Vacation rentals in Annapolis

4.96 out of 5 average rating, 649 reviews

Two lounge chairs are positioned on a wooden deck, surrounded by lush greenery. A wooden tray holding glasses and fresh fruits rests on the ground nearby, inviting relaxation in the tranquil outdoor setting.

Tiny home in Park Hills

🔝❤️ PEACEFUL TREETOP COTTAGE

KrystaRating, 5 stars4 days ago

Such a beautiful place and couple. Impeccable hosting. We felt very taken care of. We came for a staycation for my fiancés’ birthday and were warmly welcomed and taken care of. Thank you for the amazing stay! We look forward to coming back.

Cabin in Black River Township

A covered patio features a dining table with cushioned chairs under a white umbrella. Potted plants and the cabin’s vibrant entrance are visible, surrounded by trees that create a serene outdoor setting. Natural light filters through, enhancing the inviting atmosphere.

4.99 out of 5 average rating, 70 reviews

Well-Designed Wooded Cabin near lake and hiking

CarolRating, 5 stars3 weeks ago

If you are seeking peace and a quiet surroundings, this is the place to stay. There are lakes and lots of areas to hike. The kitchen is stocked with the equipment for some serious cooking and there is a grill and a firepit outside. The internet service is fast, the cable service has plenty to watch and the cabin is stocked with board games. If you are looking for lots of restaurants and high end grocery stores, this is probably not the best area for you.

4.9 out of 5 average rating, 286 reviews

The riverbank is framed by tall trees with lush green foliage, providing natural shade. A wooden walkway leads to the water's edge, where the calm river reflects the surrounding vegetation, creating a serene outdoor setting. A peaceful spot for relaxation is visible along the bank.

Cabin in Fredericktown

Hot tub/ Blissful Beaver River Cabin

NicholasRating, 5 stars3 months ago

Amazing little cabin on the St. Francis River! We enjoyed our little NYE winter getaway. The hot tub made the winter all the more enjoyable and relaxing. The beds were comfy and the kitchen was stocked w everything we needed to cook various meals. Misty was very friendly and easy to communicate with. We would love to come back again when the weather is warmer out!

5 out of 5 average rating, 5 reviews

A rustic treehouse stands above a gently flowing creek, framed by bare trees. The building features large windows that reflect the surrounding landscape, showcasing its harmonious connection to nature. A serene ambiance is created by the calm water and earthy tones of the setting.

Treehouse in Marble Hill

Crooked Creek Treehouses (Stony Branch Loft)

TaraRating, 5 stars1 week ago

My husband and I celebrated our 17th wedding anniversary with an amazingly peaceful stay! We arrived to the cutest welcome sign wishing us a “Happy Anniversary” along with celebratory drinks. There was absolutely everything we needed and more! We met Roger when he checked in to see if we needed anything! Barb was always very quick to respond and overly helpful! We have already started making plans for our return hopefully next year! Thanks again ❤️

4.96 out of 5 average rating, 117 reviews

A welcoming front porch features two light green chairs and a small table, framed by a white railing. Outdoor string lights are hung overhead, providing soft illumination. Windows with multiple panes offer views into the cozy interior space.

Bungalow in Ironton

*Downtown Bungalow*Coffee Bar*Pet*Family Friendly*

MarcRating, 5 stars1 month ago

This clean and welcoming bungalow sit in a quiet little town it is a short drive from so many outdoor activities! The friendly residents of Ironton were generous with advice about off the beaten path excursions and a little known gems. Just stop in the local coffee shop or one of the local delis or restaurants and tell them that you are in town for outdoor fun. Good grocery options within walking distance made cooking in the nice kitchen at the bungalow and option for staying in and saving money some nights. The hosts were very responsive to needs, and the accommodations exceeded our expectations. The coffee bar was a real highlight!

4.8 out of 5 average rating, 54 reviews

Home in Bonne Terre

PEACEFUl home w/ Trails, Rolling hills & Lakeside

RonaldRating, 5 stars1 month ago

The house and property are beautiful and very private. The back porch was a great location to watch the sunsets. Also, kitchen now a microwave which was a bonus since previous comments talked about no microwave. Our phones connected to 5G so the fact that there was no a TV or wifi wasn't an issue for us. The beds were comfortable and everything was clean. The house is about 30-40 minutes (or less) from 3-4 state parks. Would definitely stay again!

5 out of 5 average rating, 33 reviews

Cabin in Van Buren

Private Hilltop Cabin Near Current River

KatelynRating, 5 stars1 day ago

Lenice and Kody very accommodating. The home was very beautiful very clean. It was accommodating. Lynsey was so sweet. Every time I worked with her she was kind responding quickly to us. Let us have an early check-in because it was raining on us and all of our luggage, they are just wonderful people. You’d be very blessed to stay in their home

4.94 out of 5 average rating, 17 reviews

A wooden sign displaying the text 'Cozy Corner' is mounted on a dark exterior wall. The sign features a simple graphic of a house and an arrow that points to the right, indicating direction.

Apartment in Van Buren

Cozy Corner

AngelaRating, 5 stars9 months ago

Just what we were looking for in a low key weekend getaway! Natalie was a great host, and very helpful from before checking in when GPS was messing up on our end and we needed a pin dropped, answering any questions we had quickly, and having clear instructions for checking and checkout.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

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Popular amenities for Annapolis vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Annapolis

4.96 out of 5 average rating, 75 reviews

Home in Poplar Bluff

6 Bed 2 Bath Home in Quiet Neighborhood - Sleeps 9

DerekRating, 5 stars4 weeks ago

Great stay in a good location. House was as described and very clean. Best stay that we have had in Poplar Bluff.

4.96 out of 5 average rating, 648 reviews

The outdoor patio features a black metal table and chairs, surrounded by potted colorful plants. Natural light fills the area, showcasing a serene view of the water and the lush green landscape beyond. The rustic cottage design adds charm to this relaxing outdoor space.

Cabin in Bonne Terre

The Waterfront cottage

DaneRating, 5 stars2 weeks ago

This place was a great getaway from the business of every day life. Host was very responsive, and we would 10/10 stay again. The bathtub on the deck is a great feature after dark, and it’s so quiet and peaceful. Lots of games supplied and the loft is an awesome little nook. The 2PM check in is an awesome addition to get your getaway started early. Almost like having another day

5 out of 5 average rating, 70 reviews

The spacious living area is designed with wooden features and a stone fireplace, creating a rustic ambiance. A large sectional sofa, decorated with vibrant pillows, surrounds a unique, natural wood coffee table. Natural light streams through large windows, illuminating the warm tones of the space.

Home in Ste. Genevieve

Secluded Private Cabin with Pool, hot tub, firepla

EmmaRating, 5 stars1 week ago

This property exceeds 5 stars without a doubt - our only complaint is that we didn’t plan to stay longer!!! We were stopping through on a 5,000 mile road trip & it was like a spot of sheer relaxation & amazingness with something for everyone. The meticulousness of the property was amazing - from the helpful labels to the abundance of towels (for outside & inside) - this property exceeds allll expectations.

Vacation home in Eminence

4.95 out of 5 average rating, 20 reviews

Pet friendly Beautiful 4 bedroom home in eminence

PhillipRating, 5 stars8 months ago

Enjoyed being walking distance too town. And ending our float right by house was nice

5 out of 5 average rating, 7 reviews

A spacious wooden deck overlooks a serene river, decorated with an American flag. A dining set with several chairs is positioned for outdoor meals, surrounded by lush greenery and a clear blue sky dotted with clouds.

Cabin in Van Buren

Wagnon's Landing

KristenRating, 5 stars1 month ago

Our family had a wonderful stay at the house. The kitchen was so well stocked, best I’ve seen at a rental house. The location is beautiful, views of the river from the house are amazing. We would definitely stay again!

5 out of 5 average rating, 4 reviews

A clear, tranquil body of water is surrounded by rocky terrain and lush greenery. The water reflects a deep blue hue, transitioning to lighter shades near the sandy shore. Sunlight penetrates the scene, enhancing the natural beauty of the landscape.

Home in Annapolis

3 bedroom 2.5 bath

DaveRating, 5 stars6 months ago

Lucy was very communicative abouts the house and activities and attractions nearby. She was very responsive. The house worked very well for our family of 5 with the three baths and two full showers. Nice deck off the back of the house with a couch, table and umbrella and gas grill. We really enjoyed the nice fire pit and big yard and my kids loved the cows right across the street!

4.91 out of 5 average rating, 11 reviews

A well-maintained green lawn is illuminated by string lights, creating a welcoming ambiance. To the left, a rustic cabin stands near the lawn, while a spacious barn is visible in the background. The setting sun casts a warm glow over the landscape.

Farm stay in Davisville

Pine Valley at Dillard Mill - The Farm

JasonRating, 5 stars8 months ago

This place is amazing and we definitely want to come back. Jay was very hospitable and responsive. As others mentioned in their reviews, the professional kitchen in the common area really is great. We came down to Pine Valley with a big group for a float trip. Its was a huge relief that this property had everything we needed and more so we could just focus on spending time with each other. Oh, and we found a full size cornhole game with sandbags we played with too. Fun.