Annapolis Holiday Rentals

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Our top choices for Annapolis holiday rentals

Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (59)
"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$377
includes taxes & fees
30 Dec - 31 Dec
Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #5 Annapolis, MO

Hillside Cabin #5 Annapolis, MO
Annapolis
9.2 out of 10, Wonderful, (5)
"Great location and very clean."
United States
Mary C.
The price is NZ$377
includes taxes & fees
30 Dec - 31 Dec
Hillside Cabin #5 Annapolis, MO

FS Rental #4 Annapolis, MO Black River

FS Rental #4 Annapolis, MO Black River
Annapolis
9.6 out of 10, Exceptional, (7)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
The price is NZ$361
includes taxes & fees
1 Jan - 2 Jan 2026
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)
"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
30 Dec - 31 Dec
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)
"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
30 Dec - 31 Dec
Hillside Cabin #1 Annapolis, MO Black River

RIVER and SKY Cabin; Hot Tub

RIVER and SKY Cabin; Hot Tub
Fredericktown
10.0 out of 10, Exceptional, (2)
"Great getaway"
United States
Anonymous traveller
The price is NZ$423
includes taxes & fees
4 Jan - 5 Jan 2026
RIVER and SKY Cabin; Hot Tub

FS Rental #3 Annapolis, MO Black River

FS Rental #3 Annapolis, MO Black River
Annapolis
8.0 out of 10, Very good, (12)
"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$352
includes taxes & fees
30 Dec - 31 Dec
FS Rental #3 Annapolis, MO Black River

5 camper hookups on a beautiful private lake.

5 camper hookups on a beautiful private lake.
1.0 star property
Ironton
10.0 out of 10, Exceptional, (1)
"Great place to enjoy camping"
United States
ChangHee S.
The price is NZ$55
includes taxes & fees
30 Dec - 31 Dec
5 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
30 Dec - 31 Dec
Wanderers End Sanctuary Forest Farm & Village Co-op

The Wyatt Earp

The Wyatt Earp
Black
10.0 out of 10, Exceptional, (1)
"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 price is NZ$478
includes taxes & fees
30 Dec - 31 Dec
The Wyatt Earp

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, (18)
"Loved this rental - great property!"
United States
Julie S.
The price is NZ$354
includes taxes & fees
30 Dec - 31 Dec
St Francis River: The Blue Yurt and Hot Tub

Cozy train caboose with cupola loft and firepit-Sleeps 4

Cozy train caboose with cupola loft and firepit-Sleeps 4
2.0 star property
Fredericktown
The price is NZ$348
includes taxes & fees
30 Dec - 31 Dec
Cozy train caboose with cupola loft and firepit-Sleeps 4

Sam A Baker State Park

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 NZ$227
includes taxes & fees
31 Dec - 1 Jan 2026
Sam A Baker State Park

Lake Road Cabin C — Million Dollar Ozark View!

Lake Road Cabin C — Million Dollar Ozark View!
Ironton
10.0 out of 10, Exceptional, (24)
"Girls weekend enjoyed our time. Just a great little cabin so we could enjoy the parks!"
United States
Jeanine H.
The price is NZ$271
includes taxes & fees
30 Dec - 31 Dec
Lake Road Cabin C — Million Dollar Ozark View!

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, (10)
"Amazing location. Very remote but if you like that then this is the location for you"
United States
Joshua P.
The price is NZ$504
includes taxes & fees
30 Dec - 31 Dec
The Linkin: a cozy mountain cabin w/ king bed

Mountain View at Pickle & Perk

Mountain View at Pickle & Perk
2.5 star property
Ironton
10.0 out of 10, Exceptional, (19)
"Very cute place in beautiful area. Easy check-in, clean home, and comfy bed. The coffee shop below was really good with a beautiful patio. Location was perfect to access Elephant Rocks, Johnson Shut-ins, and Taum Sauk Mountain parks. "
United States
Amber S.
The price is NZ$328
includes taxes & fees
1 Jan - 2 Jan 2026
Mountain View at Pickle & Perk

Pickleball Cafe & Micro Hotel

Pickleball Cafe & Micro Hotel
Ironton
10.0 out of 10, Exceptional, (19)
"The perfect combination of quaint and modern! Loved the decor and getting to enjoy dinner on the porch outside overlooking the patio. Would definitely stay again!"
United States
Alexandra Z.
The price is NZ$356
includes taxes & fees
5 Jan - 6 Jan 2026
Pickleball Cafe & Micro Hotel

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

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
Ironton
10.0 out of 10, Exceptional, (33)
"Very friendly, helpful host, clean and cute house. Love the area for shops, and hiking we had a wonderful stay!"
United States
beth s.
The price is NZ$426
includes taxes & fees
30 Dec - 31 Dec
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch

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, (45)
"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 NZ$275
includes taxes & fees
11 Jan - 12 Jan 2026
The Sutton House 2 blocks from Main Street & Courthouse Square

AV Bungalows #9B

AV Bungalows #9B
Arcadia
10.0 out of 10, Exceptional, (2)
"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$286
includes taxes & fees
30 Dec - 31 Dec
AV Bungalows #9B
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$227 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?

Mark Twain National Forest and K Bridge Recreation Area 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.