Monthly Rentals in Chester

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.

Top Guest favourite

Home in Chester

5 out of 5 average rating, 34 reviews

Cozy 1850 farmhouse in Stone Village of Chester

Kristopher (& Kay)Rating, 5 stars1 week ago

Truly a historic home and a very nice place to stay in the area. Exceptionally well supplied for preparing meals! A big plus for us as we don’t like to eat every meal out. Communicative hosts and pleasant environment, I recommend this location to folks visiting the area!

Guest favourite

Guest suite in Chester

4.89 out of 5 average rating, 62 reviews

Adorable, Cozy 2 bedroom apartment walk to village

MatthewRating, 5 stars2 days ago

Tamera’s place was exactly as listed and then some. Very clean and well kept. The town of Chester was very welcoming and her place is right off the Main Street.

Top Guest favourite

Home in Chester

5 out of 5 average rating, 23 reviews

Historic Gideon Lee House-charming Vermont house

MarionRating, 5 stars3 months ago

Our stay in Chester was fabulous and just what we wanted. It was the perfect combination of relaxing and exploring. Polly and Ian's house is amazing! So beautiful and very nicely decorated. It's a cozy and comfortable place to unwind. The home was immaculate, and the beds were very comfortable. It was a great weekend!

Guest favourite

Guesthouse in Chester

4.92 out of 5 average rating, 176 reviews

Historic Carriage House-20 Min to Okemo-Magic MTN

KaraRating, 5 stars2 months ago

Loved the charming carriage house in Chester! Had everything we needed and more. Would definitely stay there again!

Explore all

The comforts of home and great monthly rates

Fully furnished rentals

From peaceful mountain cabins to convenient urban apartments these furnished rentals have all the amenities of home.

Digital nomads & travelling professionals

Comfortable accommodation for nomadic and remote working professionals, with Wi-Fi and dedicated workspaces.

Delight included

Sometimes the destination is the accommodation. From cliffside cabins to tranquil houseboats, these rentals are full of unique features.

Pets welcome

Discover places to stay that accommodate pets, so you can bring your four-legged friend along.

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.

Popular amenities for monthly rentals

Kitchen

Wi-Fi

Pet friendly

Laptop-friendly workspace

Free parking on premises

Corporate Housing

Stay near Chester's top sights

MacLaomainn's Scottish Pub31 locals recommend

Stone House Antique Center30 locals recommend

Country Girl Diner29 locals recommend

The Pizza Stone VT.26 locals recommend

Lisai's Chester Market Inc17 locals recommend

Stone Hearth Inn & Tavern18 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.