Annapolis Holiday Rentals

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Holiday Rentals in Annapolis

Rustic River Cabin Getaway
9.8 out of 10, Exceptional, (79)
"This was our second stay here and we are trying to make it an annual trip. Cabin is awesome along with location on the river, you can’t beat it. "
United States
Sam E.
Rustic River Cabin Getaway
Hillside Cabin #2 Annapolis, MO Black River
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 AU$337
includes taxes & fees
27 Oct - 28 Oct
Hillside Cabin #2 Annapolis, MO Black River
New Cabin Just Minutes from Black River
8.4 out of 10, Very good, (5)
"Owner communicated well and the place was a nice clean place for us to stay "
United States
Jeremy H.
The price is AU$391
includes taxes & fees
18 Nov - 19 Nov
New Cabin Just Minutes from Black River
Make your reservation fast as inquiries are coming in daily.
9.8 out of 10, Exceptional, (55)
"We loved the view from overlook cabin. Cabin was clean and cozy. Follow directions property manager sends you because gps will try to take you on a scavenger hunt but this was my fault. Accessing river a sxs or 4x4 definitely needed due to river being up. Very peaceful setting at river and cabin."
United States
Greg V.
Make your reservation fast as inquiries are coming in daily.
FS Rental #1 - 5mins to Black River
7.6 out of 10, Good, (5)
"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.
FS Rental #1 - 5mins to Black River
Completely Renovated in May 2023
9.6 out of 10, Exceptional, (5)
"Cute little place, not far from the river"
United States
Alissa K.
The price is AU$323
includes taxes & fees
27 Oct - 28 Oct
Completely Renovated in May 2023
Completely Renovated in May 2023
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 AU$317
includes taxes & fees
19 Nov - 20 Nov
Completely Renovated in May 2023
Hillside Cabin #3 Annapolis, MO Black River
7.8 out of 10, Good, (27)
"Really a nice and clean and cozy stay."
United States
Adam G.
The price is AU$309
includes taxes & fees
27 Oct - 28 Oct
Hillside Cabin #3 Annapolis, MO Black River
Secluded Log Cabin
9.6 out of 10, Exceptional, (25)
"If you want to be secluded this is the place for you. You are away from it all. Amazing secluded cabin that is close to multiple great state parks! "
United States
Don H.
Secluded Log Cabin
Just Minutes from Black River – With WIFI
7.2 out of 10, Good, (7)
"Great experience "
United States
West n.
The price is AU$299
includes taxes & fees
18 Nov - 19 Nov
Just Minutes from Black River – With WIFI
Hillside Cabin #1 Annapolis, MO Black River
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 AU$393
includes taxes & fees
18 Nov - 19 Nov
Hillside Cabin #1 Annapolis, MO Black River
RIVER and SKY Cabin; Hot Tub
10.0 out of 10, Exceptional, (2)
"Great getaway"
United States
Anonymous traveller
The price is AU$386
includes taxes & fees
27 Oct - 28 Oct
RIVER and SKY Cabin; Hot Tub
Hillside Cabin #5 Annapolis, MO
9.2 out of 10, Wonderful, (5)
"Booked a last minute canoe trip on the Black River andn this property was ideally located and included everything necessary for an early breakfast before hitting the river."
United States
Courtney C.
The price is AU$337
includes taxes & fees
18 Nov - 19 Nov
Hillside Cabin #5 Annapolis, MO
Relaxing 3B Log Home-15 min walk to the Black River!
8.6 out of 10, Excellent, (11)
"We enjoyed the cabin at nights after floating the black river. "
United States
Brian K.
Relaxing 3B Log Home-15 min walk to the Black River!
Panther Den Cabin is located 4 miles from Hwy K Campground
9.6 out of 10, Exceptional, (14)
"Nice, clean place to stay with excellent furnished kitchen!"
United States
Sandy M.
Panther Den Cabin is located 4 miles from Hwy K Campground
The Sutton House 2 blocks from Main Street & Courthouse Square
10.0 out of 10, Exceptional, (40)
"We had a wonderful stay and looking forward to returning again!"
United States
Renee R.
The price is AU$251
includes taxes & fees
3 Nov - 4 Nov
The Sutton House 2 blocks from Main Street & Courthouse Square
Sam A Baker State Park
2.0 star property
9.2 out of 10, Wonderful, (5)
"Pet friendly, great staff. "
United States
Charlie
The price is AU$203
includes taxes & fees
27 Oct - 28 Oct
Sam A Baker State Park
Micro house cabin located near Silver Mines Recreation Area.
10.0 out of 10, Exceptional, (73)
"This was my second visit and am planning to return again someday. Very quiet and cozy. "
United States
eric y.
Micro house cabin located near Silver Mines Recreation Area.
Charming 2 bedroom cabin on a beautiful private lake.
9.4 out of 10, Exceptional, (13)
"Place is nice & easy to find. "
United States
Mercy
The price is AU$304
includes taxes & fees
29 Oct - 30 Oct
Charming 2 bedroom cabin on a beautiful private lake.
L-Wood Acres: Peaceful Cabin in Arcadia Valley
9.8 out of 10, Exceptional, (46)
"Quiet location, comfortable indoors and great deck for relaxing."
United States
Jan P.
L-Wood Acres: Peaceful Cabin in Arcadia Valley
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$203 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?

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.