Search Cottages in Annapolis

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Cottages in Annapolis

No exact matches found, but these alternatives could be just right

Recommended hotels in Annapolis

Cabin in Annapolis

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.
The price is SAR 495
SAR 957 total
includes taxes & fees
1 Dec - 2 Dec
Hillside Cabin #1 Annapolis, MO Black River

Cabin 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.
The price is SAR 454
SAR 822 total
includes taxes & fees
1 Dec - 2 Dec
Hillside Cabin #2 Annapolis, MO Black River

Cabin in Annapolis

9.2 out of 10, Wonderful, (5)
"Great location and very clean."
United States
Mary C.
The price is SAR 454
SAR 822 total
includes taxes & fees
1 Dec - 2 Dec
Hillside Cabin #5 Annapolis, MO

Cabin in Annapolis

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.
The price is SAR 409
SAR 787 total
includes taxes & fees
1 Dec - 2 Dec
Completely Renovated in May 2023

Cabin in Annapolis

8.0 out of 10, Very Good, (12)
"Loved the space!!! Ran out of toilet paper but luckily had extra paper towels! Ceiling fan had an annoying drumming noise. Great location, close to eats…liquor locker has great burgers!!!"
United States
Adam W.
The price is SAR 392
SAR 767 total
includes taxes & fees
1 Dec - 2 Dec
Completely Renovated in May 2023

Cabin in Annapolis

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.
The price is SAR 495
SAR 953 total
includes taxes & fees
1 Dec - 2 Dec
New Cabin Just Minutes from Black River

Cabin in Annapolis

7.8 out of 10, Good, (27)
"Really a nice and clean and cozy stay."
United States
Adam G.
The price is SAR 392
SAR 752 total
includes taxes & fees
1 Dec - 2 Dec
Hillside Cabin #3 Annapolis, MO Black River

Cabin in Fredericktown

10.0 out of 10, Exceptional, (2)
"Great getaway"
United States
Anonymous traveler
The price is SAR 844
SAR 1,220 total
includes taxes & fees
31 Dec - 1 January 2026
RIVER and SKY Cabin; Hot Tub

Fort Davidson Hotel

2.5 star property
9.2 out of 10, Wonderful, (172)
"Friendly staff, spacious room, nice pool!!"
United States
SHARON
The price is SAR 450
SAR 492 total
includes taxes & fees
1 Dec - 2 Dec
Fort Davidson Hotel

Motel in Fredericktown

2.5 star property
7.6 out of 10, Good, (296)
"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
The price is SAR 292
SAR 319 total
includes taxes & fees
1 Dec - 2 Dec
Madison Inn Lodge

Bed & Breakfast in Arcadia

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
The price is SAR 485
SAR 526 total
includes taxes & fees
1 Dec - 2 Dec
Arcadia Academy

Shepherd Mountain Inn

2.5 star property
9.4 out of 10, Exceptional, (304)
" Nice room, nice bed, convenient location"
United States
Burton
Shepherd Mountain Inn

Cabin in Fredericktown

8.8 out of 10, Excellent, (18)
"Loved it would stay again "
United States
Ashley B.
The price is SAR 521
SAR 836 total
includes taxes & fees
30 Dec - 31 Dec
St Francis River: The Blue Yurt and Hot Tub

Cabin in Patterson

2.0 star property
9.2 out of 10, Wonderful, (5)
"Pet friendly, great staff. "
United States
Charlie
The price is SAR 469
SAR 497 total
includes taxes & fees
2 Dec - 3 Dec
Sam A Baker State Park

Camping in Clubb

The price is SAR 169
SAR 259 total
includes taxes & fees
1 Dec - 2 Dec
Wanderers End Sanctuary Forest Farm & Village Co-op

Camping in Ironton

1.0 star property
The price is SAR 45
SAR 120 total
includes taxes & fees
1 Dec - 2 Dec
5 camper hookups on a beautiful private lake.

Cabin in Ironton

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.
The price is SAR 405
SAR 670 total
includes taxes & fees
1 Dec - 2 Dec
Lake Road Cabin C — Million Dollar Ozark View!

Cabin in Piedmont

10.0 out of 10, Exceptional, (33)
"Beautiful property, I’d recommend to anyone going here to stay here."
United States
tom
The price is SAR 431
SAR 506 total
includes taxes & fees
2 Dec - 3 Dec
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

Cabin in Ironton

9.4 out of 10, Exceptional, (16)
"Place is nice & easy to find. "
United States
Mercy
The price is SAR 490
SAR 733 total
includes taxes & fees
1 Dec - 2 Dec
Charming 2 bedroom cabin on a beautiful private lake.

Aparthotel in Ironton

10.0 out of 10, Exceptional, (2)
"Jrrat people and just beautifully decorated. "
United States
Tamara S.
The price is SAR 503
SAR 672 total
includes taxes & fees
1 Dec - 2 Dec
The King Suite at Pickle & Perk
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.

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Save an average of 15% on thousands of hotels when you're signed in

Top Annapolis Hotel Reviews

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.