Default HTG hotel image

Holiday Rentals in Annapolis

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Annapolis holiday rentals

1. Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River
Annapolis
9.2 out of 10, Wonderful, (61 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 €189
includes taxes & fees
11 Sept - 12 Sept
Hillside Cabin #2 Annapolis, MO Black River

2. FS Rental #4 Annapolis, MO Black River

FS Rental #4 Annapolis, MO Black River
Annapolis
9.6 out of 10, Exceptional, (7 reviews)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
The price is €196
includes taxes & fees
10 Sept - 11 Sept
FS Rental #4 Annapolis, MO Black River

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.
Hillside Cabin #5 Annapolis, MO

4. Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (40 reviews)
"Very grateful for this safe clean cabin. We were there during the terrible Black River flooding and thankfully this cabin was in safe high ground. "
United States
Leslie
The price is €255
includes taxes & fees
10 Sept - 11 Sept
Hillside Cabin #1 Annapolis, MO Black River

5. Small Town Lodge - Annapolis, MO Black River

Small Town Lodge - Annapolis, MO Black River
Annapolis
9.0 out of 10, Wonderful, (8 reviews)
"Owner communicated well and the place was a nice clean place for us to stay "
United States
Jeremy H.
The price is €214
includes taxes & fees
11 Sept - 12 Sept
Small Town Lodge - Annapolis, MO Black River

6. FS Rental #1 Annapolis, MO Black River

FS Rental #1 Annapolis, MO Black River
Annapolis
7.6 out of 10, Good, (5 reviews)
"We enjoyed our stay here. It was a great place for the 8 of us to stay. We were going over to Sam A Baker to join family camping there. We would stay here again if available. "
United States
Sue F.
The price is €229
includes taxes & fees
12 Aug - 13 Aug
FS Rental #1 Annapolis, MO Black River

7. FS Rental #3 Annapolis, MO Black River

FS Rental #3 Annapolis, MO Black River
Annapolis
8.2 out of 10, Very good, (13 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.
The price is €177
includes taxes & fees
11 Sept - 12 Sept
FS Rental #3 Annapolis, MO Black River

8. Hillside Cabin #3 Annapolis, MO Black River

Hillside Cabin #3 Annapolis, MO Black River
Annapolis
7.8 out of 10, Good, (27 reviews)
"Really a nice and clean and cozy stay."
United States
Adam G.
The price is €179
includes taxes & fees
11 Sept - 12 Sept
Hillside Cabin #3 Annapolis, MO Black River

9. RIVER and SKY Cabin; Hot Tub

RIVER and SKY Cabin; Hot Tub
Fredericktown
9.4 out of 10, Exceptional, (6 reviews)
"Great getaway"
United States
Anonymous traveller
The price is €220
includes taxes & fees
16 Aug - 17 Aug
RIVER and SKY Cabin; Hot Tub

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, (43 reviews)
"Perfect cabin for a fishing trip. My Dad and I loved staying there."
United States
Anonymous traveller
The price is €131
includes taxes & fees
12 Aug - 13 Aug
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

11. 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 €124
includes taxes & fees
18 Aug - 19 Aug
Sam A Baker State Park

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

Lake Road Cabin C — Million Dollar Ozark View!
Ironton
10.0 out of 10, Exceptional, (30 reviews)
"This is a very cozy, comfortable and quiet space. This cabin has everything you need and is close to restaurants and Elephant Rocks State Park. I would recommend to anyone visiting the area! Thank you!"
United States
Michelle
The price is €159
includes taxes & fees
12 Aug - 13 Aug
Lake Road Cabin C — Million Dollar Ozark View!

13. Cozy hobby farm cabin under the stars!

Cozy hobby farm cabin under the stars!
Greenville
10.0 out of 10, Exceptional, (8 reviews)
"Easy check in, very quiet, very calming and relaxing. Overall great stay and great property manager. "
United States
Wyatt S.
The price is €107
includes taxes & fees
9 Sept - 10 Sept
Cozy hobby farm cabin under the stars!

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

Ironton Hub: Near Elephant Rocks & Shut-ins
3.0 star property
Ironton
The price is €189
includes taxes & fees
12 Aug - 13 Aug
Ironton Hub: Near Elephant Rocks & Shut-ins

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

Ironton Hub: Near Elephant Rocks & Shut-Ins
Ironton
10.0 out of 10, Exceptional, (1 review)
"Great stay. Perfect for the short stay we needed. Clean and convenient. Will recommend."
United States
angie m.
The price is €191
includes taxes & fees
20 Aug - 21 Aug
Ironton Hub: Near Elephant Rocks & Shut-Ins

16. 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 €148
includes taxes & fees
24 Aug - 25 Aug
AV Bungalows #9B

17. 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, (19 reviews)
"Great house and location."
United States
Thomas M.
The price is €432
includes taxes & fees
12 Aug - 13 Aug
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.

18. Mountain View at Pickle & Perk

Mountain View at Pickle & Perk
Ironton
10.0 out of 10, Exceptional, (28 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 €180
includes taxes & fees
12 Aug - 13 Aug
Mountain View at Pickle & Perk

19. 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
9.8 out of 10, Exceptional, (8 reviews)
"This was one of the best stays we have ever had! The owners Cathy and Richard are absolutely incredible! They go above and beyond to make sure you have the best time possible! The amities are just non stop! I 100% recommend and will definitely be back!"
United States
Lexis
The price is €183
includes taxes & fees
12 Aug - 13 Aug
Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool

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

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
Ironton
10.0 out of 10, Exceptional, (39 reviews)
"Great place to stay!"
United States
Derek R.
The price is €249
includes taxes & fees
25 Aug - 26 Aug
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
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.
Save an average of 15% on thousands of hotels when you're signed in

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 €107 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.

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.