Vacation rentals in Annapolis

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Top-rated vacation rentals in Annapolis

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

Guest favourite
Treehouse in Greenville
NEW treehouse B&B for 2 "The Roost” with hot tub
Cozy new 2022 custom built rustic but not primitive cabin 2 hours south of St Louis MO. Yes it has indoor plumbing and running water. Accommodates two adults only, 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.
Feb. 7 – 14
$269 CAD per night
5.0 out of 5 average rating, 134 reviews
Guest favourite
Cabin in Lesterville Township
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.
May 30 – Jun. 6
$204 CAD per night
4.88 out of 5 average rating, 248 reviews
Guest favourite
Yurt in Boss
Entire private Glamping Yurt next to forest
Pet friendly glamping in 1 of 2 private yurts next to the Mark Twain National Forest, is the perfect place to escape! Relax to all the sounds of nature the Mark Twain National Forest has to offer. Take in the stunning 360° views & peaceful surroundings from the 30'X30' wraparound deck! Spend your days hiking, kayaking, & all the things the area has to offer & your evenings around the campfire, watching the sunset & star gazing. If you love camping & modern amenities, you will love this place.
Jul. 19 – 26
$160 CAD per night
4.96 out of 5 average rating, 115 reviews

Popular amenities for Annapolis vacation rentals

Other great vacation rentals in Annapolis

Superhost
Cabin in Lesterville
R & S Cabin on the beautiful black river.
Oct. 7 – 14
$261 CAD per night
4.82 out of 5 average rating, 68 reviews
Guest favourite
Home in Lesterville
The Black River Oasis on the Middle Fork
Aug. 15 – 22
$490 CAD per night
4.93 out of 5 average rating, 60 reviews
Guest favourite
Cabin in Arcadia
Quaint Little Porch Cottage
Jan. 5 – 12
$178 CAD per night
4.98 out of 5 average rating, 59 reviews
Guest favourite
Bungalow in Lesterville
FLOATING! Black River Bungalow (Lesterville, MO)
Jun. 7 – 14
$429 CAD per night
4.89 out of 5 average rating, 36 reviews
Guest favourite
Cabin in Ironton
The Valley Getaway Cabin:
Apr. 28 – May 5
$300 CAD per night
5.0 out of 5 average rating, 98 reviews
Guest favourite
Home in Van Buren
Luxury Log Cabin: 5 bedroom Van Buren River Cabin
Jan. 24 – 31
$554 CAD per night
5.0 out of 5 average rating, 34 reviews
Guest favourite
Home in Piedmont
Clearwater Lake Red Roof Cabin
Nov. 5 – 12
$224 CAD per night
4.95 out of 5 average rating, 21 reviews
Guest favourite
Cabin in Fredericktown
Cabin with a view
Aug. 16 – 23
$182 CAD per night
5.0 out of 5 average rating, 42 reviews
Guest favourite
Treehouse in Perryville
Rustic reTREEt Treehouse Getaway
Feb. 21 – 28
$289 CAD per night
4.9 out of 5 average rating, 61 reviews
Guest favourite
Cabin in Fredericktown
Harmony Hills Cabin on The Little St Francis River
Aug. 21 – 28
$206 CAD per night
4.97 out of 5 average rating, 64 reviews
Guest favourite
Cabin in Fredericktown
the evergreene
Jul. 25 – Aug. 1
$403 CAD per night
5.0 out of 5 average rating, 48 reviews
Guest favourite
Tiny homes in Fredericktown
Boho Retreat by Amidon Park
Dec. 6 – 13
$135 CAD per night
4.82 out of 5 average rating, 38 reviews

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