Vacation Rentals By Owner In Annapolis, MD

$255.36

Governor Calvert King Balcony at Historic Inns of Annapolis | Pets Allowed

Annapolis, Maryland, United States

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 280 sq. ft, equipped with complimentary toiletries, high definition 42-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 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

1

Bed

1

Bath

2

Sleeps

$385.27

/ Nightly

Hotel

Governor Calvert Suite at Historic Inns | Steps to Maryland State House

Annapolis, Maryland, United States

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 200 sq. ft, equipped with complimentary toiletries, high definition 42-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 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

Bed

Bath

Sleeps

$2257.2

/ Nightly

Private Vacation Home

Cool 1870's home anchored in the Historic District with modern amenities.

Annapolis, Maryland, United States

Our century-and-a-half-old, five bedroom and three bath home with 3,000 square feet centrally situated in the heart of the Annapolis Historic District downtown. brbrYou'll be 3-4 blocks from the Naval Academy, Main Street shops, food and the historic State Capital. brbrOurs is a Federal style, circa 1870's, three story brick row home which was partially upgraded in 2017. Renovation included gutting both the kitchen and the English basement bedroom. brbrEnjoy a screened porch overlooking a private garden surrounded by an eight foot tall brick wall. There is plenty of space throughout the home with hideaways where you can relax and get away from it all.brbrThere are three full baths - the second floor has a walk in shower. The master bathroom has a claw foot tub combination shower. The renovated English Basement, which is the fifth bedroom, has the third full bath with a walk in shower. Although we permit up to ten guests, there are five beds: a California King, a queen, a sleeper sofa queen in the English basement and two double beds on the second floor. There are two queen inflatable’s stored in the English basement.brbrThe rear bricked patio has a Weber gas grill and a Solo fire pit and it is surrounded by an 7-8 foot high brick wall. The rear screened porch behind the kitchen is our favorite go to space for sharing pleasant weather or streaming to the the overhead TV screen.brbrWith its walk-to-everything coordinates, creaky heart pine floors, tall ceilings and upgraded amenities, you'll feel a warm coziness throughout our old brick home. brbrThe English Basement bedroom has three entrances including a rear door to the brick walled patio.brbrYou can come and go from the English basement bedroom through the interior stairs or through the lower level front door which takes you up the brick steps directly to Prince George Street. brbrThere is a small laundry on the second floor and two large capacity LG laundry machines in the English Basement.brbrNon-smokers only. This is our 'real' home, we live here when not renting. Our home is for mellow family events. brbrNo on site parking - Calvert Street Garage at 19 St. Johns St. is free on weekends and after 6pm daily. Hillman Garage at 150 Gorman St. has 24 hr parking @ ~$30 daily. br(rev July 27, 2025)

Bed

Bath

Sleeps

$396.41

/ Nightly

Private Vacation Home

Charming Charles -Walkable Downtown Annapolis Home

Annapolis, Maryland, United States

Summary:brbrEscape to your private oasis in this stylish 2-bed, 2.5-bath townhome in the heart of Downtown Annapolis. This historic yet modern retreat features a fully equipped kitchen and a charming private patio. Perfectly located, you're just a short walk from the historic district, waterfront, and renowned restaurants. Ideal for a weekend getaway or Naval Academy event, experience the best of Annapolis from this perfect home base.brbrbrbrThe Space:brbrWelcome to our inviting 2-bedroom, 2-bathroom townhome in the picturesque city of Annapolis. Step inside and discover a cozy yet spacious retreat, thoughtfully designed to provide comfort and convenience. The open concept living area invites relaxation with its stylish furnishings and ample natural light. The fully equipped kitchen offers modern appliances and a dining area for enjoying home-cooked meals. brbrbrbrRetreat to the tranquil bedrooms, each boasting plush beds and tasteful decor, ensuring a restful night's sleep. The townhome features 1 half bathroom on the main level and two full size bathrooms, each featuring contemporary fixtures and complimentary toiletries. brbrbrbrOutside, a charming patio awaits, perfect for sipping your morning coffee or unwinding in the evening breeze. Situated in a desirable neighborhood, you'll find yourself in close proximity to Annapolis' renowned attractions, including the historic district, waterfront, and shopping destinations. Whether you're here for a weekend getaway, Naval Academy event or an extended stay, our 2-bedroom townhome provides a comfortable haven for exploring all that Annapolis has to offer.brbrbrbrKey Features:brbr* **Living Area:** Open-concept with stylish furnishings and historic exposed brick.brbr* **Kitchen:** Fully equipped with modern appliances and an adjacent dining area, perfect for home-cooked meals.brbr* **Bedrooms:** Two tranquil bedrooms, each boasting plush beds and tasteful, coastal-inspired decor.brbr* **Bathrooms:** Two full en-suite bathrooms with contemporary fixtures and complimentary toiletries, plus a convenient half-bathroom on the main level.brbr* **Outdoor Space:** A charming, private brick-paved patio, an ideal spot for sipping your morning coffee or unwinding in the evening breeze.brbrbrbrRENT-000713-2025brbrbrbrGuest Access:brbrGuests will have private and exclusive access to the entire townhome throughout their stay, including the private patio. Enjoy the comfort and privacy of having the whole space to yourselves.brbrbrbrThe Neighborhood:brbrDowntown Annapolis is a historic and charming neighborhood. It is nestled along the shores of the Chesapeake Bay and is known for its picturesque streets lined with beautifully preserved colonial buildings. The area offers a blend of maritime heritage, boutique shops, restaurants, and lively waterfront activities. With its cobblestone streets and iconic landmarks like the Maryland State House and the United States Naval Academy, downtown Annapolis is a popular destination for both tourists and locals alike. The vibrant atmosphere, rich history, and scenic waterfront make it a delightful place to explore and immerse yourself in the city's maritime culturebrbrbrbrGetting Around:brbrOnce you get settled in the home, there are several places to explore and visit within walking distance. There are also several ride share options available.brbrbrbrOther Things to Note:brbrDue 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 detailsbrbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a self-check-in process for your convenience. While we will not be present during your stay, we are always available via the messaging app or phone if you have any questions or need assistance.

Bed

Bath

Sleeps

$421.8

/ Nightly

Private Vacation Home

Charming 3-bedroom house in Annapolis Eastport! Beautifully furnished home

Annapolis, Maryland, United States

Beautifully furnished 3 bedroom, 2 bath home, available for short or long term rental in Eastport Annapolis! 4 minutes uber to ego alley, 15/20 minutes walk to all Eastport restaurants and shops. Naval Accademy less than 2 miles away. Perfect for families heading out to Naval Accademy functions, graduation, or the Annapolis boat shows! Also perfect for graduate student waiting for move, or for a vacation spot in the heart of Eastport Annapolis. Please contact home owner for all inquiries. Kane 513-748-6823. Stay comfortably in Annapolis at this 3-bedroom house. Marvelous bedroom setup includes 2 full beds and 1 bunk bed. Enjoy the convenience of WiFi, heating, and AC. With 2 bathrooms equipped with a hair dryer, guests will feel right at home. We hope you enjoy what our place and Annapolis has to offer.

Bed

Bath

Sleeps

$733.0

/ Nightly

Private Vacation Home

DISCOUNTED FOR USNA COMMISSIONING WEEK 2024 and 2025! Short term and weekends.

Annapolis, Maryland, United States

Beautiful, remodeled 3 BR home with stunning great room addition, 20' x 20' screened, covered porch with newly added outdoor deck allows you to BBQ on a propane weber grill while you socialize. A marbled wall entrance with compass rose floor inlay greets your arrival. Six ceiling fans grace cathedral and standard ceilings, providing an airy retreat. Screened in porch with couch, glass top dining table and eight cushioned chairs provides relaxation. Three full baths are remodeled with marble walls and floors. Three bedrooms with two King beds and one double. Trundle bed in separate, semi-private area opens to two twin beds. Sleeps 8 with current beds and up to 10 with the Queen air mattress provided by homeowner. Linens (sheets, towels), fresh bars of soap, paper towels, TP, dish soap, etc are provided to ensure you enjoy your time in Annapolis and you don't need to run to the store for staples.brbrThree HDTVs, DVD player, surround sound and wifi are some of the amenities. Two HVAC units allow you to adjust temperature to your comfort.brbrWell behaved, house broken, adult dogs are considered for a $180 non refundable pet / cleaning fee. Certain breeds or chewers may not be approved. Please contact homeowner to discuss pets. No cats, please! :) Anchorage Community about 2 miles from USNA Stadium and walking distance to Bay Ridge views.brbrKeywords: Gorgeous, remodeled Annapolis home. 2-3 mi from downtown Annapolis. Ideal for Boat Shows, Naval Academy Graduation and events, Sailing, sightseeing, water sports, antiquing, and more. brbrBeautifully landscaped yard and relaxing 20 x 20+ screened in porch with glass deck table, chairs, and hammock. Screened in porch has door to outside deck with gas grill. Established community with pool/water privileges/Lake Ogleton, Visitors are encouraged to enjoy scenic 5 miles walk/bike ride round trip around Bay Ridge with stunning views of the Chesapeake and Severn River.brbr3 night minimum

3

Bed

3

Bath

10

Sleeps

$204.06

/ Nightly

Hotel

Boutique Historic Stay Near USNA & Annapolis City Dock | 1 King Bed

Annapolis, Maryland, United States

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 280 sq. ft, equipped with complimentary toiletries, high definition 42-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 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

1

Bed

1

Bath

2

Sleeps

$204.06

/ Nightly

Hotel

Robert Johnson 1 King Bed Pure Wellness Room at Historic Inns of Annapolis

Annapolis, Maryland, United States

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 280 sq. ft, equipped with complimentary toiletries, high definition 42-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 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

1

Bed

1

Bath

2

Sleeps

$210.9

/ Nightly

Hotel

Maryland Inn | Victorian Charm | Queen Room | 0.1mi State House

Annapolis, Maryland, United States

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 247 sq. ft, equipped with complimentary toiletries, high definition 42-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 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

1

Bed

1

Bath

2

Sleeps

$210.9

/ Nightly

Hotel

Robert Johnson 1 Queen Bed Pure Wellness Room at Historic Inns of Annapolis

Annapolis, Maryland, United States

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 247 sq. ft, equipped with complimentary toiletries, high definition 42-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 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

Bed

Bath

Sleeps

$436.55

/ Nightly

Apartment

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Annapolis, Maryland, United States

Charming private space in a quiet neighborhood. Live like locals and enjoy walking or biking around town. Free street parking, one block to Navy Stadium, 1 mile walk to downtown Annapolis and Naval Academy, 30 min drive to Baltimore or BWI and 45 min to Washington DC. brBeautiful, immaculate private space. brSafely tucked away a charming carriage house apartment in private backyard - 2 bedrooms, family room, well equipped kitchen and sparkling clean shower and bath. brPets welcomed but must be approved in advance +$50 pet fee per pet, per stay.brNote - 7 night min. during USNA Commissioning Week. br2 night minimum preferred, but will accept one night bookings. brPlenty of toys for toddlers and babies, games for older kids. Highchair and pack & play. brWe have several bicycles available to use, different sizes for different ages, please ask. brOutdoor space in the yard for toddlers to play. Also ask for corn hole and other yard games to use. brCozy fire pit area to enjoy, please ask for wood or bring your own. brSchool fields near by and beautiful nature walking path right in front of the house. Please use the path for all pet bathroom needs not the backyard space. brHope you enjoy and relax in Annapolis!

Bed

Bath

Sleeps

$640.59

/ Nightly

Private Vacation Home

Beautiful Annapolis Home Near the Beach with a fitness room

Annapolis, Maryland, United States

Enjoy luxury coastal living perfect for families and friend groups in this newly remodeled Annapolis retreat. Located in peaceful, walkable Cape St. Clair with access to the private beach. Relax by the outdoor fireplace, host movie nights in the home theater, or grill outdoors. With a gym, office, and short drive to the Naval Academy and downtown, comfort and convenience meet by the bay.brbrThe home features 4 bedrooms (2 queen beds, 1 full bed, 2 bunk beds) with smart TVs in the two queen bedrooms and full bedroom. Enjoy 3 full bathrooms stocked with hand soap, body wash, shampoo, and conditioner.brbrEntertainment is easy with a home theater (4K projector, surround sound, wireless streaming), a pool table, board games, and a home gym with a stationary bike and multi-function utility machine offering 40+ workouts. A selection of books, complimentary coffee and tea, and smart check-in/check-out make your stay effortless.brbrOutdoors, relax under the pergola by the fireplace, dine at the outdoor table, or enjoy the balcony with a coal grill and cozy seating. Guests also have access to the private Cape St. Clair community beach, just a short walk away.brbrIdeal for family vacations, friend getaways, or peaceful escapes by the water, this home blends comfort, style, and entertainment for an unforgettable Annapolis stay.

4

Bed

3

Bath

11

Sleeps

$273.98

/ Nightly

Cottage

Idyllic Cottage Near Annapolis with Treehouse Vibes & Outdoor Charm

Annapolis, Maryland, United States

Conveniently located just minutes from historic downtown Annapolis. Whether you're planning a romantic retreat, a family vacation, or a weekend with friends, this idyllic cottage is the perfect place to make lasting memories. The highlight of this property is the stunning outdoor space that makes you feel like you're staying in a treehouse. Step out onto the deck to enjoy your morning coffee or take a short walk to the neighborhood park.

1

Bed

1

Bath

4

Sleeps

$626.48

/ Nightly

Private Vacation Home

Quiet Woodland Lodge w Community Beach Access & Large Private Deck

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to The Woodland Lodge brbrTucked at the end of a quiet cul-de-sac in the water-privileged community of Annapolis Roads, this 4-bedroom, 3-bath home offers privacy, comfort, and coastal charm. Surrounded by a beautifully landscaped yard, enjoy a spacious furnished deck perfect for relaxing or dining outdoors. Inside, the bright, open layout flows into a stunning two-story family room with soaring ceilings, natural light, and a cozy pellet stove fireplace. brbr brbrLocated just 10 minutes from downtown Annapolis, with access to a community beach and playground, this home is the perfect Chesapeake Bay retreat. brbr brbrSleeping Arrangements - 4 Bedrooms, 3 Baths, Sleeps 8 brbrThird-Floor Suite brbrCalifornia King bed brbrEn suite luxury bath with double vanities, Jacuzzi tub, and stand-up shower brbrPrivate Loft overlooking family room brbrFlat-screen TV brbr brbrFront Queen Bedroom (Main Floor) brbrQueen bed brbrShared full bath with combo bathtub/shower brbr brbrBackyard-Facing Queen Bedroom (Main Floor) brbrQueen bed brbrShared full bath with combo bathtub/shower brbr brbrLower Level Bedroom brbrQueen Bed brbrFull bath with shower in the hall brbrAccess to back patio and yard brbr brbrHighlights brbrLarge Private furnished deck with table with seating for 4 brbrSmoker grill and wood-burning Solo Stovefire pit brbrDining room table for 6 plus seating for 2 at the breakfast bar brbrLofted office on the second floor brbrCommunity amenities include: beach, playground, fire pit and launching pier brbrHigh-speed internet and WiFi brbrFull house back-up power generator brbrFlat-screen TVs in every bedroom and all of the living spaces brbrLuxury linens, starter toiletries, and boutique-level service brbrDriveway and cul-de-sac parking for 4-5 cars brbrFull laundry room with washer and dryer brbrDogs allowed with $150 non-refundable fee due prior to checkin. brbrKeyless entry for a seamless check-in experience brbr brbrDistances brbrDowntown Annapolis: 3 miles brbrU.S. Naval Academy: 3 miles brbrWashington, DC: 33 miles brbrBaltimore: 32 miles brbr brbrIncluded Amenities brbrStarter pack with coffee, sweeteners, soap, shampoo, conditioner, lotion, hand sanitizer, paper towels, toilet paper, dish soap, and dishwasher detergent brbrFreshly laundered, ready-made beds with clean towels brbr brbrHouse Rules brbrThe primary guest must be at least 25 years old. brbrQuiet hours must be respected in this family-friendly neighborhood. brbrNo parties, events, or smoking of any kind. brbrCheck-in: 4:00 PM | Check-out: 11:00 AM brbr brbrWhether you're visiting for a relaxing getaway or a special gathering, this Annapolis Roads retreat offers everything you need for a memorable stay.

4

Bed

3

Bath

8

Sleeps

$371.61

/ Nightly

Hotel

Maryland Inn Suite at Historic Inns of Annapolis | Pets Are Allowed

Annapolis, Maryland, United States

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 200 sq. ft, equipped with complimentary toiletries, high definition 42-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 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $150.00 (per pet). for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

1

Bed

1

Bath

4

Sleeps

$182.4

/ Nightly

Hotel

Elegant Historic Flat: Near State House & Naval Academy | Pets Are Allowed

Annapolis, Maryland, United States

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 250 sq. ft, equipped with complimentary toiletries, high definition 42-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 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $150.00 (per pet). for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

1

Bed

1

Bath

2

Sleeps

$182.4

/ Nightly

Hotel

Maryland Inn Queen at Historic Inns of Annapolis | Pets are Allowed

Annapolis, Maryland, United States

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 250 sq. ft, equipped with complimentary toiletries, high definition 42-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 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $150.00 (per pet). for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

1

Bed

1

Bath

2

Sleeps

$371.61

/ Nightly

Hotel

Pet-friendly Accommodation at Historic Inns of Annapolis | 0.3 mi to State House

Annapolis, Maryland, United States

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 200 sq. ft, equipped with complimentary toiletries, high definition 42-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 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $150.00 (per pet). for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

Bed

Bath

Sleeps

$663.64

/ Nightly

Private Vacation Home

Adorable cottage! Walking distance to USNA & downtown! (VRBO only)

Annapolis, Maryland, United States

Listing will never be posted on Craig's list - VRBO only **Adorable 1930's cape cod, located in the historic Murray Hill neighborhood. Off street parking and walking distance to great restaurants, bars, shows and US Naval Academy and stadium. Cute, cozy and fun, decorated in vintage mid century style to match when the home was built. Super cute backyard and patio - a romantic oasis covered with twinkling lights, an amazing venue for a small family gathering, wedding, or party (additional fee would apply, contact owner). (VRBO ONLY* THIS LISTING WILL NEVER BE ON CRAIGS LIST*)

Bed

Bath

Sleeps

$849.3

/ Nightly

Private Vacation Home

Annapolis -Eastport - -3 Bedroom- 3 bath with parking

Annapolis, Maryland, United States

Delightful Arts and Crafts/ Coastal style home. Main Level is open space concept with 9 ft ceilings and plenty of natural light, walk out to large yard and patio for grilling entertaining. brSecond floor Master Suite and two Guest bedrooms each with walk in closet and full bath. 1/2 mile walk to Naval Academy Gate 1 and Downtown brAnnapolis HarborbrOpen concept is great for relaxing and entertaining..

3

Bed

3

Bath

8

Sleeps

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