Annapolis Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Annapolis vacation 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 ￥20,679
￥35,875 total
includes taxes & fees
May 10 - May 11
Hillside Cabin #2 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 ￥19,817
￥35,640 total
includes taxes & fees
May 10 - May 11
FS Rental #4 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 ￥18,056
￥32,760 total
includes taxes & fees
May 13 - May 14
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 ￥20,679
￥35,875 total
includes taxes & fees
May 7 - May 8
Hillside Cabin #5 Annapolis, MO
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 ￥27,572
￥47,624 total
includes taxes & fees
May 4 - May 5
Small Town Lodge - Annapolis, MO Black River
Fridge, microwave, oven, stovetop

Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River
Annapolis
9.6 out of 10, Exceptional, (37 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 ￥25,849
￥45,901 total
includes taxes & fees
May 4 - May 5
Hillside Cabin #1 Annapolis, MO Black River
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 ￥23,264
￥41,280 total
includes taxes & fees
May 4 - May 5
FS Rental #1 Annapolis, MO Black River
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 traveler
The price is ￥24,909
￥39,488 total
includes taxes & fees
May 13 - May 14
RIVER and SKY Cabin; Hot Tub
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 ￥19,862
￥35,720 total
includes taxes & fees
May 3 - May 4
FS Rental #3 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
10.0 out of 10, Exceptional, (1 review)
"This place is exactly as advertised. Very modern/updated decor and facilities. The place was immaculately clean and the host provided many nice extras (bottled waters, snacks, etc). The hot tub was very nice! The house is situated on the host's property, about 100 yds from their home. Meaning they were available if needed, but left us to our privacy. Definitely would rent again!"
United States
Jeff S.
The price is ￥27,416
￥33,176 total
includes taxes & fees
May 6 - May 7
Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool
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 ￥2,115
￥5,402 total
includes taxes & fees
May 4 - May 5
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 ￥19,598
￥33,566 total
includes taxes & fees
May 5 - May 6
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 ￥7,050
￥10,605 total
includes taxes & fees
May 7 - May 8
Wanderers End Sanctuary Forest Farm & Village Co-op
Family Cabin

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 ￥21,149
￥22,412 total
includes taxes & fees
May 7 - May 8
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 ￥28,982
￥50,142 total
includes taxes & fees
May 6 - May 7
The Linkin: a cozy mountain cabin w/ king bed
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)
"Great place to stay!"
United States
Derek R.
The price is ￥22,107
￥42,047 total
includes taxes & fees
May 17 - May 18
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
1 bedroom, in-room safe, desk, iron/ironing board

Mountain View at Pickle & Perk

Mountain View at Pickle & Perk
Ironton
10.0 out of 10, Exceptional, (20 reviews)
"Our stay was excellent. The rooms were cozy and a perfect location to get to Elephant Rock and Johnson Shut-Ins."
United States
Cara J.
The price is ￥22,418
￥32,053 total
includes taxes & fees
May 6 - May 7
Mountain View at Pickle & Perk
Outdoor dining

Pickleball Cafe & Micro Hotel

Pickleball Cafe & Micro Hotel
Ironton
10.0 out of 10, Exceptional, (23 reviews)
"Very nice place to stay! It was very well equipped. "
United States
Beth T.
The price is ￥26,648
￥36,131 total
includes taxes & fees
May 6 - May 7
Pickleball Cafe & Micro Hotel
Smart TV, books

Arcadia Valley Bungalows #5 with seasonal outdoor pool and year-round swim spa

Arcadia Valley Bungalows #5 with seasonal outdoor pool and year-round swim spa
Arcadia
The price is ￥24,509
￥31,504 total
includes taxes & fees
May 4 - May 5
Arcadia Valley Bungalows #5 with seasonal outdoor pool and year-round swim spa
Interior

The Sutton House 2 blocks from Main Street & Courthouse Square

The Sutton House 2 blocks from Main Street & Courthouse Square
Ironton
10.0 out of 10, Exceptional, (56 reviews)
"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
The price is ￥26,692
￥32,451 total
includes taxes & fees
May 4 - May 5
The Sutton House 2 blocks from Main Street & Courthouse Square
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
"Nice property"
Aleksandr 2-night trip
Posted 2 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:

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

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Frequently asked questions

Can I find a vacation rental in Annapolis?

Yes, we give you a choice of vacation rentals close to top local attractions in Annapolis, or you can select a more secluded option if you want a relaxing place to 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 vacation rentals in Annapolis?

FS Rental #2 Annapolis, MO Black River: Visitors give good reviews to this Annapolis vacation home rental, which is equipped with a barbecue grill, 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 vacation rentals are there in Annapolis?

With 3 Expedia vacation rentals, you're sure 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 vacation rentals like in Annapolis?

Vacation rentals are private accommodations you can stay in for a short or long stay in Annapolis. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.