Annapolis Holiday Rentals from €114: Search Short-Term Rentals

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Holiday Rentals in Annapolis

Cozy cabin with a pitched roof, two windows, and a small porch.

"Enjoyed our stay in Annapolis! This cabin had everything we needed with plenty of space. Check in was super easy too! "

includes taxes & fees

3 Sept - 4 Sept

Cozy cabin-style building with a welcoming front porch and a pitched roof.

"Right by the black river. Cabin was amazing. It's very secluded. Our host was great! Nice and clean!"

Enjoy outdoor cooking and relaxation in this outdoor space with a grill and barbecue.

"Great time and a wonderful property"

Enjoy a warm gathering by the stone fireplace and grill, surrounded by comfortable seating under a covered pergola.

"We enjoyed the cabin at nights after floating the black river. "

"Five stars is easy when everything is perfect. Five stars is impressive when there's trouble. There were some technical problems when we arrived but the host was able to resolve the for us. We had a lovely stay. So, if you want gorgeous views and a lovely cottage and the assurance of a helpfuln host, then look no farther! "

includes taxes & fees

19 Aug - 20 Aug

Enjoy cooking and gathering in this cozy kitchen with a coffee maker, toaster, and knives.

"Plenty of privacy and everything you need. The owner was great at communicating."

includes taxes & fees

3 Sept - 4 Sept

Kitchen area with a stove, refrigerator, and coffee maker.

"Really a nice and clean and cozy stay."

includes taxes & fees

3 Sept - 4 Sept

Kitchen features a stove, microwave, and refrigerator, with a window and wooden cabinetry.

"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. "

includes taxes & fees

3 Sept - 4 Sept

Relax in this cozy space with a leather sofa, flat-screen TV, and dining area.

"Owner communicated well and the place was a nice clean place for us to stay "

includes taxes & fees

3 Sept - 4 Sept

Accessible cabin with a wooden deck and ramp entrance, set amidst a natural grassy area with a large tree.

"Nice, clean place to stay with excellent furnished kitchen!"

Relax outdoors in this serene patio area, complete with a pergola, table, and comfortable seating for dining or socializing.

"Love the people, town,float trip, and lil cabin#3 was perfect for family and pets"

includes taxes & fees

3 Sept - 4 Sept

Enjoy cooking in this well-equipped kitchen with a central island, sink, and stove, plus a convenient TV above the island.

"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."

includes taxes & fees

3 Sept - 4 Sept

Relax in a shaded outdoor space with seating options and a central table.

"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."

includes taxes & fees

3 Sept - 4 Sept

Relax on the covered patio with tables and chairs, adjacent to a building with a window and door.

"Beds were comfortable, outdoor area was wonderful, not far from town. Enjoyed our stay very much."

Enjoy a serene forest view from this deck, which offers a table and four comfortable rocking chairs.

"Good spot. Fun. Clean. Due for some minor repairs...couch, blinds, stove."

includes taxes & fees

3 Sept - 4 Sept

Kitchen area with flat-screen TV, central island, sink, coffee maker, and microwave.

"Cute little place, not far from the river"

includes taxes & fees

3 Sept - 4 Sept

Situated in a snowy forest, this cabin features a cozy front porch and a chimney.

includes taxes & fees

6 Sept - 7 Sept

Fully equipped kitchen with microwave, coffee maker, and stove, plus a convenient central island and sink.

"Beautiful property, I’d recommend to anyone going here to stay here."

includes taxes & fees

7 Sept - 8 Sept

Explore the serene riverbank with a nearby ATV.

"Great stay, very clean. Would definitely recommend to friends and stay again."

Enjoy cooking in this well-equipped kitchen with a gas stove, sink, and appliances.

includes taxes & fees

18 Aug - 19 Aug

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Top Annapolis Hotel Reviews

Secluded Log Cabin

10/10 Excellent

"Clean, cool, and comfortable. Recommend screenshoting the key code before arriving at the property.Maybe note how weak the wifi and cell service are in this location. "

Panther Den Cabin is located 4 miles from Hwy K Campground

10/10 Excellent

"It was seriously so cute! Nice & clean. Plenty of space & sleeping areas for our family of 6. Although, we didnt spend alot time actually in the cabin it was nice to come back to a nice cool place to relax for a bit and shower, after an entire evening in the rain (Friday) & full day of sun floating the black river (Saturday). I would highly recommend the Panthers Den to friends/family & if available next year we will be back!!! "

RIVER and SKY Cabin; Hot Tub

10/10 Excellent

"Five stars is easy when everything is perfect. Five stars is impressive when there's trouble. There were some technical problems when we arrived but the host was able to resolve the for us. We had a lovely stay. So, if you want gorgeous views and a lovely cottage and the assurance of a helpfuln host, then look no farther! "

Completely Renovated in May 2023

10/10 Excellent

"This cabin was excellent. We were not wanting to tent camp so this worked out great. You will need to bring a box fan or two as the A/C doesnt cool the bedrooms. The listing says washer/dryer but that is untrue (wasnt shocked though as it's a cabin). Our kids loved the train going by that was near for them. Blankets privided were great but bring your own pillows! We will definitely stay again. Our family wants to rent the one next to us too next time."

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 €114 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?

7 min to K Bridge Black River Annapolis MO Close to Clearwater Lake Piedmont : This highly rated holiday home rental in Annapolis is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. 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 Secluded Log Cabin.

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.

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Holiday Rentals in Annapolis

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Holiday Rentals in Annapolis

Hillside Cabin #4 Annapolis, MO Black River

Rustic River Cabin Getaway

Make your reservation fast as inquiries are coming in daily.

Relaxing 3B Log Home-15 min walk to the Black River!

RIVER and SKY Cabin; Hot Tub

Just Minutes from Black River – With WIFI

Hillside Cabin #3 Annapolis, MO Black River

FS Rental #1 - 5mins to Black River

New Cabin Just Minutes from Black River

Panther Den Cabin is located 4 miles from Hwy K Campground

Completely Renovated in May 2023

Hillside Cabin #5 Annapolis, MO

Hillside Cabin #1 Annapolis, MO Black River

Secluded Log Cabin

Hillside Cabin #2 Annapolis, MO Black River

Completely Renovated in May 2023

Sam A Baker State Park

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

Bluff View Inn and Resort

Johnson's Shut-ins State Park

Top Annapolis Hotel Reviews

Secluded Log Cabin

Shepherd Mountain Inn

Panther Den Cabin is located 4 miles from Hwy K Campground

Rustic River Cabin Getaway

RIVER and SKY Cabin; Hot Tub

FS Rental #1 - 5mins to Black River

Black River Motel and Restaurant

Completely Renovated in May 2023

Hillside Cabin #4 Annapolis, MO Black River

Find out more about Annapolis

Frequently asked questions