Search Annapolis Cottages

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
In two months
In three months
In four months
No exact matches found, but these alternatives could be just right

Recommended hotels in Annapolis

9.4 out of 10, Exceptional, (59)
"great place to get away. plan to cook/grill there, or drive 30 minutes for food. however, this solitude and quiet is exactly why we booked here. and gorgeous roads, hikes, sites in every direction."
United States
Hans S.
$220 nightly
The price is $220
Dec 23 - Dec 24
Total with taxes and fees
Hillside Cabin #2 Annapolis, MO Black River
9.2 out of 10, Wonderful, (5)
"Great location and very clean."
United States
Mary C.
$220 nightly
The price is $220
Dec 23 - Dec 24
Total with taxes and fees
Hillside Cabin #5 Annapolis, MO
9.4 out of 10, Exceptional, (36)
"The cabin was exactly like the pictures showed. It worked out perfectly for our family with just enough room to spread out, and with a large main area that we could hang out together comfortably. We took advantage of the spacious patio and enjoyed a fire each night. I would definitely stay again."
United States
Amy A.
$255 nightly
The price is $255
Dec 23 - Dec 24
Total with taxes and fees
Hillside Cabin #1 Annapolis, MO Black River
9.6 out of 10, Exceptional, (7)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
$211 nightly
The price is $211
Dec 23 - Dec 24
Total with taxes and fees
FS Rental #4 Annapolis, MO Black River
9.0 out of 10, Wonderful, (7)
"Owner communicated well and the place was a nice clean place for us to stay "
United States
Jeremy H.
$254 nightly
The price is $254
Dec 23 - Dec 24
Total with taxes and fees
Small Town Lodge - Annapolis, MO Black River

Cabin in Fredericktown

RIVER and SKY Cabin; Hot Tub
10.0 out of 10, Exceptional, (2)
"Great getaway"
United States
Anonymous traveler
$236 nightly
The price is $247
Jan 4 - Jan 5, 2026
Total with taxes and fees
RIVER and SKY Cabin; Hot Tub
7.8 out of 10, Good, (27)
"Really a nice and clean and cozy stay."
United States
Adam G.
$201 nightly
The price is $201
Dec 23 - Dec 24
Total with taxes and fees
Hillside Cabin #3 Annapolis, MO Black River
8.0 out of 10, Very Good, (12)
"Enjoyed our stay. Our 2nd time staying here for our canoe trip. Patio area is nice for relaxing outside also. Canoe rental place Jeff's canoe only about 8 min away. And Iron Mule and Thee Abby Kitchen nice place to eat. "
United States
Denise R.
$205 nightly
The price is $205
Dec 24 - Dec 25
Total with taxes and fees
FS Rental #3 Annapolis, MO Black River

Fort Davidson Hotel

Fort Davidson Hotel
2.5 star property
9.2 out of 10, Wonderful, (174)
"Friendly staff, spacious room, nice pool!!"
United States
SHARON
$120 nightly
The price is $131
Dec 23 - Dec 24
Total with taxes and fees
Fort Davidson Hotel

Motel in Fredericktown

Madison Inn Lodge
2.5 star property
7.6 out of 10, Good, (297)
"Room was not exactly smelling nice, but room was clean and comfortable. The lodge was close to expressway and shopping. Staff was very friendly. I would stay there again."
United States
Steve
$78 nightly
The price is $85
Jan 1 - Jan 2, 2026
Total with taxes and fees
Madison Inn Lodge
1.0 star property
10.0 out of 10, Exceptional, (1)
"Great place to enjoy camping"
United States
ChangHee S.
$32 nightly
The price is $32
Dec 23 - Dec 24
Total with taxes and fees
5 camper hookups on a beautiful private lake.
8.8 out of 10, Excellent, (18)
"Loved this rental - great property!"
United States
Julie S.
$198 nightly
The price is $207
Dec 23 - Dec 24
Total with taxes and fees
St Francis River: The Blue Yurt and Hot Tub

Cabin in Patterson

Sam A Baker State Park
2.0 star property
9.2 out of 10, Wonderful, (5)
"Pet friendly, great staff. "
United States
Charlie
$125 nightly
The price is $132
Dec 23 - Dec 24
Total with taxes and fees
Sam A Baker State Park

Bed & Breakfast in Arcadia

Arcadia Academy
3.0 star property
9.8 out of 10, Exceptional, (11)
"Love the charm of the room with the hard wood floors, architecture, friendly staff and great food"
United States
Joann
$136 nightly
The price is $148
Dec 23 - Dec 24
Total with taxes and fees
Arcadia Academy

Shepherd Mountain Inn

Shepherd Mountain Inn
2.5 star property
9.4 out of 10, Exceptional, (304)
" Nice room, nice bed, convenient location"
United States
Burton
$120 nightly
The price is $131
Dec 23 - Dec 24
Total with taxes and fees
Shepherd Mountain Inn
$65 nightly
The price is $69
Dec 23 - Dec 24
Total with taxes and fees
Wanderers End Sanctuary Forest Farm & Village Co-op
10.0 out of 10, Exceptional, (24)
"Girls weekend enjoyed our time. Just a great little cabin so we could enjoy the parks!"
United States
Jeanine H.
$149 nightly
The price is $158
Dec 23 - Dec 24
Total with taxes and fees
Lake Road Cabin C — Million Dollar Ozark View!
2.0 star property
$203 nightly
The price is $203
Dec 25 - Dec 26
Total with taxes and fees
Cozy train caboose with cupola loft and firepit-Sleeps 4
10.0 out of 10, Exceptional, (45)
"Adorable house with everyone you need provided! Super clean and the beds were very comfy. Will stay here again on our next trip to the area. "
United States
Brandi
$142 nightly
The price is $160
Jan 11 - Jan 12, 2026
Total with taxes and fees
The Sutton House 2 blocks from Main Street & Courthouse Square
10.0 out of 10, Exceptional, (10)
"Amazing location. Very remote but if you like that then this is the location for you"
United States
Joshua P.
$279 nightly
The price is $294
Dec 30 - Dec 31
Total with taxes and fees
The Linkin: a cozy mountain cabin w/ king bed
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Annapolis Hotel Reviews

Find out more about Annapolis

Annapolis Cottages information

Number of reviews
1,003
Accommodation
13 Cottages
Lowest Price
$32
Highest Price
$294

Frequently asked questions

Why book your cottage in Annapolis with Expedia?
Expedia has some wonderful cottages in Annapolis, so get ready for an unforgettable stay on nature's doorstep. If you have a set budget, click on how much you'd like to spend and your preferred property star rating. Or, make the most of our filters to search for cottages with a pool or a hot tub. We'll help you find the perfect place whatever your plans or style of travel.
How can I find cheap cottages in Annapolis?
The quickest way to locate cheap cottages in Annapolis is with Expedia's filter tool. Narrow down your search by amenities, star rating and budget to access awesome bargains in a few clicks.
What is there to do in Annapolis near my cottage?
Once you've unpacked your bags, venture out and discover the amazing things Annapolis has on offer. Walnut Hollow Lake is a great attraction to add to your itinerary.

Explore a world of travel with Expedia