House holiday rentals in Annapolis

The exterior of a charming historic building features a welcoming front porch adorned with seating. Lush green trees and blooming flowers enhance the inviting atmosphere. American flags are displayed, highlighting the traditional character of the neighborhood.

4.99 out of 5 average rating, 153 reviews

Elegant & Authentic Annapolis

Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.

FamilyValueComfort

The layout of the home is depicted in an illustrated floor plan, showcasing three distinct areas. Each level features various rooms, including bedrooms, a living space, and a kitchen area, with labels indicating the functions of different spaces.

4.97 out of 5 average rating, 152 reviews

Villa Annapolitana • Parking 1 min • USNA 4 min

Our 1700s home offers a perfect blend of luxury and comfort. With three beautiful bedrooms, three bathrooms, and a sleek lounge area, it’s a perfect place to relax and unwind. The fully stacked kitchen is ready and waiting for you to cook a perfect meal and enjoy a glass of wine. The location is ideal, with the US Naval Academy just a 5-minute walk away. If you are looking for a peaceful escape or a fun vacation, our property has something for everyone. ✔ King Beds ✔ Smart TVs ✔ Sport Equipment

LocationFamilyGetting around

4.95 out of 5 average rating, 256 reviews

Sailboats are moored in a serene marina, with soft waves reflecting the sunlight. The docks are lined with wooden posts, guiding the view to a lush green shoreline in the background. A peaceful atmosphere is created by the gentle ripples and warm evening light.

Home in Edgewater

Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

FamilyValueAir conditioning

5.0 out of 5 average rating, 117 reviews

Modern Annapolis Getaway - 2 Free Parking Spaces

Modern 2 bedroom, 1 bath home located in the heart of historic Annapolis. Completely remodeled with free off-street parking. Located towards the end of a safe, quiet, dead end road, less than 3 miles from downtown Annapolis, the Naval Academy, the Annapolis Mall, St. John’s College, and the Navy-Marine Corps Memorial Stadium. Walk downtown or to the Annapolis Town Center, restaurants, shops, and so much more! -Wi-Fi -2 free parking spaces -Keurig Coffee -TV -Toothbrushes/Paste -Shampoo/Soaps

ValueFamilyLaundry

4.99 out of 5 average rating, 145 reviews

A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.

Home in Stevensville

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

FamilyValueOutdoor spaces

4.9 out of 5 average rating, 226 reviews

A tranquil view of the Chesapeake Bay is captured, showcasing a grassy expanse leading to the water. Two stone boundary walls are visible, framing the lush landscape. A solitary beach umbrella and chair rest on the shore, inviting relaxation by the calm water.

Home in Cape St. Claire

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

FamilyValueParking

A spacious living area showcases a comfortable sectional sofa and a leather armchair beside a decorative rug. A modern fireplace is framed by a white mantel, while a large television is mounted on the wall. A view of the stylish kitchen is visible in the background.

4.98 out of 5 average rating, 99 reviews

Downtown Annapolis Luxury House

Our downtown luxury Annapolis getaway is located 1.4 miles from Church Circle, which is the heart of downtown Annapolis. We are walking distance to all the amazing attractions in Annapolis. Our house is a lovely blend of comfort and style, making it an ideal retreat for families, friends, or colleagues traveling together! We are happy to offer early check-in and late checkouts if our bookings allow. Please contact us today and reserve our house for your next Annapolis getaway!

ValueLocationBackyard

4.97 out of 5 average rating, 100 reviews

Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit

Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier/dock! Gorgeous sunrises! Experience fresh Maryland Crabs & fish caught from your private pier & enjoy the peace, serenity, bay breezes & waterfront green space! Connect to nature and explore Meredith Creek on the Chesapeake Bay by kayak or boat! Super CLEAN & new with water views from dining, living room, kitchen and bedroom! 1.5 miles to the Beach!

ValueFamilyQuiet

A modern kitchen features a large island with seating for four. Sleek cabinets and stainless steel appliances create a functional cooking space. Unique pendant lights hang above the island, complementing the stylish countertop. The open layout allows visibility to the living area beyond.

4.91 out of 5 average rating, 122 reviews

Fleet St Retreat in Downtown - Great Location!

We welcome you to our renovation on historic Fleet Street. Purchased in 2016 this house was taken down to the studs so everything is brand new and waiting to host you on your next trip to Annapolis. Literally a stones throw from everything downtown has to offer you can’t get closer to the action. USNA, Maryland State House, City Dock, McGarveys and Iron Rooster are just around the corner. Perfect place for two couples and a extra single. Small city patio out back.

LocationFamilyAccuracy

The front exterior of the home features vibrant, blooming flowerbeds with a variety of blue and pink flowers. Two hanging planters with yellow flowers adorn the entryway, while a charming red door stands out against the yellow walls. A small seating area with dark chairs is visible on the porch.

5.0 out of 5 average rating, 200 reviews

Historic & sunny home steps from USNA/downtown

This beautiful and cozy 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City Dock and Gate 1 (main gate) of the US Naval Academy. Filled with sunlit, spacious rooms and equipped with numerous amenities (incl. gas fireplace), this home can sleep up to 8 (on 4 beds in the 3 bedrooms and 1 futon in a private room in the basement) and offers a combination of location and charm that is hard to beat!

ValueFamilyBarbecue

4.97 out of 5 average rating, 109 reviews

A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.

Home in Shady Side

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

FamilyLocationWi-Fi

A tranquil bedroom features a spacious bed adorned with a patterned throw and neatly arranged pillows. A modern lamp and decorative mirror enhance the ambiance, while natural light enters through a unique shaped window. A soft towel is elegantly rolled on the bed.

4.94 out of 5 average rating, 202 reviews

The Navy House-Walk or Shuttle Downtown! 3 bd

Your family will be close to everything when you stay at this centrally-located home. 3 blocks from the Navy stadium and walking distance to amazing restaurants! Here is your Annapolis home away from home. Our 3 bedroom 2.5 bath bungalow retreat is perfect for 6-7 people wanting to relax and see all that beautiful Annapolis has to offer. There’s also a free shuttle that takes you downtown to the water. Come, enjoy!

ValueLocationBathroom

Popular amenities for Annapolis house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 126 reviews

The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.

Home in Stevensville

Beautiful Kent Island Getaway with Pool

LocationFamilyBeach

5.0 out of 5 average rating, 325 reviews

The outdoor area features a circular pool surrounded by colorful lounge chairs in yellow, blue, and white. Umbrellas in red and blue provide shade over a dining table with red chairs. Towering trees frame the view of the expansive waterfront beyond.

Home in Kent Narrows

Chester Riverfront At Kent Narrows

FamilyLocationAir conditioning

4.86 out of 5 average rating, 221 reviews

A large, two-story home with a welcoming front porch is set amidst a spacious green lawn. The house features a grey exterior with white trim and multiple windows, surrounded by trees and landscaping, creating a peaceful and private atmosphere.

Home in Severn

Large Home with Private Pool, Gym, Sauna, 7 Bedroo

ValueFamilySleep quality

4.99 out of 5 average rating, 247 reviews

A spacious living area features two comfortable sofas, one draped with a soft blanket. Natural light streams through large windows, highlighting the wooden flooring. A small wooden table is visible in the background, and a decorative piece hangs above the mantel.

Home in Tracys Landing

The Little Gypsy BoHome

ValueFamilyView

4.87 out of 5 average rating, 114 reviews

Home in Waldorf

*Brand New | Modern Farmhouse | Lux 4 BR | Near DC

ValueFamilyAccuracy

4.9 out of 5 average rating, 223 reviews

Home in Fort Washington

Inground Pool | Hot Tub | Sauna | Theme Room

FamilyLocationIndoor spaces

4.97 out of 5 average rating, 295 reviews

A cozy living area features comfortable seating on a light grey sofa and a matching love seat. A coffee table is centered on a warm wooden floor, and natural light flows in through glass doors leading to the outside. A wall-mounted TV and artwork enhance the space.

Home in St. Michaels

Miles Aweigh

FamilyValueAccess

4.82 out of 5 average rating, 170 reviews

A winding stone pathway leads through a vast green lawn towards the shimmering waters of the eastern Chesapeake Bay. Two comfortable lounge chairs are positioned at the water's edge, offering a serene view of the horizon under a soft blue sky.

Home in Queenstown

Bay Breeze Retreat

FamilyLocationView

Weekly house rentals

The historic home is framed by vibrant trees, with its white exterior accented by red shutters. A white picket fence encloses the front yard, creating a charming and inviting entrance. Subtle shadows play across the facade, enhancing the seasonal beauty.

4.99 out of 5 average rating, 165 reviews

Crab Cakes and Football Historic District

LocationFamilyOutdoor spaces

4.91 out of 5 average rating, 143 reviews

An open layout living area features a kitchen equipped with stainless steel appliances and a breakfast bar with high stools. A dining table is visible in the background near large windows. The space is complemented by two leather couches and light hardwood flooring.

Home in Arnold

Rachel's BnB

FamilyLocationAmenities

An inviting front yard is presented, featuring a pathway of round stones leading to the entrance of a two-story guesthouse. Lush greenery is framed by ornamental plants and mulched beds, creating a serene outdoor setting surrounded by trees.

4.98 out of 5 average rating, 188 reviews

Quiet Waterfront

FamilyLocationPool

An inviting living room showcases a light-colored sectional sofa adorned with decorative pillows. A wooden coffee table, accompanied by a small ottoman, sits on warm hardwood flooring. Natural light filters through the window near the front door, which features glass panels.

4.92 out of 5 average rating, 367 reviews

Cozy 2br home w/ parking in downtown Annapolis

FamilyValueNearby

The front porch features a welcoming red door and blue Adirondack chairs. Stone steps lead to the porch, adorned with a large pot of yellow flowers and a matching red planter. White railings frame the porch, enhancing its charming appearance.

4.99 out of 5 average rating, 185 reviews

Charming house; walk to everywhere in Annapolis

ValueLocationIndoor spaces

4.95 out of 5 average rating, 104 reviews

USNA downtown house with garage parking EV 3bd/2ba

LocationFamilyNearby

A newly renovated home is presented with light grey siding and blue accents. Two spacious decks with white railings create inviting outdoor spaces. Flower beds with blooming plants enhance the entryway, while leafy trees provide shaded areas around the property.

4.98 out of 5 average rating, 106 reviews

Captain’s Retreat! Newly Renovated - Beach House!

LocationFamilyAmenities

A modern kitchen features a large marble island with seating for several guests. White cabinetry and a stainless steel stove create a clean aesthetic. Natural light filters in through multiple windows, illuminating the thoughtful decor, including a chandelier and a vase with fresh flowers on the island.

4.98 out of 5 average rating, 158 reviews

Gorgeous Historic Downtown Annapolis House

LocationValueComfort

Private house rentals

A spacious bedroom features a cozy bed with neutral-toned bedding and decorative pillows. Natural light fills the room through large windows, revealing views of the garden outside. A bedside table and a lamp complement the inviting space, with soft carpeting underfoot.

4.96 out of 5 average rating, 77 reviews

CJ's Cottage

LocationFamilyIndoor spaces

The screened porch is illuminated by soft lighting, featuring comfortable seating and a dining table. Large windows provide a view of the interior space, while a pathway leads to the entrance. The wooded surroundings create a serene backdrop for outdoor enjoyment.

4.99 out of 5 average rating, 68 reviews

Annapolis Cottage at Bay Ridge, Renovated

FamilyLocationBeach

The living room features a curved teal sectional sofa, a light wooden coffee table, and a beige accent chair. Artwork is displayed on the wall above the sofa. A soft area rug adds warmth, and natural light is present from an unseen window.

5.0 out of 5 average rating, 33 reviews

Newly Renovated Downtown Charm, Game Room, Patio

ValueFamilyCheck-in

A spacious living area features a custom stone fireplace, surrounded by soft seating and a rustic coffee table. Large glass doors provide views of the outdoor space. A ceiling fan adds to the comfortable ambiance, while a large clock adorns the wall.

5.0 out of 5 average rating, 29 reviews

Marymont Cottage

FamilyLocationOutdoor spaces

The exterior of a charming, single-story house is depicted, featuring a well-maintained lawn bordered by trees and shrubs. A vibrant red door provides a welcoming focal point. The pathway leads to the entrance, complemented by stairs on either side, indicating accessibility.

5.0 out of 5 average rating, 36 reviews

The Red Door Cottage - Pet-Friendly!

LocationFamilyComfort

5.0 out of 5 average rating, 47 reviews

A sunlit sunroom features three comfortable armchairs arranged around a small table, offering expansive views of the water through large glass windows. Natural light floods the space, accentuating the serene atmosphere in this inviting seating area.

Home in Bozman

The Cottage at Broad Creek

LocationKitchenBathroom

The entryway features a vibrant red door framed by large windows, allowing natural light to fill the space. A stone pathway leads to the door, with a clean, well-maintained sidewalk visible. The surrounding area includes a tree and nearby steps up to an upper level.

4.94 out of 5 average rating, 32 reviews

Cozy Stay in Downtown Naptown

LocationValueSleep quality

A bright living area features a dark leather sofa and a cozy chair, complemented by a geometric area rug. Large windows provide natural light, while a flat-screen TV is mounted on the wall. A round coffee table holds magazines, creating an inviting space for relaxation.