Annapolis Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Annapolis holiday rentals

2 bedrooms, iron/ironing board, free WiFi, bed sheets

Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (59 reviews)
"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 HK$948
HK$1,660 total
includes taxes & fees
22 Apr - 23 Apr
Hillside Cabin #2 Annapolis, MO Black River
Fridge, microwave, oven, stovetop

Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (36 reviews)
"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 HK$1,034
HK$1,935 total
includes taxes & fees
22 Apr - 23 Apr
Hillside Cabin #1 Annapolis, MO Black River
Fridge, microwave, oven, stovetop

FS Rental #4 Annapolis, MO Black River

FS Rental #4 Annapolis, MO Black River
Annapolis
9.6 out of 10, Exceptional, (7 reviews)
"This was a great place to stay, so close to my job site. Comfortable, clean and well furnished. I would definitely stay here again!"
United States
Steven G.
The price is HK$862
HK$1,653 total
includes taxes & fees
23 Apr - 24 Apr
FS Rental #4 Annapolis, MO Black River
Smart TV

Small Town Lodge - Annapolis, MO Black River

Small Town Lodge - Annapolis, MO Black River
Annapolis
9.0 out of 10, Wonderful, (7 reviews)
"Owner communicated well and the place was a nice clean place for us to stay "
United States
Jeremy H.
The price is HK$1,034
HK$1,927 total
includes taxes & fees
22 Apr - 23 Apr
Small Town Lodge - Annapolis, MO Black River
Exterior

Secluded Log Cabin

Secluded Log Cabin
Annapolis
9.8 out of 10, Exceptional, (26 reviews)
"Stay was fine, nice peaceful setting, enjoyed our stay and would come back or recommend to others, thank you"
United States
Glen J.
The price is HK$901
HK$1,658 total
includes taxes & fees
3 May - 4 May
Secluded Log Cabin
Fridge, microwave, oven, stovetop

Hillside Cabin #5 Annapolis, MO

Hillside Cabin #5 Annapolis, MO
Annapolis
9.2 out of 10, Wonderful, (5 reviews)
"Great location and very clean."
United States
Mary C.
The price is HK$948
HK$1,660 total
includes taxes & fees
21 Apr - 22 Apr
Hillside Cabin #5 Annapolis, MO
Interior

RIVER and SKY Cabin; Hot Tub

RIVER and SKY Cabin; Hot Tub
Fredericktown
9.0 out of 10, Wonderful, (4 reviews)
"Great getaway"
United States
Anonymous traveller
The price is HK$1,245
HK$1,958 total
includes taxes & fees
26 Apr - 27 Apr
RIVER and SKY Cabin; Hot Tub
Smart TV

FS Rental #1 Annapolis, MO Black River

FS Rental #1 Annapolis, MO Black River
Annapolis
7.6 out of 10, Good, (5 reviews)
"We enjoyed our stay here. It was a great place for the 8 of us to stay. We were going over to Sam A Baker to join family camping there. We would stay here again if available. "
United States
Sue F.
The price is HK$1,163
HK$2,064 total
includes taxes & fees
4 May - 5 May
FS Rental #1 Annapolis, MO Black River
Fridge, microwave, oven, stovetop

FS Rental #3 Annapolis, MO Black River

FS Rental #3 Annapolis, MO Black River
Annapolis
8.2 out of 10, Very good, (13 reviews)
"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.
The price is HK$862
HK$1,606 total
includes taxes & fees
22 Apr - 23 Apr
FS Rental #3 Annapolis, MO Black River
Fridge, microwave, oven, coffee/tea maker

FS Rental #2 Annapolis, MO Black River

FS Rental #2 Annapolis, MO Black River
Annapolis
7.2 out of 10, Good, (7 reviews)
"Great experience "
United States
West n.
The price is HK$775
HK$1,519 total
includes taxes & fees
23 Apr - 24 Apr
FS Rental #2 Annapolis, MO Black River
Outdoor pool

Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool

Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool
Fredericktown
The price is HK$1,371
HK$1,627 total
includes taxes & fees
21 Apr - 22 Apr
Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool
Interior

Cozy Camper in the Woods w/ Trails & Fishing Pond - showcased by HGTV!

Cozy Camper in the Woods w/ Trails & Fishing Pond - showcased by HGTV!
Farmington
9.8 out of 10, Exceptional, (10 reviews)
"Cute, cozy, clean, quiet. Outdoor shower was amazing."
United States
Zachary J.
The price is HK$564
HK$1,006 total
includes taxes & fees
21 Apr - 22 Apr
Cozy Camper in the Woods w/ Trails & Fishing Pond - showcased by HGTV!
Property grounds

5 electric camper hookups on a beautiful private lake.

5 electric camper hookups on a beautiful private lake.
Ironton
10.0 out of 10, Exceptional, (1 review)
"Great place to enjoy camping"
United States
ChangHee S.
The price is HK$106
HK$270 total
includes taxes & fees
21 Apr - 22 Apr
5 electric camper hookups on a beautiful private lake.
Living area

St Francis River: The Blue Yurt and Hot Tub

St Francis River: The Blue Yurt and Hot Tub
Fredericktown
8.8 out of 10, Excellent, (22 reviews)
"Everything was easy to understand to find the place I wanted. Host is 5 stars"
United States
Ronnah B.
The price is HK$980
HK$1,655 total
includes taxes & fees
21 Apr - 22 Apr
St Francis River: The Blue Yurt and Hot Tub
Property grounds

Wanderers End Sanctuary Forest Farm & Village Co-op

Wanderers End Sanctuary Forest Farm & Village Co-op
Clubb
The price is HK$352
HK$530 total
includes taxes & fees
21 Apr - 22 Apr
Wanderers End Sanctuary Forest Farm & Village Co-op
Room

Sam A Baker State Park

Sam A Baker State Park
2.0 star property
Patterson
9.0 out of 10, Wonderful, (6 reviews)
"Pet friendly, great staff. "
United States
Charlie
The price is HK$1,057
HK$1,120 total
includes taxes & fees
21 Apr - 22 Apr
Sam A Baker State Park
Exterior

The Linkin: a cozy mountain cabin w/ king bed

The Linkin: a cozy mountain cabin w/ king bed
Ironton
10.0 out of 10, Exceptional, (11 reviews)
"Amazing location. Very remote but if you like that then this is the location for you"
United States
Joshua P.
The price is HK$1,449
HK$2,507 total
includes taxes & fees
23 Apr - 24 Apr
The Linkin: a cozy mountain cabin w/ king bed
Outdoor dining

The King Suite at Pickle & Perk

The King Suite at Pickle & Perk
Ironton
10.0 out of 10, Exceptional, (2 reviews)
"Very nice and clean room. The building itself was really cute! The manager was really nice, coffee was really good too! Looking forward to staying again! "
United States
Timothy A.
The price is HK$1,050
HK$1,492 total
includes taxes & fees
21 Apr - 22 Apr
The King Suite at Pickle & Perk
Exterior

AV Bungalows #8

AV Bungalows #8
Arcadia
The price is HK$1,225
HK$1,486 total
includes taxes & fees
21 Apr - 22 Apr
AV Bungalows #8
Terrace/patio

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
Ironton
10.0 out of 10, Exceptional, (36 reviews)
"enjoyed our stay, nice location to downtown and coffee. "
United States
Aaron L.
The price is HK$1,077
HK$2,046 total
includes taxes & fees
21 Apr - 22 Apr
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
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.
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Top Annapolis Hotel Reviews

Johnson's Shut-ins State Park

Johnson's Shut-ins State Park

10/10 Excellent
"The cabin was beautiful with everything you could ever need! My one note would be the handicap shower pressure was abysmal but everything else was great "
Dacota 2-night trip
Posted 7 days ago
Johnson's Shut-ins State Park

Find out more about Annapolis

Search for holiday rentals in Annapolis on Expedia! You can easily find your home rentals, villas, holiday apartments in Annapolis using one of the methods below:

  • View our selection of featured holiday rentals in Annapolis
  • Use the map to find apartments and other holiday homes in the Annapolis neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Annapolis while they last

Look no further and take a look at our great range of rental properties in Annapolis!

Frequently asked questions

Can I find a holiday rental in Annapolis?

Yes, there are holiday rentals close to the most popular sights in Annapolis, or you can select a more secluded option if you're looking for a relaxing stay. Annapolis is known for its riverfront and parks. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that Annapolis has to offer?

FS Rental #2 Annapolis, MO Black River: This highly rated holiday home rental in Annapolis is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, an oven and a microwave.

How many holiday rentals are there in Annapolis?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Annapolis stay.

What can I see and do in Annapolis?

K Bridge Recreation Area and Mark Twain National Forest are a couple of lovely local spots to get outside and enjoy nature. While here, Taum Sauk Mountain State Park and Walnut Hollow Lake are other places worth a visit.

What are holiday rentals like in Annapolis?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Annapolis. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.