Annapolis Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Annapolis vacation rentals

A compact kitchen with wooden cabinets, a large TV, and various kitchen utensils hanging on the wall.

1. FS Rental #4 Annapolis, MO Black River

FS Rental #4 Annapolis, MO Black River
Annapolis
9.2 out of 10, Wonderful, (11 reviews)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
$193 nightly
The price is $193
Nov 10 - Nov 11
Total with taxes and fees
FS Rental #4 Annapolis, MO Black River
A cabin interior with a loft bed, a chair, and a ceiling fan.

2. Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (66 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.
$201 nightly
The price is $201
Nov 10 - Nov 11
Total with taxes and fees
Hillside Cabin #2 Annapolis, MO Black River
A kitchen with dark cabinets, a stainless steel refrigerator, a built-in oven, a microwave, and a flat-screen TV mounted above the counter.

3. 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.
$201 nightly
The price is $201
Nov 10 - Nov 11
Total with taxes and fees
Hillside Cabin #5 Annapolis, MO
A cozy living room with a brown leather sofa, a small table with a lamp, and a wooden floor. A kitchen with wooden cabinets and a dining area with a table and chairs are visible in the background.

4. Small Town Lodge - Annapolis, MO Black River

Small Town Lodge - Annapolis, MO Black River
Annapolis
8.4 out of 10, Very good, (10 reviews)
"Owner communicated well and the place was a nice clean place for us to stay "
United States
Jeremy H.
$233 nightly
The price is $233
Nov 10 - Nov 11
Total with taxes and fees
Small Town Lodge - Annapolis, MO Black River
A kitchen with wooden cabinets, a central island with stools, a microwave, a refrigerator, and a stove.

5. Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River
Annapolis
9.6 out of 10, Exceptional, (41 reviews)
"The cabin was perfect for our needs! It was clean and perfect size and convenient to the Black River and town to get supplies."
United States
Rik B.
$234 nightly
The price is $234
Nov 10 - Nov 11
Total with taxes and fees
Hillside Cabin #1 Annapolis, MO Black River
Living Room & Dining Area

6. FS Rental #1 Annapolis, MO Black River

FS Rental #1 Annapolis, MO Black River
Annapolis
8.0 out of 10, Very good, (7 reviews)
"we had a great stay"
United States
Jasonl C.
$216 nightly
The price is $216
Nov 10 - Nov 11
Total with taxes and fees
FS Rental #1 Annapolis, MO Black River
A modern kitchen with a large TV, stainless steel appliances, and a wooden floor.

7. FS Rental #3 Annapolis, MO Black River

FS Rental #3 Annapolis, MO Black River
Annapolis
8.4 out of 10, Very good, (15 reviews)
"Ac needs an update, or add window units. Beautiful stay and beautiful location. About 7 minutes from the river. Train runs in front at 1am and 4am just a heads up. "
United States
Jessica W.
$189 nightly
The price is $189
Nov 15 - Nov 16
Total with taxes and fees
FS Rental #3 Annapolis, MO Black River
A wooden deck with chairs and a fire pit in a forested area.

8. Hillside Cabin #3 Annapolis, MO Black River

Hillside Cabin #3 Annapolis, MO Black River
Annapolis
7.8 out of 10, Good, (30 reviews)
"Really a nice and clean and cozy stay."
United States
Adam G.
$185 nightly
The price is $185
Nov 10 - Nov 11
Total with taxes and fees
Hillside Cabin #3 Annapolis, MO Black River
A modern room with a large window, two chairs, a small wooden table, and a view of a forest.

9. RIVER and SKY Cabin; Hot Tub

RIVER and SKY Cabin; Hot Tub
Fredericktown
9.2 out of 10, Wonderful, (7 reviews)
"Lpleasant environment, beautiful view, the cabin was super clean and enjoyableonly note being the bed was stiff and pillows were thin but overall would recommend"
United States
Teresa C.
$219 nightly
The price is $233
Nov 10 - Nov 11
Total with taxes and fees
RIVER and SKY Cabin; Hot Tub
A kitchen with wooden cabinets, a microwave, a coffee maker, a stove, and a sink.

10. Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
Piedmont
10.0 out of 10, Exceptional, (48 reviews)
"Would stay here again"
United States
Steve A.
$125 nightly
The price is $132
Nov 10 - Nov 11
Total with taxes and fees
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
A wooden deck structure with a red exterior and string lights, a car parked nearby, and a tree in the foreground.

11. Cozy hobby farm cabin under the stars with treehouse, & hot tub

Cozy hobby farm cabin under the stars with treehouse, & hot tub
Patterson
9.6 out of 10, Exceptional, (12 reviews)
"Easy check in, very quiet, very calming and relaxing. Overall great stay and great property manager. "
United States
Wyatt S.
$103 nightly
The price is $109
Nov 23 - Nov 24
Total with taxes and fees
Cozy hobby farm cabin under the stars with treehouse, & hot tub
A modern living room with a fireplace, leather sofa, and a flat-screen TV mounted above it.

12. Arcadia Valley Bungalows #3 with Hot Tub/Outdoor Pool

Arcadia Valley Bungalows #3 with Hot Tub/Outdoor Pool
Arcadia
10.0 out of 10, Exceptional, (1 review)
"Cute bungalow; perfect for me and my husband while in Arcadia to visit family."
United States
Julie H.
$176 nightly
The price is $190
Nov 10 - Nov 11
Total with taxes and fees
Arcadia Valley Bungalows #3 with Hot Tub/Outdoor Pool
A rustic log cabin with a stone foundation, surrounded by trees and a wooden fence.

13. 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
$150 nightly
The price is $159
Nov 10 - Nov 11
Total with taxes and fees
Sam A Baker State Park
A rustic wooden cabin with a porch, a swing, and a welcome sign.

14. Escape to Clearwater Lake and Upper Black River, Pet Friendly

Escape to Clearwater Lake and Upper Black River, Pet Friendly
Piedmont
10.0 out of 10, Exceptional, (3 reviews)
"Clean rooms. Great quality of craftsmanship in the cabin. Cold ac full fridge. Everything looked exactly like the pics ..you get what you pay for and more. Will definitely go back again. And recommend"
United States
Mike A.
$169 nightly
The price is $178
Nov 10 - Nov 11
Total with taxes and fees
Escape to Clearwater Lake and Upper Black River, Pet Friendly
A kitchen with wooden cabinets, a black refrigerator, a stainless steel sink, and a wall clock.

15. Lake Road Cabin C — Million Dollar Ozark View!

Lake Road Cabin C — Million Dollar Ozark View!
Ironton
10.0 out of 10, Exceptional, (34 reviews)
"Great cabin. Very quiet area. Nice fire pit."
United States
Heather the Librarian
$156 nightly
The price is $167
Nov 10 - Nov 11
Total with taxes and fees
Lake Road Cabin C — Million Dollar Ozark View!
A modern kitchen with dark cabinets, a built-in microwave, a flat-screen TV, and a large window with a view of the street.

16. Ironton Hub: Near Elephant Rocks & Shut-Ins

Ironton Hub: Near Elephant Rocks & Shut-Ins
Ironton
10.0 out of 10, Exceptional, (3 reviews)
"Great stay. Perfect for the short stay we needed. Clean and convenient. Will recommend."
United States
angie m.
$173 nightly
The price is $188
Nov 10 - Nov 11
Total with taxes and fees
Ironton Hub: Near Elephant Rocks & Shut-Ins
A modern kitchen with dark cabinets, a built-in microwave, a flat-screen TV, and a large window with a view of the street.

17. Ironton Hub: Near Elephant Rocks & Shut-ins

Ironton Hub: Near Elephant Rocks & Shut-ins
3.0 star property
Ironton
$182 nightly
The price is $198
Nov 10 - Nov 11
Total with taxes and fees
Ironton Hub: Near Elephant Rocks & Shut-ins
Interior

18. Hidden Hollow Cabin. Charming 2-bedroom cabin on a beautiful lake.

Hidden Hollow Cabin. Charming 2-bedroom cabin on a beautiful lake.
Ironton
9.8 out of 10, Exceptional, (36 reviews)
"This cabin was sooo cozy, and the location was excellent! So quiet and peaceful!Great place to enjoy God's country!"
United States
shirley w.
$290 nightly
The price is $310
Nov 29 - Nov 30
Total with taxes and fees
Hidden Hollow Cabin. Charming 2-bedroom cabin on a beautiful lake.
A compact living space with a sofa, a flat-screen TV mounted on the wall, a red refrigerator, and wooden beams on the ceiling.

19. The Mustard Seed - Cozy Tiny Home in the Ozarks

The Mustard Seed - Cozy Tiny Home in the Ozarks
Patterson
$110 nightly
The price is $116
Nov 10 - Nov 11
Total with taxes and fees
The Mustard Seed - Cozy Tiny Home in the Ozarks
A dining area with a table and chairs, wooden cabinets, and a kitchen with an archway.

20. Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.

Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
Lesterville
9.0 out of 10, Wonderful, (20 reviews)
"Ellen is a Very communicative and helpful host. Property looks even better in person than in the pictures. Enjoyable stay!"
United States
Robert H.
$445 nightly
The price is $469
Nov 10 - Nov 11
Total with taxes and fees
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
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

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, a stove, and a granite countertop.
Shepherd Mountain Inn

Shepherd Mountain Inn

Shepherd Mountain Inn
Ironton

10/10 Excellent

We lived in Arcadia Valley 20 years ago. We revisited to show our grandson where his dad grew up. We were pleasantly surprised when we booked your motel. The renovations were nicely done. Your manager was very friendly and picked the perfect room for us as we returned daily from hiking and visiting old friends. The daily breakfast exceeded our expectations especially the warm food. Every area was clean and well kept by management and cleaning team. We recommend this motel to others when they...
United States
Gwen
Reviewed June 10, 2023
Shepherd Mountain Inn

Find out more about Annapolis

Everything you need to know about Annapolis vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annapolis vacation 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 low season months. For more hustle and bustle, you may prefer to visit Annapolis in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis vacation 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 vacation.

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 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?

Secluded Log Cabin: Visitors give good reviews to this Annapolis vacation home rental, which is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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.

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