Annapolis Holiday Rentals

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Our top choices for Annapolis holiday rentals

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 NZ$376
includes taxes & fees
1 Apr - 2 Apr
Hillside Cabin #5 Annapolis, MO

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 NZ$376
includes taxes & fees
1 Apr - 2 Apr
Hillside Cabin #2 Annapolis, MO Black River

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 NZ$362
includes taxes & fees
1 Apr - 2 Apr
FS Rental #4 Annapolis, MO Black River

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 NZ$435
includes taxes & fees
1 Apr - 2 Apr
Small Town Lodge - Annapolis, MO Black River

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 NZ$437
includes taxes & fees
5 Apr - 6 Apr
Hillside Cabin #1 Annapolis, MO Black River

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 NZ$331
includes taxes & fees
11 Apr - 12 Apr
FS Rental #2 Annapolis, MO Black River

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 NZ$433
includes taxes & fees
2 Apr - 3 Apr
RIVER and SKY Cabin; Hot Tub

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 NZ$362
includes taxes & fees
1 Apr - 2 Apr
FS Rental #3 Annapolis, MO Black River

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, (9 reviews)
"Cute, cozy, clean, quiet. Outdoor shower was amazing."
United States
Zachary J.
The price is NZ$224
includes taxes & fees
2 Apr - 3 Apr
Cozy Camper in the Woods w/ Trails & Fishing Pond - showcased by HGTV!

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 NZ$60
includes taxes & fees
1 Apr - 2 Apr
5 electric camper hookups on a beautiful private lake.

Wanderers End Sanctuary Forest Farm & Village Co-op

Wanderers End Sanctuary Forest Farm & Village Co-op
Clubb
The price is NZ$118
includes taxes & fees
1 Apr - 2 Apr
Wanderers End Sanctuary Forest Farm & Village Co-op

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, (21 reviews)
"Loved this rental - great property!"
United States
Julie S.
The price is NZ$371
includes taxes & fees
1 Apr - 2 Apr
St Francis River: The Blue Yurt and Hot Tub

Sleep in a Real Train Caboose Unique Missouri Getaway

Sleep in a Real Train Caboose Unique Missouri Getaway
Fredericktown
10.0 out of 10, Exceptional, (2 reviews)
"The place was clean, smelled fresh, the muffins she had were amazing. Every little detail about the place being a train cargo was perfect. The hooks for towls and toilet paper being part of the rail road. The flashing lights when coming into the property was very neat. The fire pit was perfect and she supplied the wood, lighter, and fire starter. Everything about this place was amzing. Will definitely be back. Worth the 4 hour drive."
United States
Sarah L.
The price is NZ$360
includes taxes & fees
1 Apr - 2 Apr
Sleep in a Real Train Caboose Unique Missouri Getaway

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 NZ$249
includes taxes & fees
2 Apr - 3 Apr
Sam A Baker State Park

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 NZ$363
includes taxes & fees
1 Apr - 2 Apr
Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool

Lake Road Cabin C — Million Dollar Ozark View!

Lake Road Cabin C — Million Dollar Ozark View!
Ironton
10.0 out of 10, Exceptional, (24 reviews)
"Yes the cabin and area were awesome, we will come back "
United States
J D.
The price is NZ$311
includes taxes & fees
2 Apr - 3 Apr
Lake Road Cabin C — Million Dollar Ozark View!

Charming 2 bedroom cabin on a beautiful private lake.

Charming 2 bedroom cabin on a beautiful private lake.
Ironton
9.4 out of 10, Exceptional, (21 reviews)
"Place is nice & easy to find. "
United States
Mercy
The price is NZ$481
includes taxes & fees
8 Apr - 9 Apr
Charming 2 bedroom cabin on a beautiful private lake.

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

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
Ironton
10.0 out of 10, Exceptional, (35 reviews)
"enjoyed our stay, nice location to downtown and coffee. "
United States
Aaron L.
The price is NZ$458
includes taxes & fees
1 Apr - 2 Apr
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch

AV Bungalows #9B

AV Bungalows #9B
Arcadia
10.0 out of 10, Exceptional, (2 reviews)
"My husband and I really enjoyed our stay! The Bungalow was perfect for us and will definitely be staying again when we come back to Arcadia!!"
United States
Theresa R.
The price is NZ$290
includes taxes & fees
1 Apr - 2 Apr
AV Bungalows #9B

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 NZ$360
includes taxes & fees
1 Apr - 2 Apr
Mountain View 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.
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Top Annapolis Hotel Reviews

Find out more about Annapolis

Everything you need to know about Annapolis holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Annapolis holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Annapolis holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annapolis. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Annapolis holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Annapolis holiday rentals we have selected for you start as low as NZ$331 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Annapolis rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Annapolis holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Annapolis. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.