Annapolis Holiday Rentals from €183: Search Short-Term Rentals

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Holiday Rentals in Annapolis

"This is a cozy little home in a small town within a nine minute drive of Turkey Run State park, and nine miles from Shades State Park and Rockville ( which has some quaint specialty and antique stores). The host has it well stocked (above and beyond what most VRBO hosts do) with snacks, condiments, and a coffe bar! Stacie was very responsive to all my texts and questions throughout our stay. It suited my sister and I well for our stay."

"My Sister in law and I went with daughter in laws. We had a great time. We ate too much, decorated cakes and did Christmas card decorating. It was a very special weekend."

"Very clean and comfortable. Property owner communicated well, we will be back."

"We really enjoyed out stay. Place is immaculate and comfortable. Loved the covered outside deck and so did our Scottie dog! Wish we could have stayed longer. Will definitely look forward to staying there again. Thank you Bob and Joanne!"

includes taxes & fees

2 Dec - 3 Dec

"It was very nice, and cozy, and enjoyed the stay!! Would for sure recommend!"

"Lots of space to gather. Great location. We had a great weekend!"

includes taxes & fees

9 Dec - 10 Dec

"We celebrated a birthday in this beautiful place! The hideaway cabin was the perfect size for us and it felt incredibly homey and cozy. The hot tub was perfect and we had an absolute blast. Couldn’t have had a better birthday weekend so close to home! The hosts were incredibly kind and informative and we had privacy and were completely relaxed the entire weekend! Highly recommend this property "

includes taxes & fees

1 Dec - 2 Dec

"Thank you for the beautiful stay!! "

"We had a great stay. Nice quiet location , all the amenities you would need in a stay no matter what time of year. Tony and Lisa were great hosts . .W W"

"Brian was great at quickly responding to questions. House just as advertised. Very clean. Hot tub and fire pit with wood available but we didn’t use. (May want to add night stand lamps in bedrooms and reading light in living room, as there is mostly just ceiling lights) very close to Bridgeton, primary location of Covered Bridge Festival. "

includes taxes & fees

29 Dec - 30 Dec

"Better than a 5 star hotel!"

"We spent most of our time hiking, but this cabin was very nice. It would definitely be good for a family with all the outdoor space, games, etc. Check in and communication were great, and the location to Shades State park can’t be beat. We will definitely stay again if back in this area."

"This property is a real gem and I commend the owners for recognizing the potential and for saving a piece of the community’s history! The quirky-ness makes this a really fun getaway and makes you feel like a kid again! Me and my sister (both 50+) took advantage of the facility each evening of our stay. We played HORSE on the basketball court, played ping pong and air hockey and watched several of the movies provided. It was also just cool to explore the school although a little spooky at times...

3 bedrooms, travel cot, free WiFi, bed sheets

"The Cabin was Picturesque; clean, comfortable, and quiet. The Host was amazing, kind, and always quick to respond to any questions we had. "

3 bedrooms, iron/ironing board, free WiFi, bed sheets

"Very. Clean very welcoming was very helpful letting us in early to prepare fir wedding. After wedding returning to house felt like comming home. Thank you."

includes taxes & fees

12 Dec - 13 Dec

"What a lovey place. Kevin is a wonderful host. It was SO clean, which is my #1 priority always, so I was happy with it. The bed was super comfortable. The surroundings are beautiful. "

includes taxes & fees

3 Dec - 4 Dec

"Great location - 1 block off main town square where all activities were happening. Property is a bit dated, but was very clean and tidy."

"We were so excited to find a 3 bedroom/3 bath near Turkey Run State Park for 3 couples to meet for a fall getaway. This "Barn" home is exceptional. The wide open living area provided space for everyone to enjoy from watching TV, reading a book, or playing a game of pool. We loved hiking and having dinner at the State Park and were excited to find Coxford Covered Bridge, just down the Road from this home. The owners were very easy to work with and the property exceeded our expectations."

"There was no Cable, or WIFI as stated in the listing. There was not running water as stated in the listing. The heating/AC unit was very poor and did not keep the house warm. There was dog hair all over the place, yet the listing stated pet free. There were leaks on the walls with brown streaks running down the walls that had not been tended to. The linens smelled as if they had not been washed. There were dead bugs all over the walls and windows in the bathroom. The bathroom and bedroom windows...

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Other types of properties in Annapolis you may be interested in

"Saw the 2024 eclipse there. Room was spacious and clean. Shower had hot water with good pressure."

"This is a cozy little home in a small town within a nine minute drive of Turkey Run State park, and nine miles from Shades State Park and Rockville ( which has some quaint specialty and antique stores). The host has it well stocked (above and beyond what most VRBO hosts do) with snacks, condiments, and a coffe bar! Stacie was very responsive to all my texts and questions throughout our stay. It suited my sister and I well for our stay."

"My Sister in law and I went with daughter in laws. We had a great time. We ate too much, decorated cakes and did Christmas card decorating. It was a very special weekend."

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 €183 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.

Recent reviews of Annapolis properties

The Getaway House with Hot Tub and Pool. Pet Friendly

5/5 Excellent

Hunting retreat

"We had a great stay. Nice quiet location , all the amenities you would need in a stay no matter what time of year. Tony and Lisa were great hosts . .W W"

A verified traveller stayed at The Getaway House with Hot Tub and Pool. Pet Friendly

Posted 2 days ago

Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly

5/5 Excellent

An entire elementary school to yourself!!

"This property is a real gem and I commend the owners for recognizing the potential and for saving a piece of the community’s history! The quirky-ness makes this a really fun getaway and makes you feel like a kid again! Me and my sister (both 50+) took advantage of the facility each evening of our stay. We played HORSE on the basketball court, played ping pong and air hockey and watched several of the movies provided. It was also just cool to explore the school although a little spooky at times but even that made it very memorable. This is a great location. Close to Turkey Run, which is a beautiful park and in a good location to explore the local covered bridges and the awesome assortment of antique stores. We stayed 3 nights and had plenty to do and see on our visit and could have used a few more days because we ran out of time to see Shades park. The apartment was clean and comfortable and was all that we needed for a great home base. Would definitely stay here again if in the area. Thanks to the owners for a unique and memorable experience!"

A verified traveller from Henryville, IN stayed at Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly

Posted 7 days ago

Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

5/5 Excellent

Great little house

"Very clean and comfortable. Property owner communicated well, we will be back."

A verified traveller from Clarkston MI stayed at Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

Posted 10 days ago

Quaint century-old home just minutes from Turkey Run & Shades State Park

5/5 Excellent

Great little house

"This is a cozy little home in a small town within a nine minute drive of Turkey Run State park, and nine miles from Shades State Park and Rockville ( which has some quaint specialty and antique stores). The host has it well stocked (above and beyond what most VRBO hosts do) with snacks, condiments, and a coffe bar! Stacie was very responsive to all my texts and questions throughout our stay. It suited my sister and I well for our stay."

A verified traveller from Fort Wayne IN stayed at Quaint century-old home just minutes from Turkey Run & Shades State Park

Posted 3 weeks ago

Getaway in the country/Beautiful Parke County/Large hot tub and much more!

5/5 Excellent

Great stay in beautiful Indiana country

"We celebrated a birthday in this beautiful place! The hideaway cabin was the perfect size for us and it felt incredibly homey and cozy. The hot tub was perfect and we had an absolute blast. Couldn’t have had a better birthday weekend so close to home! The hosts were incredibly kind and informative and we had privacy and were completely relaxed the entire weekend! Highly recommend this property "

A verified traveller from Munster, USA stayed at Getaway in the country/Beautiful Parke County/Large hot tub and much more!

Posted 3 weeks ago

A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.

5/5 Excellent

Loved it!!!!

"We really enjoyed out stay. Place is immaculate and comfortable. Loved the covered outside deck and so did our Scottie dog! Wish we could have stayed longer. Will definitely look forward to staying there again. Thank you Bob and Joanne!"

A verified traveller from Longmont, CO stayed at A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.

Posted 3 weeks ago

Frequently asked questions

Can I find holiday rentals 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.

What are some of the best holiday rentals that Annapolis has to offer?

Quaint century-old home just minutes from Turkey Run & Shades State Park : This holiday home rental outside of Annapolis is located in a rural location, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Annapolis?

While you're exploring the area, Turkey Run State Park and Shades State Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Billie Creek Village and Bridgeton Covered Bridge.

What’s a holiday rental in Annapolis like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Annapolis. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

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Holiday Rentals in Annapolis

Check Annapolis holiday rental availability

Holiday Rentals in Annapolis

Quaint century-old home just minutes from Turkey Run & Shades State Park

Charming lake cabin located next to Racoon State Park.

Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.

Millstone Hideaway

Nestled near woods and creek, this large home is near state parks and colleges..

Getaway in the country/Beautiful Parke County/Large hot tub and much more!

This home is located in beautiful Parke County, a rustic and charming setting.

The Getaway House with Hot Tub and Pool. Pet Friendly

The Rosedale House

Sugar Creek Escape at Turkey Run

Remodeled Log Cabin Surrounded By 6000 Acres and includes a Nordic Spa!

Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly

Treetops Cabin in the Woods!

1960's Ranch House NO CLEANING FEE

Secluded in The Woods

The Dragonfly Guest House, 3 Bedroom, 3 Bath, sleeps 8

Luxury Amish Built Barn Home at Turkey Run

Greencastle Tiny House, Walk to Raccoon Lake!

Other types of properties in Annapolis you may be interested in

Royal Inn Rockville

Quaint century-old home just minutes from Turkey Run & Shades State Park

Charming lake cabin located next to Racoon State Park.

Find out more about Annapolis

Recent reviews of Annapolis properties

The Getaway House with Hot Tub and Pool. Pet Friendly

Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly

Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

Sugar Creek Escape at Turkey Run

Quaint century-old home just minutes from Turkey Run & Shades State Park

Getaway in the country/Beautiful Parke County/Large hot tub and much more!

Millstone Hideaway

A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.

Treetops Cabin in the Woods!

Frequently asked questions