Holiday Rentals in Annapolis

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Holiday Rentals in Annapolis

Rustic River Cabin Getaway

Annapolis
9.8 out of 10, Exceptional, (79)
"This was our 2nd time staying at the cabin. Location is perfect! You can walk to the river and enjoy a swim, rope swing & exploring! Cabin is equipped with everything one needs, AC works great, clean & an amazing porch to sit and enjoy family! "
United States
John C.
Rustic River Cabin Getaway

Hillside Cabin #2 Annapolis, MO Black River

Annapolis
9.4 out of 10, Exceptional, (59)
"Good spot. Fun. Clean. Due for some minor repairs...couch, blinds, stove."
United States
Chris B.
The price is €196
includes taxes & fees
8 Nov - 9 Nov
Hillside Cabin #2 Annapolis, MO Black River

Make your reservation fast as inquiries are coming in daily.

Redford
9.8 out of 10, Exceptional, (55)
"Great time and a wonderful property"
United States
michael g.
Make your reservation fast as inquiries are coming in daily.

Completely Renovated in May 2023

Annapolis
9.6 out of 10, Exceptional, (5)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
The price is €188
includes taxes & fees
8 Nov - 9 Nov
Completely Renovated in May 2023

Hillside Cabin #3 Annapolis, MO Black River

Annapolis
7.8 out of 10, Good, (27)
"Good, pet friendly, all clean but carpet. Favorite place in Annapolis Mo"
United States
Chrystal B.
The price is €179
includes taxes & fees
10 Nov - 11 Nov
Hillside Cabin #3 Annapolis, MO Black River

Completely Renovated in May 2023

Annapolis
8.0 out of 10, Very good, (12)
"Love the people, town,float trip, and lil cabin#3 was perfect for family and pets"
United States
Jimmy S.
The price is €183
includes taxes & fees
8 Nov - 9 Nov
Completely Renovated in May 2023

Just Minutes from Black River – With WIFI

Annapolis
7.2 out of 10, Good, (7)
"Great experience "
United States
West n.
The price is €174
includes taxes & fees
8 Nov - 9 Nov
Just Minutes from Black River – With WIFI

Hillside Cabin #1 Annapolis, MO Black River

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 €227
includes taxes & fees
8 Nov - 9 Nov
Hillside Cabin #1 Annapolis, MO Black River

New Cabin Just Minutes from Black River

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 €226
includes taxes & fees
8 Nov - 9 Nov
New Cabin Just Minutes from Black River

Relaxing 3B Log Home-15 min walk to the Black River!

Annapolis
8.6 out of 10, Excellent, (11)
"We had a really good family time"
United States
Margarita M.
Relaxing 3B Log Home-15 min walk to the Black River!

Hillside Cabin #5 Annapolis, MO

Annapolis
9.2 out of 10, Wonderful, (5)
"Cabin was nice but the setting where the cabin was located kinda remote and not easy to find. Street leading to cabin was just a dirt road up a hill and looked like it lead to know where. "
United States
Elizabeth M.
The price is €196
includes taxes & fees
8 Nov - 9 Nov
Hillside Cabin #5 Annapolis, MO

RIVER and SKY Cabin; Hot Tub

Fredericktown
10.0 out of 10, Exceptional, (2)
"Great getaway"
United States
Anonymous traveller
The price is €219
includes taxes & fees
9 Nov - 10 Nov
RIVER and SKY Cabin; Hot Tub

Panther Den Cabin is located 4 miles from Hwy K Campground

Annapolis.
9.6 out of 10, Exceptional, (14)
"It was seriously so cute! Nice & clean. Plenty of space & sleeping areas for our family of 6. Although, we didnt spend alot time actually in the cabin it was nice to come back to a nice cool place to relax for a bit and shower, after an entire evening in the rain (Friday) & full day of sun floating the black river (Saturday). I would highly recommend the Panthers Den to friends/family & if available next year we will be back!!! "
United States
josh R.
Panther Den Cabin is located 4 miles from Hwy K Campground

Micro house cabin located near Silver Mines Recreation Area.

Fredericktown
10.0 out of 10, Exceptional, (75)
"We had a wonderful stay with Shirley, definitely would be back again!"
United States
sofia n.
Micro house cabin located near Silver Mines Recreation Area.

Charming 2 bedroom cabin on a beautiful private lake.

Ironton
9.4 out of 10, Exceptional, (16)
"Place is nice & easy to find. "
United States
Mercy
The price is €174
includes taxes & fees
9 Nov - 10 Nov
Charming 2 bedroom cabin on a beautiful private lake.

L-Wood Acres: Peaceful Cabin in Arcadia Valley

Ironton
9.8 out of 10, Exceptional, (48)
"This was the perfect location for our first trip as a family of 4! The house was perfect and close to so many things to do."
United States
Erin S.
L-Wood Acres: Peaceful Cabin in Arcadia Valley

Sam A Baker State Park

2.0 star property
Patterson
9.2 out of 10, Wonderful, (5)
"Pet friendly, great staff. "
United States
Charlie
The price is €115
includes taxes & fees
8 Nov - 9 Nov
Sam A Baker State Park

The Sutton House 2 blocks from Main Street & Courthouse Square

Ironton
10.0 out of 10, Exceptional, (41)
"Perfect location for all the nearby state parks. Bedrooms are generous sized areas so individuals could have some down-time in their own area if they wished. We loved it and would stay again. "
United States
Angela H.
The price is €125
includes taxes & fees
4 Dec - 5 Dec
The Sutton House 2 blocks from Main Street & Courthouse Square

16 Acres of beauty and relaxation

Park Hills
9.8 out of 10, Exceptional, (18)
"Quiet place in the woods exactly what I wanted!"
United States
Jeremy R.
16 Acres of beauty and relaxation

Lake Road Cabin B — Million Dollar Ozark View!

Ironton
10.0 out of 10, Exceptional, (23)
"Beautiful place."
United States
Brian K.
Lake Road Cabin B — Million Dollar Ozark View!
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, apart-hotels, 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 €115 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?

Secluded Log Cabin: This highly rated holiday home rental in Annapolis is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind. Some other top choices in Annapolis are Just Minutes from Black River – With WIFI and 7 min to K Bridge Black River Annapolis MO Close to Clearwater Lake Piedmont .

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.