Vacation Home Rentals By Owner In Annapolis, MD

Welcome to your 5 ⭐️ Annapolis home base for families, sailing crews, and group getaways. This spacious 4-bedroom home comfortably sleeps up to 12 guests and is located less than 5 minutes from the water and just 10 minutes from historic downtown Annapolis, the Naval Academy, waterfront dining, and local events. brbrCape St. Claire hosts its own July 4th parade and beach celebration — enjoy the morning festivities on foot, then head 10 minutes to downtown Annapolis for the harbor fireworks at 9:15pm before returning to the spacious firepit and basement bar to close out the night.brbrDesigned with groups in mind, the home offers plenty of space to gather, relax, and unwind. Enjoy a huge private backyard featuring a fire pit, cornhole, and a putting green—perfect for afternoons outside or evenings around the fire. Inside, the basement bar and entertainment area create an ideal space for nights in after a day on the water or downtown.brbrThe fully stocked kitchen makes hosting easy, with multiple appliances, all cookware and utensils, complete dishware, and a dedicated coffee bar with complimentary coffee and tea. A large dining area allows everyone to sit together comfortably for meals, games, or planning the next day’s adventures.brbrFor guests working remotely, the home includes a dedicated desk and fast Wi-Fi throughout. Free on-site parking and easy self check-in make arrival and departure simple. Pets are welcome with approval, making this a great option for families traveling with furry companions.brbrWhether you’re visiting for spring sailing events, graduations, weddings, or a weekend escape with friends, this home offers the space, comfort, and location to make your stay easy and memorable. Prime dates book quickly—early reservations are strongly recommended.brbr✦ What our guests love about our listing: ✦brbr-Check-in process: Keyless entry with codebr-Parking: Multiple-Car Driveway.br-OFFICE SPACE: Quiet area with spacious desk and comfy, supportive chair for remote work and extended staysbr-Coffee: Free K cups and Ground Coffee providedbr-Laundry: In unit washer and dryerbr-Queen-Sized Air Mattress for extra accommodationbr-Activities: Outdoor Firepit with Hammock, Regulation Size Cornhole Boards, and Indoor/Outdoor Putting Greenbr-Lightening fast WiFi on our two large 75 and four 55 SMART TV's.br-Four HUGE Queen Bed's with luxurious sheetsbr-Professionally cleaned and sanitized between each and every guest.brbrApproximate Travel times:br➤ Broadneck Park - 2 Minutesbr➤ Sandy Point State Park - 7 Minutesbr➤ Bay Hills Golf Club - 7 Minutesbr➤ Navy-Marine Corps Memorial Stadium - 10 Minutes ➤ Historic Downtown Annapolis - 11 Minutesbr➤ Annapolis Mall - 12 Minutesbr➤ US Naval Academy - 12 Minutesbr➤ Annapolis Landing Marina - 19 Minutes Landscaping occurs bi-weekly. Please understand they may perform service during your stay.brbrIf you want to be notified in advance, please inform us upon check-in.

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$357.9

Immerse yourself in the rich history of Annapolis at our century-old home in Presidents Hill. With 3 bedrooms, 2 baths, and classic features, it's a cozy retreat and perfect home base for all there is to do in Annapolis.brbrWhether you're exploring historic streets, dining al fresco downtown, enjoying the waterfront activities, or here to cheer “Go Navy”, our home is the perfect base for your Annapolis adventure. brbrThis home is a 5 minute walk to everything in downtown Annapolis - USNA stadium, shopping, Main Street, museums, water taxis, waterfront dining, restaurants and more.brbrReturn home and relax in the charming backyard or curl up with a good book. Book today.br

Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$391.45

Built in August 2025 | Group-Friendly Layout w/ 4 En-Suite Bedrooms | 1 Mi to Shopping, Dining & HospitalsbrbrSpacious and stylish, this 4-bed, 4.5-bath home makes your Annapolis adventure feel effortless! Each en-suite bedroom offers a private place to recharge, while the open living room and patio offer space to gather. Shop at Annapolis Mall, tour the Naval Academy, or wander cobblestone streets of Historic Downtown, then return to a vacation rental designed with modern comfort in mind.brbr-- THE PROPERTY --brbrSTR-01110brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 queen bedbr- Bedroom 4: 1 king bedbrbrTOWNHOME HIGHLIGHTSbr- Smart TVbr- Large dining tablebr- Private ensuite bathroomsbr- 2,600-square-foot interiorbr- Furnished balconybr- 2 floor-length mirrorsbrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Keurig, coffee & tea providedbr- Toaster, microwavebr- KitchenAid mixerbr- Cooking & baking basics, dishware & flatwarebrbrGENERALbr- Free WiFibr- Central A/C & heatingbr- Washer, dryer, laundry detergent/fabric softenerbr- Iron & board, drying rack, cordless vacuum cleanerbr- Linens & towels, shampoo & conditioner, body washbrbrACCESSIBILITYbr- Multi-level townhome, 2 steps to enterbr- Interior stairs required to access kitchen & living areasbr- Bedroom & bathroom on level 1brbrPARKINGbr- Driveway (2 vehicles)br- Free street parking (first-come, first-served) br- EV outlet available (bring your own charger)brbr-- THE LOCATION --brbr- 1 mile to Luminis Health Anne Arundel Medical Center & Children's National Hospitalbr- 2 miles to Navy-Marine Corps Memorial Stadium & Annapolis Mallbr- 3 miles to Annapolis City Dock & Historic District: dining, shops, museumsbr- 3 miles to United States Naval Academy & St. John's Collegebr- 9 miles to Sandy Point State Parkbr- 25 miles to Washington, D.C.br- 22 miles to Baltimore/Washington Int'l Airportbrbr-- 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-inbrbrADDITIONAL INFORMATIONbr- This multi-level townhome requires 2 steps to enter. There is a bedroom and a full bathroom on the 1st floor. Interior stairs are required to access the kitchen and living areas

Modern Gem Near Historic Annapolis & Naval Academy

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$450.24

Enjoy your stay in our charming home centrally located directly across from Navy-Marine Corps Memorial Stadium on Taylor and in walking distance to downtown. For navy tailgating, you just can't get any closer! Upon your arrival, hang up your car keys and enjoy strolling through our quaint town or use one of the multiple transportation options. You're in the midst of it all!! We look forward to welcoming you to our home!brbrEnjoy our historic, cozy bungalow, built with love from our own grandfather's hands. A unique sandstone home built in 1920 with updates and comfort of 2020. A true gem nestled in the heart of Annapolis! Read a book in the rockers on the screened in porch or light a fire and relax by the Solo Stove firepit on the patio. Whether you prepare your dinner on the grill outside or in the spacious, well lit and well appointed kitchen, you'll enjoy every aspect of this house and will feel right at home during your visit!brbrA terrific place to walk or run! A wonderful, paved, mile long trail awaits you directly across the street at the stadium. Or you may walk 1/2 mile to the Arts District on West St. or 1/4 mile to West Annapolis- both locations offering restaurants and some boutique shopping. Historic Annapolis and the top of Main St is only a mile away offering more shops and eateries! We have left recommendations of some of our favorite places in the guidebook at The Bungalow.brbrWe live adjacent to the property and can be as available as needed during your stay. Outdoor maintenance and yard work is ongoing and may take place during your stay. However, it will not take place without first discussing with you, our guest, as we do not want to impose upon your stay or interrupt any activities you may have planned.brbrGuests have access to the upper level of the home as well as the laundry. The laundry is in the lower level along side of the garage. The owner has tools in the garage that are not to be used by the tenant. The owner may access these tools through the garage door which is a separate entrance than that which the tenants use for accessing the home.

Dog friendly! Next to Navy Stadium and DTA Shuttle!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$952.41

This is the perfect house for your family friendly visit to Annapolis, MDbrbr*Please no bachelor/bachelorette partiesbrbrEnjoy everything the sought after Eastport neighborhood has to offer. Very short walk to bars, restaurants, shops and even a brewery!brbrCity Dock/Ego Alley is less than one mile away & the Navy Yard is 1.1 miles away. brbrComing in for a Navy game The Stadium is 2.3 miles (9 min drive)brbrOur house has a fenced in yard, with two patio areas and two fire pits. brbrEnjoy playing pool, shuffleboard and darts in our game room!

Annapolis/Eastport 4 BR w/ Game room - Walk everywhere!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$299.82

Enjoy the close proximity to all Annapolis has to offer at this row house located next to college creek. Nicely decorated and cozy! There is a queen bed in each room as well as a sofa which folds into an additional queen bed. The yard offers seating and a charcoal grill and there's a balcony off the bedroom for private outdoor enjoyment. Home is equipped for cooking and hanging out if you prefer to stay home. But if you are out on the town enjoy the ease of only a 10 minute walk to West Street where you will find great restaurants and church circle. Only 20 minute walk to the naval academy and downtown so we park the car in the house's own parking in the rear off the street. No need to fuss with parking downtown! If in town for a Navy game, the Stadium is only a 10 minute walk.

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$622.44

Welcome to your dream stay nestled in the heart of Historic Downtown Annapolis! Located just 45 feet from downtown Annapolis's City Dock and 150 feet from the main entrance of the U.S. Naval Academy!brThis stunning 4-bedroom (5 bed), 3-bath home offers the perfect blend of southern charm, luxury, and an unbeatable location for walking to everything! Whether you're visiting for a Naval Academy event, a weekend getaway, nautical event, or a family gathering, this property is your can't-pass-up home base!brInside, enjoy a spacious layout designed for comfort and togetherness. Each of the three full bathrooms features a custom walk-in shower, and each of the four bedrooms is uniquely styled for relaxation after a day of exploring this beautiful town.brbrWhen you're not enjoying the walkable beauty of Annapolis, retreat to the private back patio, where string lights twinkle above cozy seating under the pergola and a propane grill invites you to fire up a home cooked meal under the stars!brbr Sleeps 8 | 3 Full Baths | Historic DistrictbrbrKey Amenities:brbr- Prime location: 45 feet from downtown, 150 feet from USNA Gatebrbr- 4 private bedrooms (5 beds) with comfortable bedding and foam mattressesbrbr- 3 full bathrooms with custom walk-in showersbrbr- Fully equipped kitchen with modern appliancesbrbr- High-speed Wi-Fi & smart TVsbrbr- Charming back patio with string lights, outdoor seating, and propane grillbrbr- Central air conditioning & heatingbrbr- Washer/dryer in-unitbrbr- Coffee station (fully stocked) to jumpstart your morningsbrbr- Multiple parking garages under 1 mile from the property (pay to park street parking also available with a 2-hour maximum time limit)brbrWhether you're here for history, celebration, or relaxation, this property offers a five-star experience with an authentic Annapolis backdrop creating the perfect getaway you've been looking for!

Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!

Annapolis, Maryland, United States

Bed

3

Bath

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

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

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

1

Bed

1

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

$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

3

Bath