Chewsville Holiday Rentals

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Holiday Rentals in Chewsville

Cozy Quiet Cabin Near Historic Gettysburg / Liberty Mountain Resort

10.0 out of 10, Exceptional, (1)
"The secluded and pristine property was an absolute joy to come back to after a long day on the mountain. The constant sound of the babbling creek just steps away from the back deck created the perfect setting for a wonderful mountain getaway. Also, our dog loved roaming the land and seeing the occasional Deer grazing in the woods. I highly recommend booking here. If we ever come back to ski at Liberty resort, this will be the first place I look for to stay in!"
Cozy Quiet Cabin Near Historic Gettysburg / Liberty Mountain Resort

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (53)
"The cabin was perfect for a few days of writing and reflecting! Everything was very clean and it was easy communicating with the owner. The house is not "secluded" as there are neighboring houses on two sides and if I hadn't brought an ax/saw to cut my own dry wood enjoying a fire wouldn't have been possible. But overall a lovely stay and I look forward to going again!"
The price is AU$176
includes taxes & fees
3 Mar - 4 Mar
❤️ Secluded 1940s Romantic Tiny House on the River

Cozy streamside cabin, convenient to Ski Liberty and Gettysburg

9.4 out of 10, Exceptional, (209)
"Such a beautiful home on the stream! We loved every bit of it especially the gorgeous views. Paul was great, very responsive, and let us check in a few hours early. No issues with anything!"
Cozy streamside cabin, convenient to Ski Liberty and Gettysburg

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (90)
"Absolutely beautiful cozy and idyllic and Cassandra was extremely responsive! Also very close to amazing hiking at Gambrills park. Ill be back! "
Countryside Cabin with Mountain Views near Surreybrooke Gardens

The SKI SLOPES are open and we are only minutes away. Book your stay now!!!

10.0 out of 10, Exceptional, (20)
"Great cabin. Close to slopes. Enjoyed it. "
The price is AU$210
includes taxes & fees
21 Feb - 22 Feb
The SKI SLOPES are open and we are only minutes away. Book your stay now!!!

Charming "Cream of the Crop" Cape ~❤️of Middletown

10.0 out of 10, Exceptional, (119)
"But the warmth of the home helped our stay."
The price is AU$447
includes taxes & fees
24 Feb - 25 Feb
Charming "Cream of the Crop" Cape ~❤️of Middletown

Beautiful, Spacious Historic Victorian Near Ski Liberty

9.8 out of 10, Exceptional, (53)
"This was the 2nd year our group of families stayed at this home, and it was more perfect than last year. We arrived Friday last afternoon and evening, and everything was as described. Saturday, a quick 10 minute drive and we were at the slopes for a ski day at Liberty Resort. The proximity is perfect, so in the evening, we drove the teems back for more skiing while the adults hung out at the house. Sunday was a beautiful and perfect snow day. We had planned on a chill games day at the house, and...
Beautiful, Spacious Historic Victorian Near Ski Liberty

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

10.0 out of 10, Exceptional, (25)
"What a great home. The host obviously took the extra steps to make sure guests are comfortable and well cared for. Very cozy!"
The price is AU$442
includes taxes & fees
23 Feb - 24 Feb
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

Walk to Liberty Mountain: Lake-View Ski Retreat!

10.0 out of 10, Exceptional, (2)
"The house was very close to Liberty Mountain where the family spent most of the day skiing/snowboarding. The house was very clean and the host was very easy to contact and checked in with us to see how our stay was going. The stairs were a little tight, but nothing that we couldn't manage."
Walk to Liberty Mountain: Lake-View Ski Retreat!

Misty Mountain Lodge Pickleball Liberty Ski

10.0 out of 10, Exceptional, (16)
"Great location, we lucked out and had a snow-filled weekend. Perfect secluded spot to take it all in!"
The price is AU$1,606
includes taxes & fees
24 Feb - 25 Feb
Misty Mountain Lodge Pickleball Liberty Ski

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

9.8 out of 10, Exceptional, (74)
"We stayed at the Antietam Toll House on the coldest night in 10 years. Outside temps were 3 degrees Fahrenheit with wind chills less than zero. The cabin provided a cozy respite to a frigid night. It is a charming home in a lovely location next to a stream. Michelle was responsive to our requests. Lots of little details of design that enhanced the stay. We look forward to coming back in summer. "
The price is AU$372
includes taxes & fees
24 Feb - 25 Feb
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

9.6 out of 10, Exceptional, (88)
"It is a very quaint property and sed has the rustic cabin feel, the location was not as intimate as we hoped as it is in a regular neighborhood with close primary with neighbors. "
The price is AU$337
includes taxes & fees
23 Feb - 24 Feb
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Snow is HERE! Only five minutes from Liberty Ski Resort.. Come stay with us!

10.0 out of 10, Exceptional, (291)
"Love this house!"
Snow is HERE! Only five minutes from Liberty Ski Resort.. Come stay with us!

Luxury Getaway on The Potomac

9.6 out of 10, Exceptional, (7)
"My group of friends have started to do an annual getaway trip. This location worked best because of the group size we had, as well as its location being a reasonable distance from where we all live. It lived up to our expectations and and then some! The house was very well maintained and clean and everything was pretty well stocked up in the kitchen as well. Everyone who came loved the home and Melissa was an excellent host. She was very responsive and addressed all of my questions with a prompt...
Luxury Getaway on The Potomac

*In The Heart Of Antietam*

9.6 out of 10, Exceptional, (82)
"House is clean, pleasant with comfortable beds, a serviceable kitchen and nice common space. My husband and 2 adult children were visiting family who live in sharpsburg and their house was pretty full with other visitors. This was a perfect place for us. Highly recommend. "
*In The Heart Of Antietam*

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (17)
"Great experience. Cabin is as shown, very comfortable, easy access. 10 min to Shepherdstown, lots of great restaurants and shops there. Our dates ended up being over the severe cold/snow in January 2025, so we didn't do much hiking or anything on the river, but it was a lovely environment, very peaceful and cozy. Owners were super responsive when needed and very easy to work with. Would definitely go back in nicer weather! "
Charming Cabin in the Woods with River Access

Nice and modern decor, 4BR 3BA, remodeled

10.0 out of 10, Exceptional, (15)
"The location was perfect. I was able to visit several of my family members all who were only 5-10 minutes away. The layout was perfect there was more than enough for everyone to be comfortable. My grandchildren only complaint was that there wasn't a pool on the property or a gas stove 😁. They said breakfast took long to get done. We will definitely be year around occupants. We all enjoyed our stay . "
Nice and modern decor, 4BR 3BA, remodeled

Historic Boonsboro Vacation Rental w/ Grill

9.4 out of 10, Exceptional, (13)
"This place was perfect for us. Secluded and quiet area, great history, and great amenities. It’s definitely a historic cabin and may not be suitable for everyone, especially those who are taller than around 5’9”, or those with physical handicaps. For us it was perfect. The managers were great and communicated with us any time we asked questions. Highly recommend. "
Historic Boonsboro Vacation Rental w/ Grill

Beautiful Mansion in the Country & Wedding Venue

9.8 out of 10, Exceptional, (9)
"The stay and place was awesome and my family and I will definitely be booking again "
The price is AU$4,678
includes taxes & fees
24 Feb - 25 Feb
Beautiful Mansion in the Country & Wedding Venue

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

9.8 out of 10, Exceptional, (53)
"We booked this cabin for a small girls weekend and it was perfect! The view is absolutely amazing! The fireplace is cozy, just make sure you bring lots of wood to keep it going! We also enjoyed using the hot tub each night! The house was clean and in order and communication with Mountain Mama’s was great. "
The price is AU$575
includes taxes & fees
24 Feb - 25 Feb
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
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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Other types of properties in Chewsville you may be interested in

Country Inn & Suites by Radisson, Hagerstown, MD

3.0 star property
8.6 out of 10, Excellent, (1062)
"Excellent"
The price is AU$172
includes taxes & fees
3 Mar - 4 Mar
Country Inn & Suites by Radisson, Hagerstown, MD

Hampton Inn & Suites Frederick-Fort Detrick

2.5 star property
8.8 out of 10, Excellent, (1001)
"The pool was closed due to maintenance the whole weekend. When I booked it didn’t say anything maybe they should update the website."
The price is AU$206
includes taxes & fees
27 Feb - 28 Feb
Hampton Inn & Suites Frederick-Fort Detrick

Liberty Mountain Resort

2.5 star property
8.8 out of 10, Excellent, (426)
"We stayed a Liberty in the main lodge which was beautiful and very quiet. The problem was that Hotels.com doesn't give you the room you book in the pictures. They give you whatever is left at any of the three buildings. We got lucky and got a nice room but it could have been a disaster. Book directly with the resort! "
The price is AU$287
includes taxes & fees
2 Mar - 3 Mar
Liberty Mountain Resort
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.

Frequently asked questions

Are there holiday rentals in Chewsville?

Yes, there are holiday rentals close to the most popular sights in Chewsville, 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 Chewsville has to offer?

Charming "Cream of the Crop" Cape ~❤️of Middletown: This holiday home rental outside of Chewsville offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Chewsville?

Explore the area and family-friendly sights such as Hagerstown Roundhouse Museum, or get out into nature at a spot like Greenbrier State Park. Pennsylvania Dutch Market and Hagerstown Suns Municipal Stadium are a couple of places you'll find in the wider area.

What are holiday rentals like in Chewsville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chewsville. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for small groups.