House vacation rentals in Annapolis

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Popular amenities for Annapolis house rentals

House rentals with a pool

Superhost
A refreshing saltwater pool is framed by comfortable lounge chairs in vibrant red and blue. A large grassy area is visible beyond the pool, leading to serene waterfront views under a clear blue sky, complemented by a tree providing shade.
Home in Queenstown
4.81 out of 5 average rating, 157 reviews

Bay Breeze Retreat

TobyRating, 5 stars2 weeks ago
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.
Guest favorite
The exterior view showcases a spacious backyard with an inviting swimming pool surrounded by lounge chairs and blue umbrellas. A two-story gray house stands prominently, with a deck and seating area visible, all framed by greenery and a clear sky.
Home in Cambridge
4.97 out of 5 average rating, 115 reviews

Gorgeous, waterfront home - Perfect for Families.

DavidRating, 5 stars1 week ago
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.
Guest favorite
The large in-ground pool is surrounded by a spacious patio, offering multiple lounge chairs for relaxation. A vibrant red umbrella provides shade in one corner, while lush greenery and flowering bushes frame the area, creating a private and serene outdoor atmosphere.
Home in Severn
4.88 out of 5 average rating, 169 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

SamihahRating, 5 stars6 days ago
This home was the perfect place to celebrate my daughter’s graduation! We had family travel in from several states, and everyone felt comfortable and truly enjoyed the spacious layout. It was a bit too chilly to use the pool, but I’m already looking forward to booking this home again. I’ll definitely be a repeat renter!
Guest favorite
A charming neoclassical farmhouse is observed, set among leafy trees. A wide gravel driveway leads to the welcoming front porch, which features white columns. Lush greenery surrounds the home, enhancing the tranquil setting of the property.
Home in Chester
4.95 out of 5 average rating, 95 reviews

Waterfront Farmhouse Meets Modern Luxury

TrishRating, 5 stars1 week ago
The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.
Superhost
A heated pool is set by the water's edge, reflecting blue skies and surrounding trees. A wooden deck features picnic tables and a large umbrella, with a private pier visible in the distance along the water. Adirondack chairs invite relaxation.
Home in Edgewater
4.82 out of 5 average rating, 22 reviews

South River Beach Front House

Katherine Rating, 5 stars3 weeks ago
I stayed here the week of my wedding and it was absolutely perfect! From waking up each morning to have coffee on the dock with my pups and husband, to the beautiful views from each room in the house, we truly had a lovely time and chose the right Airbnb for such a special week in our lives.
Top guest favorite
Home in Perry Hall
4.99 out of 5 average rating, 98 reviews

Gunpowder Retreat

AngieRating, 5 stars1 week ago
This house was perfect for our stay in MD. Our family of six was very comfortable here and our kids loved the pool and spa. The house is clean, cute and very cozy. Tanya was very quick to respond and great to work with!
Guest favorite
Home in Fort Washington
4.92 out of 5 average rating, 155 reviews

5 BEDR, Inground Pool+Billiard Table, Close To D.C

SantiRating, 5 stars2 weeks ago
This place is fantastic for a stay. Daniel is super communicative and quick to respond. Plus, the pool is impeccably clean.
Top guest favorite
A dining area features a glass-top table surrounded by rustic chairs. Sunlight filters through large windows, illuminating a vase of colorful flowers. The comfortable seating area, positioned by the windows, offers views of the bay, enhancing the tranquil ambiance.
Home in Tracys Landing
4.99 out of 5 average rating, 212 reviews

The Little Gypsy BoHome

Jane AnnRating, 5 stars1 week ago
Wonderful place - pictures do not do it justice. Home is spotless and beautifully furnished! We had a great time relaxing on our babymoon. Lots of great restaurants close by and so much to do at the house you never have to leave. Really appreciated the details such as the coloring station and ample beach towels. Hope to stay again in the future!

House rentals with free parking

Guest favorite
A lush green yard borders a calm body of water, where a private pier is visible. Flower beds with white and pink blooms add color to the scene. A small boat is moored at the pier, with trees providing shade along the waterfront.
Home in Annapolis
4.97 out of 5 average rating, 74 reviews

Annapolis USNA Cottage Waterfront Pier Cozy Escape

Nate And KatieRating, 5 stars2 weeks ago
Very quiet location but not far from amenities. The home had an attention to detail that not all air bnbs do (for example enough towel hooks for everyone staying!) as well as basic cooking amenities
Superhost
A cozy living room is featured with warm wooden paneling and a bright yellow front door. A comfortable sofa is complemented by a stylish chair and a decorative plant. A large map is displayed on the wall, adding a functional touch to the space.
Home in Annapolis
4.71 out of 5 average rating, 17 reviews

Wright's Cottage- Pet's Welcome & EV Charging

BethanyRating, 5 stars2 weeks ago
Danielle’s place was the perfect spot for a short getaway. While it’s on the smaller side, it was comfortable and worked out great for two people and our two dogs. We didn’t spend a ton of time indoors, but we loved relaxing by the outdoor fireplace in the evenings, such a nice touch! It’s about a 20-minute drive to downtown Annapolis, offering the best of both worlds: close to the city, but a peaceful escape from the hustle and bustle.
Top guest favorite
Home in Annapolis
5 out of 5 average rating, 38 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

Karina And ClintRating, 5 stars6 days ago
Gwen’s peaceful waterfront retreat was truly just that—peaceful and relaxing! From the moment we arrived, we felt welcomed and at home. Gwen was a gracious and responsive host, making sure everything was perfect for our stay. The property was filled with thoughtful touches and amenities that made our visit incredibly comfortable: a charming gazebo dining area, outdoor kitchen, a coffee bar, fresh flowers (such a lovely touch!), and more. The beds and bedding were comfortable, ensuring a great night’s sleep. The neighborhood is beautiful and quiet, with access to a private beach area that made the whole experience feel extra special. The highlight of our stay was undoubtedly the incredible dock experience—sitting right on the water, surrounded by nature, with comfortable chairs perfectly placed to enjoy morning coffee, afternoon sun, or stunning sunsets. Highly recommend for anyone looking to unwind in a serene waterfront setting!
Guest favorite
A modern two-story house features multiple large windows and balconies, allowing for ample natural light. The deck showcases orange lounge chairs positioned for outdoor relaxation, while the well-maintained lawn is bordered by trees displaying autumn colors.
Home in Deale
4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

CourtneyRating, 5 stars2 months ago
This air b&b is in a beautiful setting with plenty to do (kayaking, hot tub, fire pits, bird watching, etc). It's also very centrally located so we could easily get to more populated areas in no time. The most stunning part of the house is the master suite in my opinion which is on the upper level (the upper level is shared with another apartment, but you don't really hear the air b&b tenants of this suite and it's completely separate with a separate entrance). Stunning views from both the master bedroom and the bath tub in the master suite! The downstairs is also quite lovely with two regular bedrooms, one small bedroom, and a sun room that has a pull out couch (we didn't use it). It's a lovely house to entertain in. It has personal photographs to the owner downstairs that speak to the family's history. The owner is communicative. The overall experience was quite lovely. We'd be happy to return.
Top guest favorite
A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.
Home in North Beach
5 out of 5 average rating, 140 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton

AnnaRating, 5 stars2 weeks ago
We had the most amazing weekend. All of Kimberly’s recommendations were right on the money, and we were so impressed by the cleanliness, comfort and beauty of the home! Watching the sunrise over the water every morning from the front porch was heavenly!
Guest favorite
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
4.98 out of 5 average rating, 42 reviews

Rachel's BnB

WendyRating, 5 stars4 days ago
Above & beyond! The home was in a great spot with an excellent price. Tim was extremely accommodating with our requests and communication was perfect. The refrigerator was stocked with eggs and butter. The cupboards were stocked with staples and all the supplies we needed - toilet soap, shampoo, Kleenex, paper towels, bath towels, snacks, granola bars, etc. We would highly recommend this Airbnb to anyone and would use again. Thank you!
Top guest favorite
A dining area features a large wooden table surrounded by cross-back chairs. A light fixture with multiple bulbs hangs above the table. A sliding glass door opens to the deck, adorned with sheer curtains. Rustic decor, including a wine rack and lamp, enhances the inviting space.
Home in Annapolis
5 out of 5 average rating, 56 reviews

Downtown Annapolis Home

JessicaRating, 5 stars2 weeks ago
We booked Laura’s property 2 years in advance for Commissioning Week. Throughout the 2 years she answered our questions quickly and effectively. The house had room for 2 parents, 2 grandparents, and 1 sibling. Basement area is nice and private. The house looked just like the pictures. The driveway is hard to get out of during busy times, as it is on a roundabout. However, it was easily walkable to the stadium in less than 13 mins (perfect for graduation/commissioning week, as you have to pay for parking if you want to take the shuttle from the stadium to the yard). It is also walkable along West St, where all the shops and restaurants are. The furthest restaurant is 1 mile away, but there are many spots that are closer. It’s about 1.2 miles from Gate 1. You can take the free downtown shuttle that goes along West St if you don’t want to walk all the way. Overall a great place to stay when visiting a Midshipman or celebrating graduation!
Guest favorite
An aerial view showcases the stunning Heron House nestled on a waterfront point, surrounded by lush greenery and water. A spacious deck with outdoor seating and dining is visible, along with nearby boats docked along the shoreline under a twilight sky.
Home in Crownsville
4.93 out of 5 average rating, 14 reviews

Welcome to Heron House! Annapolis Waterfront Oasis

JenniferRating, 5 stars1 week ago
Very peaceful surroundings, you are out on a point overlooking the bay, with lots of outside space to relax in the mornings to enjoy your morning tea/coffee. I loved having the real fireplace and enjoyed an evening fire on the more chillier evenings. Felt at home and comfy.

Family-friendly house rentals

Superhost
A spacious bedroom features a large bed with a white quilted comforter and dark gray pillows. A wooden bench is positioned along one wall, and a small decorated tree stands nearby, providing soft lighting. The natural light enters through a large window with shades.
Home in Annapolis
4.73 out of 5 average rating, 122 reviews

West Annapolis SuperHost!

TimmyRating, 5 stars5 months ago
Perfect location if you’re in Annapolis for a game or just to visit the city. Christopher’s house was the perfect location and distance from everything in the city. Also, very spacious and nice house perfect for me and my 4 other friends.
Guest favorite
Home in Fells Point
4.89 out of 5 average rating, 104 reviews

Luxury Townhouse. Roof Deck. Patios & Parking

LindsayRating, 5 stars1 week ago
A gorgeous gem in the center of everything! Ally’s place is clean, comfortable, and beautifully decorated. We cooked several meals in the well-stocked kitchen, enjoyed time on the sunny patio, and walked to many amazing restaurants and shops. There were lots of thoughtful details - from the umbrella that helped out in a sudden rain storm to the labels on the light switches. Truly a gorgeous property in a prime location!
Top guest favorite
A single-story house is nestled among mature trees, featuring a welcoming front porch with steps leading to the entrance. The exterior displays a clean white facade, complemented by blue shutters and a brick chimney. A brick pathway winds through the landscaped yard.
Home in Glen Burnie
4.96 out of 5 average rating, 454 reviews

Secluded acre near BWI and Baltimore

JenRating, 5 stars4 days ago
What a beautiful little spot of heaven at the end of the long driveway nicely tucked back with orioles, bunnies and even two kitties running around outside, inside is the so quaint and comfy and clean. The view out the windows gave peace and the fireflies at night were so cool. Stanley went above and beyond to be accommodating on our trip and his place is top notch. 10/10 would stay again
Guest favorite
The exterior of a charming yellow house is featured, with a white railing enclosing a screened-in porch. Four wicker chairs are positioned on the porch, complemented by blue shutters on windows. A gated entrance provides access to the front yard, surrounded by greenery.
Home in Oxford
4.96 out of 5 average rating, 213 reviews

The Oxford House

GregRating, 5 stars6 days ago
This place is nicely furnished and the kitchen/dining area are very well supplied. We always enjoy our time in Oxford and the surrounding area and Suzanne Marie's place made it very comfortable. Walkable to the market, coffee shop, ice cream shop and 2 restaurants.
Guest favorite
A charming craftsman bungalow is surrounded by vibrant flower beds featuring colorful blooms. The entrance is highlighted by a spacious, covered porch supported by red pillars and white railing. Lush green grass and well-maintained landscaping enhance the inviting curb appeal.
Home in Hyattsville
4.92 out of 5 average rating, 239 reviews

Sunny, private apartment in historic neighborhood

Liz & TomRating, 5 stars3 weeks ago
This is a great place. Its sunny, easy to access, parking was great. The bed was very comfy. We had a good stay.
Top guest favorite
The master bedroom features a spacious bed with an elegant headboard, complemented by decorative wall accents and green plants. Soft light filters through sheer curtains, illuminating the wooden flooring and area rug. Nightstands with lamps are situated on either side of the bed.
Home in Millersville
4.98 out of 5 average rating, 150 reviews

BWI, Baltimore, Annapolis, DC, USNA - entire house

BrianRating, 5 stars2 weeks ago
Craig is a great host. Very proactive and responsive in his communication. His place was perfect for our group. Overall a great stay. Would definitely stay there again.
Superhost
A welcoming living area features a tan leather sofa adorned with patterned pillows. Two wooden coffee tables are centered on a textured area rug. Bright natural light streams in through a nearby doorway, while a green potted plant adds a touch of liveliness to the space.
Home in College Park
4.84 out of 5 average rating, 182 reviews

Spacious relaxing home by DC, CP, woods & lake

SusanRating, 5 stars1 week ago
We've stayed at Kopal's quite a few times - very peaceful neighborhood, very close to Lake Artemisia, which is lovely for walking, also very close to College Park. Great location. The house is always very clean, well-equipped and Kopal is so responsive.
Top guest favorite
An aerial view captures the expansive waterfront estate surrounded by lush greenery and a tranquil waterway. The pier extends towards the water, while the house is set back from the banks. Nearby structures include docks and quaint homes along the shoreline.
Home in Deale
4.99 out of 5 average rating, 144 reviews

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa

MelissaRating, 5 stars1 week ago
This was a beautiful waterfront home! This home was well equipped with everything you may need! The host was available if we needed anything! Would definitely recommend!

Quick stats about house rentals in Annapolis

  • Total rentals

    390 properties

  • Total number of reviews

    14K reviews

  • Family-friendly rentals

    340 properties are a good fit for families

  • Pet-friendly rentals

    130 properties allow pets

  • Rentals with dedicated workspaces

    230 properties have a dedicated workspace

  • Wifi availability

    390 properties include access to wifi

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