board, trash bags/paper towelsbrACCESSIBILITY: 3-story home, stairs required to access, 2 bedrooms on basement levelbrFAQ: 2 exterior security cameras (facing out)brPARKING: Garage (1 vehicle), driveway (1 vehicle), free street parking (first-come, first-served)brbr-- THE LOCATION --brbrNEARBY ( 1.0 miles): Starbucks, Dunkin', CVS, 7-Eleven, Giant Food, PNC Bank, Rocco's Pizza, Jack's Fortune Chinese RestaurantbrUS NAVAL ACADEMY: US Naval Academy Museum (3.8 miles), Alumni Hall (4.0 miles), Navy-Marine Corps Memorial Stadium (4.1 miles), Memorial Hall (4.5 miles) brHISTORIC DOWNTOWN: Annapolis Maritime Museum & Park (3.1 miles), Annapolis City Dock (3.4 miles), Maryland State House (3.6 miles), William Paca House & Garden (3.7 miles) brOPT OUTSIDE: Quiet Waters Park (2.1 miles), Annapolis City Marina (2.8 miles), Sandy Point State Park (12.6 miles), Herrington Harbour South (26.8 miles)brSHOPPING: Annapolis Town Center (4.9 miles), Westfield Annapolis Mall (5.7 miles), Arundel Mills (23.4 miles)brAIRPORT: Baltimore/Washington International Thurgood Marshall Airport (25.6 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Three steps are required to access the front door, and eight steps are required to access the backyard from the back deck. There are two bedrooms on the top floor and two bedrooms on the basement level. All bedrooms require stairs to accessbr- NOTE: Street parking is available across the street from the property. Cars cannot be parked in front of the home due to the community mailboxbr- NOTE: Your safety matters. This property features 2 exterior security cameras: 1 camera is located on the front entrance facing the driveway, and 1 camera is on the back of the house facing the garden. They are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$547.91

Looking to explore Annapolis and live comfortably on a budget This cozy square house will be just right for you! The single family house is situated in a very convenient location! Bus stop right across the street, close to the west street, lots of restaurants and fun places, only 5 minutes drive to downtown Annapolis and Naval Academy. Relax with the whole family at this peaceful place to stay.

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$733.07

brExperience coastal charm and modern comfort at Voyagers’ Nest, a spacious 5-bedroom retreat near downtown Annapolis and the U.S. Naval Academy. Enjoy two living rooms, a fully equipped kitchen, and a private fenced backyard—perfect for families and groups. Your stylish home base for exploring Maryland’s historic waterfront city.brbrThis wonderful 5-bedroom gem in Annapolis features 3 king beds, 2 queen beds, 1 twin bed, 1 trundle bed. With amenities like AC, heating, and an iron, guests will have an enjoyable stay. The 2 bathrooms come equipped with a hair dryer, shower, and bathtub. Your phenomenal vacation awaits at this lovely property. We'll be available to answer any questions while you stay at our place.

5 bedroom house with EV charger Near Downtown Annapolis

Annapolis, Maryland, United States

5

Bed