Annapolis Holiday Rentals

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Our top choices for Annapolis holiday rentals

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 AU$309
includes taxes & fees
21 Mar - 22 Mar
Hillside Cabin #2 Annapolis, MO Black River
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 AU$299
includes taxes & fees
10 Apr - 11 Apr
FS Rental #4 Annapolis, MO Black River
9.2 out of 10, Wonderful, (5 reviews)
"Great location and very clean."
United States
Mary C.
The price is AU$311
includes taxes & fees
22 Mar - 23 Mar
Hillside Cabin #5 Annapolis, MO
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 AU$359
includes taxes & fees
10 Apr - 11 Apr
Hillside Cabin #1 Annapolis, MO Black River

Cabin in Fredericktown

RIVER and SKY Cabin; Hot Tub
9.0 out of 10, Wonderful, (4 reviews)
"Great getaway"
United States
Anonymous traveller
The price is AU$354
includes taxes & fees
11 Mar - 12 Mar
RIVER and SKY Cabin; Hot Tub
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 AU$350
includes taxes & fees
20 Mar - 21 Mar
Small Town Lodge - Annapolis, MO Black River
7.2 out of 10, Good, (7 reviews)
"The home gave us a place to sleep and be out of the elements but the toilet was about to fall through the floor, wind was blowing through the windows, not enough bedding and the crazy neighbors stole our chair because they had broken theirs. Didn’t realize the train was right outside our bedroom and it blows the whistle every 2 hours. Again, we needed a place to stay and the home did the job. "
United States
Brandy H.
The price is AU$275
includes taxes & fees
10 Apr - 11 Apr
FS Rental #2 Annapolis, MO Black River
8.0 out of 10, Very good, (12 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.
FS Rental #3 Annapolis, MO Black River
9.8 out of 10, Exceptional, (9 reviews)
"Cute, cozy, clean, quiet. Outdoor shower was amazing."
United States
Zachary J.
The price is AU$184
includes taxes & fees
11 Mar - 12 Mar
Cozy Camper in the Woods w/ Trails & Fishing Pond - showcased by HGTV!
The price is AU$468
includes taxes & fees
16 Mar - 17 Mar
Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool

Mobile Home in Black

The Wyatt Earp
10.0 out of 10, Exceptional, (1 review)
"My family wanted to visit Johnson shut-in’s and I found this place to stay at it was perfect for us."
United States
Angela S.
The Wyatt Earp
8.8 out of 10, Excellent, (20 reviews)
"Loved this rental - great property!"
United States
Julie S.
The price is AU$305
includes taxes & fees
15 Mar - 16 Mar
St Francis River: The Blue Yurt and Hot Tub
10.0 out of 10, Exceptional, (2 reviews)
"Tina provides memorable touches and everything in the caboose is very well thought out, creating an enjoyable place to stay."
United States
Melissa
The price is AU$296
includes taxes & fees
12 Mar - 13 Mar
Unique Train Caboose with Loft & Firepit – Sleeps 4 – Fredericktown, MO

Cabin in Patterson

Sam A Baker State Park
2.0 star property
9.0 out of 10, Wonderful, (6 reviews)
"Pet friendly, great staff. "
United States
Charlie
The price is AU$202
includes taxes & fees
13 Mar - 14 Mar
Sam A Baker State Park
The price is AU$99
includes taxes & fees
11 Mar - 12 Mar
Wanderers End Sanctuary Forest Farm & Village Co-op
10.0 out of 10, Exceptional, (10 reviews)
"Amazing location. Very remote but if you like that then this is the location for you"
United States
Joshua P.
The price is AU$450
includes taxes & fees
11 Mar - 12 Mar
The Linkin: a cozy mountain cabin w/ king bed
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 AU$255
includes taxes & fees
11 Mar - 12 Mar
Lake Road Cabin C — Million Dollar Ozark View!
10.0 out of 10, Exceptional, (47 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 AU$294
includes taxes & fees
11 Mar - 12 Mar
The Sutton House 2 blocks from Main Street & Courthouse Square
10.0 out of 10, Exceptional, (34 reviews)
"enjoyed our stay, nice location to downtown and coffee. "
United States
Aaron L.
The price is AU$363
includes taxes & fees
11 Mar - 12 Mar
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch

Apartment in Ironton

Pickleball Cafe & Micro Hotel
10.0 out of 10, Exceptional, (21 reviews)
"Very nice place to stay! It was very well equipped. "
United States
Beth T.
The price is AU$331
includes taxes & fees
12 Mar - 13 Mar
Pickleball Cafe & Micro Hotel
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 favourite 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 depend 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 AU$255 per night. Entering your travel dates in the search wizard might find you 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?

The Sutton House 2 blocks from Main Street & Courthouse Square: This holiday home rental outside of Annapolis offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.