Monthly Rentals in Chester Gap

Discover long-term rentals that feel like home, for stays of a month or longer.

Nearby monthly rentals

Enter dates and number of guests to see the total trip price including additional fees and taxes, and rounded up to the nearest integer.

Guest favourite
Dome in Front Royal
4.97 out of 5 average rating, 30 reviews

Geodesic Dome~8 acres~Mountain Views from Hot Tub!

MiriamRating, 5 stars2 weeks ago
What a beautiful, peaceful spot — we had a wonderful time staying at Taylor’s dome. Everything is clean, beautiful, and set up with guest comfort and enjoyment in mind. We loved early mornings and late nights on the property and enjoyed its proximity to the beauty of Virginia.
Superhost
Chalet in Chester Gap
4.88 out of 5 average rating, 85 reviews

NEW Hike Wine & Dine! Shenandoah NP & Top Wineries

Raj GopalRating, 5 stars1 week ago
Worth a stay. Host is wonderful and proactive. Would provide all the necessary info even before you ask.
Guest favourite
Apartment in Front Royal
4.94 out of 5 average rating, 16 reviews

BelAir: Private Pristine 2BR Apt Downtown Main St

AndyRating, 5 stars1 week ago
uh what!? I secretly don't want to leave this review so that I can keep this air BNB for just me and my clients! 😉 Gorgeous high ceilings, tons of natural light from the huge windows, literally right on Main Street. This place is the bomb!
Top Guest favourite
Home in Front Royal
4.99 out of 5 average rating, 170 reviews

Idle Hour at Chester Gap

HannahRating, 5 stars1 month ago
Having been to the winery at Chester Gap previously, I knew I wanted to stay in the Airbnb on site. When a girl’s winery trip idea came up, this is exactly where we went! 6 of us stayed very comfortably in his space which was very clean and well stocked. Check in was easy and everything was labeled clearly in the house, with a convenient house book to check as any questions arose. The hot tub was the star of the weekend and we enjoyed relaxing out there at night! The winery is amazing and you can’t beat one that you can walk to. Thank you Jeff for your hospitality, can’t wait to come back!

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term holiday rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Travelling professional? Find a long-term stay with high-speed Wi-Fi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.
*Some exclusions may apply in certain geographies and for some properties.