Monthly Rentals in Chester

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

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Nearby monthly rentals

Guest favorite

Home in Chester

5 out of 5 average rating, 29 reviews

Cozy 1850 farmhouse in Stone Village of Chester

YelenaRating, 5 stars1 week ago
Lovely farmhouse that balances the charm of an old rambling house with updated kitchen and bathrooms. Great beds, linens and towels. We love staying at Chester as it’s close enough to Okemo with restaurants that are less packed than Ludlow. Would love to stay here again as it was perfect for our family.
Guest favorite

Guest suite in Chester

4.87 out of 5 average rating, 55 reviews

Adorable, Cozy 2 bedroom apartment walk to village

ChadRating, 5 stars4 days ago
exactly as advertised: Tamera's listing represented our experience. away from road-noise, amenities as listed, location as photographed. good value for us to go skiing for the weekend. thanks, Tamera!
Superhost

Tiny home in Chester

4.9 out of 5 average rating, 30 reviews

Sage House at Camp Greenwood Vermont w/Sauna

EthanRating, 5 stars2 weeks ago
Our stay at Rivage Homeaway's Sage House was lovely! The house was exactly as described and provided the coziest place to stay for a weekend of skiing. Brian and Artemis were extremely responsive and helpful throughout our stay when we had questions, which wasn't often since we had zero issues during our stay. highly recommend and can't wait to come back!
Superhost

Apartment in Windsor

4.71 out of 5 average rating, 28 reviews

Quaint Vermont Village Apartment 2

AndreaRating, 5 stars3 weeks ago
I’ve stayed at Alissa’s places before. This was the first time at this one and it was the same great experience. Location has easy access to highways and amenities. It was quiet, even with the occasional plow. Thanks Alissa! As always, it was great!

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 vacation 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

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.

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

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