Vacation rentals in Annapolis

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Top-rated vacation rentals in Annapolis

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Guest favorite

Home in Fredericktown

4.94 out of 5 average rating, 180 reviews

Outdoor Heart BathTub The Rustic Rose River Access

The Rustic Rose is one of 7 uniquely themed stays on our small private family ran campground. It’s a short 5 minute walk through the property trails to crystal clear river -12Mile Creek just south of Fredericktown, MO. You will have 33 acres to explore, with refreshing swimming holes, shut-ins, bluffs, fishing, wooded trails and more than enough nature to bask in. Deer, rabbits, turtles & many different species of birds too! The unique old Vegas style, whimsical décor makes for a memorable stay!

Aug 9 – 16

G$31,904 GYD per night

Guest favorite

Treehouse in Greenville

5.0 out of 5 average rating, 143 reviews

NEW treehouse B&B for 2 "The Roost” with hot tub

Cozy 2022 custom rustic but not primitive cabin 2 hours south of St Louis MO (our zip 63944) Yes it has indoor plumbing and 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 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.

Aug 13 – 20

G$36,466 GYD per night

Guest favorite

Farm stay in Fredericktown

4.96 out of 5 average rating, 142 reviews

Spring Valley Ranch Rock House

This quaint farmhouse is located just off of MO Hwy 72 on a 62 acre farm nestled against the Castor River. Here you and your companion(s) can experience the quiet and relaxing life on a farm with plenty of adventure awaiting just around the bend. Sit and enjoy a sip of coffee or tea on the front porch while watching the cattle graze the pasture across the road next to a rustic white barn or venture about 3 miles to the largest privately owned lake in Madison County. Oh yes, enjoy your stay!

Jun 6 – 13

G$24,948 GYD per night

Superhost

Cabin in Lesterville Township

4.87 out of 5 average rating, 252 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.

Mar 1 – 8

G$29,979 GYD per night

Guest favorite

Farm stay in Arcadia

4.91 out of 5 average rating, 115 reviews

Alpaca Farm Stay

Come 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 family and spouse will love feeding the alpacas as all guests will have a one-hour meet-and-greet scheduled at your convenience.

Feb 13 – 20

G$28,960 GYD per night

Guest favorite

Tiny home in Annapolis

4.94 out of 5 average rating, 36 reviews

Charming cabin on the creek

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 propane grill, picnic 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.

May 28 – Jun 4

G$17,673 GYD per night

Guest favorite

Apartment in Van Buren

5.0 out of 5 average rating, 158 reviews

The Bonney House BnB

Current River retreat one bedroom open concept apartment w/ kitchenette. It has a gas fireplace & 55" TV. The kitchenette has microwave oven, coffee pot w/ filters & coffee, electric skillet, fridge w/ icemaker and basic dishes. The bathroom has a shower only. Apt has covered patio with outdoor dining & gas grill. You have access to wood firepit w/seating & picnic table. There's also a pavilion w/gas firepit & table w/seating overlooking Current River Bay. No smoking in apt. No pets.

May 7 – 14

G$23,901 GYD per night

Guest favorite

Cabin in Ironton

5.0 out of 5 average rating, 103 reviews

The Valley Getaway Cabin:

Welcome to the most private getaway retreat in the beautiful Arcadia Valley, MO. Settled on 80 acres of wildlife and walking trails. The cabin is the perfect place to enjoy a long day of fishing and end the day with a relaxing bonfire with friends and family. To go along with the many activities to do while staying at the cabin, there are also many things to enjoy just a few miles away. From visiting elephant rocks for a peaceful walk to visiting the famous Shepard mountain bike trail.

Jul 20 – 27

G$40,126 GYD per night

Guest favorite

Home in Lesterville

4.86 out of 5 average rating, 119 reviews

Black River Dobbins House & Pavilion, Lesterville

This one of a kind historic home is located in the heart of Lesterville within walking distance to the local stores and restaurants. Included with stay is a private pavilion located on the crystal clear Black River less than a mile away. If floating of any kind is on your agenda, free shuttle to the house is available from some of the local campgrounds when you use them to navigate the black river. This home is just minutes away from Johnson's Shut Ins State Park and Elephant Rocks.

Sep 24 – Oct 1

G$37,889 GYD per night

Guest favorite

Cabin in Annapolis

4.8 out of 5 average rating, 25 reviews

Panther Den Cabin is found 4 mile from K Bridge

The Panther Den is a brand new Cabin that is only 4 miles for Black River and Hwy K Campground. Cabin has two lofts for sleeping that kids will love!! Annapolis, Missouri is in the middle of tons of attractions and places to visit. Johnson's Shut-Ins State Park, Elephant State Park, Taum Sauk State Park and Sam A. Baker State Park are all within 30 minutes. Wappappello and Clearwater Lake are a short drive as well. Fire pit, BBQ grill, and picnic table comes with the Cabin.

Mar 8 – 15

G$25,185 GYD per night

Guest favorite

Cabin in Arcadia

4.98 out of 5 average rating, 62 reviews

Quaint Little Porch Cottage

This wonderful little cabin is perfect for the couple that wants to get away. With its amazing screened in porch, it's the perfect place to have your morning coffee and watch the wildlife or a nice glass of wine at night. Sitting on 38 gated acres, this cabin shares the property with 6 other rentable cabins. This property adjoins our 700-acre property where we have a stocked pond for your fishing enjoyment and 6 miles of hiking/horse riding trails through our rolling woods.

Jun 9 – 16

G$24,057 GYD per night

Guest favorite

Home in Piedmont

4.96 out of 5 average rating, 23 reviews

Clearwater Lake Red Roof Cabin

Located less than 1 mile from Clearwater Lake Marina, swim area, playgrounds, and spillway, this newly renovated cabin has everything you need to kick back, relax, and unwind. This one-bedroom cozy cabin features new appliances, a washer/dryer, a coffee maker, and a stocked kitchen to make you feel at home. We are now offering WI-FI! There is also a DVD player, DVDs, chargers and Bluetooth speaker, board games, cards, and children's books.

Dec 13 – 20

G$34,339 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Annapolis vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Annapolis

Guest favorite

Home in Piedmont

5.0 out of 5 average rating, 18 reviews

The Yellow House at Bluffview ~ .5 mile from lake

Jan 2 – 9

G$27,249 GYD per night

Guest favorite

Cabin in Patterson

4.89 out of 5 average rating, 9 reviews

Lakeview Cabin With Hot Tub

May 9 – 16

G$33,477 GYD per night

Guest favorite

Home in Ironton

4.96 out of 5 average rating, 78 reviews

3 Bedroom Gem in the Heart of Ironton

Jan 7 – 14

G$27,747 GYD per night

Superhost

Castle in Ironton

4.97 out of 5 average rating, 32 reviews

Historic Goulding Castle circa 1846

Sep 15 – 22

G$84,938 GYD per night

Superhost

Cabin in Lesterville

4.82 out of 5 average rating, 68 reviews

R & S Cabin on the beautiful black river.

Feb 17 – 24

G$36,086 GYD per night

Guest favorite

Home in Lesterville

4.93 out of 5 average rating, 61 reviews

The Black River Oasis on the Middle Fork

Jan 25 – Feb 1

G$62,978 GYD per night

Guest favorite

Farm stay in Arcadia

4.95 out of 5 average rating, 43 reviews

Elephant Rocks cabin at The Maples

Jun 24 – Jul 1

G$26,671 GYD per night

Guest favorite

Cottage in Marquand

4.87 out of 5 average rating, 45 reviews

Country Retreat

Feb 24 – Mar 3

G$26,828 GYD per night

Show all

Quick stats about vacation rentals in Annapolis

Total rentals	10 properties
Popular amenities	Gym, BBQ grill, and Laptop-friendly workspace
Wifi availability	10 properties include access to wifi
Pet-friendly rentals	10 properties allow pets
Total number of reviews	330 reviews
Nightly prices starting at	G$18,807 GYD before taxes and fees

Vacation rentals in Annapolis

Top-rated vacation rentals in Annapolis

Home in Fredericktown

Treehouse in Greenville

Farm stay in Fredericktown

Cabin in Lesterville Township

Farm stay in Arcadia

Tiny home in Annapolis

Apartment in Van Buren

Cabin in Ironton

Home in Lesterville

Cabin in Annapolis

Cabin in Arcadia

Home in Piedmont

Vacation rentals for every style

Cabins

Hotels

Unique stays

Popular amenities for Annapolis vacation rentals

Other great vacation rentals in Annapolis

Home in Piedmont

Cabin in Patterson

Home in Ironton

Castle in Ironton

Cabin in Lesterville

Home in Lesterville

Farm stay in Arcadia

Cottage in Marquand

Quick stats about vacation rentals in Annapolis

Total rentals

Popular amenities

Wifi availability

Pet-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore