Holiday rentals in Annapolis

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Top-rated holiday rentals in Annapolis

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The loft bedroom features a king-sized bed dressed in dark bedding and a textured throw blanket. Bedside tables with lamps flank the bed, and a decorative wall sign above adds a personal touch. A woven area rug is placed underneath, enhancing the cozy atmosphere.
Barn in Caledonia
4.94 out of 5 average rating, 101 reviews

The Loft+Silo+Hallmark movie town+Cozy+State Parks

Plan a memorable stay in an unforgettable location at our creek side silo that was once used on a farm in Arkansas to store grains and crops. This quiet, peaceful country setting is all within a short driving distance of state parks, hiking/biking trails, and historic Caledonia which offers quaint shops and fun events. Sunset at the Silos lives up to its name with views of sunsets, pastures of cattle, and if you're lucky deer! The silo may be just 24 feet across, but everything you need is here!

Guest favourite
The exterior of Posey's Place features a charming log cabin with a red metal roof. A welcoming sign announces the property, surrounded by lush greenery and flowering plants. The cabin is set back from the road, offering a tranquil rural aesthetic.
Cabin in Annapolis
4.92 out of 5 average rating, 39 reviews

Posey's Place - Secluded Log Cabin

**Updated wood flooring has been put in and all carpet removed! Secluded Log Cabin on working farm. Located in rural Iron County just minutes from Black River, St. Francois River, Clearwater Lake, Elephant Rocks, Johnson Shut-Ins, & Shepherd Mt. Bike Park. Located just 11 miles from either K Bridge or Sam A. Baker Park, crystal clear water is waiting for you just minutes away. Take a relaxing float and return to the cabin for smores around the fire pit. Come and sit a spell at Posey's Place!

Top guest favourite
An aerial view captures the carriage house with a spacious deck and an umbrella-covered table, complemented by decorative shrubs lining the property. The driveway accommodates multiple vehicles, while a flag adds a touch of charm to the inviting exterior.
Home in Farmington
4.97 out of 5 average rating, 113 reviews

Columbia Street Carriage House

Located in historic downtown Farmington, minutes away from restaurants, wineries, shops, and parks. Our newly renovated carriage house has much to offer! Our 2+ acre yard is fully fenced with a gated entrance offering privacy, a fire pit, covered patio, and large deck. The city park is located next door with a private acces gate offering basketball courts, pickle ball, tennis, swing sets, pavilions and playgrounds. Come enjoy a relaxing weekend or stay a week exploring the area attractions.

Guest favourite
A charming red cabin is nestled among vibrant green trees, with a small, clear creek flowing gently nearby. The natural setting is complemented by lush foliage, creating a peaceful retreat in a rural environment.
Tiny home in Annapolis
4.94 out of 5 average rating, 65 reviews

Cabin on the creek - Glamping & Black River floats

This is a great place to unwind and unplug. Enjoy the sights and sounds of the creek flowing right in front of the cabin. This is a small cabin with 4 beds (2 bunkbeds) and full bathroom. The front porch overlooks the creek. The outdoor area includes a gazebbo, propane grill, table and firepit. Enjoy exploring the creek. The area is close to multiple outdoor gems including the Black River, Taum Sauk Mountain, Sam Baker State Park. There is no kitchen, but there is a mini-fridge and microwave.

Top guest favourite
A serene bedroom showcases a spacious bed layered with soft linens and decorative pillows. Two bedside lamps provide warm illumination, complemented by artwork depicting mountains on the wall. Natural light filters through a set of large windows, framed by dark curtains, enhancing the calm atmosphere.
Bungalow in Ironton
4.98 out of 5 average rating, 51 reviews

Main Street Retreat, walk to downtown Ironton

Welcome to Mainstreet Retreat, this two bedroom bungalow is nestled a few blocks from the town square of Ironton. There are several shops and restaurants in close proximity, the home features a covered front porch to enjoy mountain views, the bathroom has recently been updated! This home has a patio in the back, with a stainless steel firepit, off street parking, the property is only a short drive away from several of the state parks around the area, Elephant Rocks being about 5 minutes away!

Superhost
A charming log cabin is set amidst lush trees, featuring a green metal roof and a welcoming porch. Stone pathways guide to an outdoor seating area with a picnic table, complemented by a fire pit surrounded by natural stones, creating an inviting outdoor environment.
Cabin in Lesterville Township
4.87 out of 5 average rating, 347 reviews

Black River Cozy Cabin

This quaint cozy cabin offers a retreat from life's hustle and bustle with breathtaking views and a serene environment. The Black River Cozy Cabin is perfect for family vacations or a romantic get-away. With a secluded lake out the back door and two fire pits for roasting marshmallows and hot dogs, there are plenty of outdoor activities without even leaving the property. Of course, there is always more to explore in the area as well; including the Black River, which is just a short hike away.

Guest favourite
A 20-foot yurt is situated among bare trees, surrounded by nature. A spacious wrap-around deck enhances outdoor living. The structure features a circular design with a clear dome top and a single door visible. Nearby, a separate area can be seen, possibly for cooking or relaxation.
Yurt in Fredericktown
4.91 out of 5 average rating, 105 reviews

St Francis River: The Blue Yurt and Hot Tub

Let your adventure begin inside the tranquil experience of this 20 ft yurt. Don't let the space fool you, the uniquely curved walls give ample space for a romantic getaway or a relaxing time with friends. The clear dome top provides a magical viewing experience from the queen size bed. The yurt is nestled in the heart of the Ozark Mountains. The expansive, romantically lighted, wrap-around deck provides a panoramic view of the St. Francis River where you can immerse yourself in the hot tub.

Top guest favourite
Treehouse in Greenville
5 out of 5 average rating, 322 reviews

Private HOT TUB "The Roost" A Secluded Treehouse

"The Roost" is a modern treehouse 2 hrs south of St Louis near Wappapello Lake. Yes it has indoor plumbing & running water. Accommodates two adults, has a fully equipped kitchen, and breakfast items are provided for you to cook. Surrounded by thousands of acres of national forest. Observe wildlife sightings from the deck while soaking in the private hot tub, sleep comfortably in a queen size pillowtop Serta bed on a Motion Air base, and relax as you enjoy the ambience of the fireplace.

Top guest favourite
A modern cabin exterior is framed by a vibrant landscape. Light-colored siding is contrasted with a dark roof, and the entrance features a welcoming porch supported by wooden beams. Potted flowers add a touch of color, while windows allow natural light to fill the interior.
Cabin in Piedmont
5 out of 5 average rating, 68 reviews

By Clearwater Lake/Black River-Golf Range On-Site

One bedroom cabin loaded with amenities! Private location in a 12 acre field with wildlife to watch and also conveniently located a few blocks from Main Street. NO EXTRA FEES ADDED/no household chores! Free parking, plenty for boats and atv’s also No amenities left out-laundry facilities, all cooking supplies, stocked coffee bar, high speed internet, Netflix, plush king bed, rainfall shower head and more. Please note: a silicone heat pad is provided for all irons in the bathroom.

Top guest favourite
Several alpacas are gathered in a sunny pasture, showcasing their soft, fluffy coats. The group includes a variety of colors, from creamy white to rich brown, with their distinctive faces and calm expressions visible. A fenced area and grassy landscape are seen in the background.
Farm stay in Arcadia
4.93 out of 5 average rating, 141 reviews

Alpaca Farm Stay (save 10% for non-refundable)

Come see the baby alpacas and stay at the most tranquil and private getaway retreat in Arcadia Valley, Missouri and reconnect with nature. Our alpaca farm is nestled on over 28 acres in the Saint Francois Mountains next to the Mark Twain Natl Forest. The lodge is the perfect place for fishing on our 4-acre lake, relaxing after a long day of hiking, and meeting a small herd of alpaca. Your group will have an opportunity for a one-hour meet-and-greet scheduled at your convenience.

Top guest favourite
Tiny home in Patterson
4.89 out of 5 average rating, 19 reviews

Rustic Tiny Home

Get away from it all when you stay under the stars. This sweet little accommodation is rustic on the inside and nestled in the Missouri Southeast close to the historic Sam A. Baker State Park. Two full hook up RV sites are on either side of the tiny home, allowing for camping of family or friends. Your host is close by in a home next door allowing us to quickly meet needs that may surface during your stay. The unit does have a washer/dryer as well. Note: RV rental is separate.

Guest favourite
Cabin in Ironton
5 out of 5 average rating, 7 reviews

The Tiegen Rae: cozy mountain cabin w/ huge views

Take it easy at this unique and tranquil getaway. "The Tiegen" is a beautiful A-frame cabin sitting on 20 acres at the top of Anderson Mountain. Imagine drinking your morning coffee sitting in a rocking chair and enjoying the breathtaking view of the Mark Twain National Forest. Or picture lighting an evening fire to enjoy the sounds of the woods with your favorite drink. This cabin will not disappoint and boasts full amenities to go along with your glamping adventure.

Popular amenities for Annapolis holiday rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Iron County
  5. Annapolis