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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

Superhost

Tiny home in Chester

4.88 out of 5 average rating, 26 reviews

Sage House at Camp Greenwood Vermont w/Sauna

DorothyRating, 5 stars1 week ago
Great place to stay. Very private. Great amenities. Great for solo trip or a couple stay. Head to Ludlow for eats. I’d go back immediately.
Guest favorite

Guesthouse in Cavendish

4.96 out of 5 average rating, 134 reviews

Cozy Cavendish Bunkhouse

AnusheRating, 5 stars4 weeks ago
Sarah and Chris’s home was absolutely adorable and beautifully designed. The cozy and elegant decor made it such a comfortable and inviting stay. Communication was excellent—super responsive and very flexible. I would definitely stay here again. Highly recommend!
Superhost

Apartment in Chester

4.76 out of 5 average rating, 55 reviews

Charming 2 Bdrm near Skiing and Village Green

SarahRating, 5 stars2 months ago
A great place to stay with our dog while in town for a wedding! Walking distance to restaurants and shops. Short drive to beautiful hiking trails. Clean and well-appointed. Definitely recommend!
Guest favorite

Home in Chester

4.98 out of 5 average rating, 42 reviews

Farmhouse w/ views close to skiing sauna EV CHRGR

YuryRating, 5 stars1 month ago
It was fantastic stay! We stayed there with group of 10 friends and it was delightful. The place is stunning (just look at the photos!), super private and feels like a perfect getaway. We had a hike nearby at the lake and then we went to sauna after which was amazing. Miguel is super friendly and responds very quickly. There was ZERO problems, will want to come again!
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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 & traveling professionals

Comfortable accommodations for nomadic and remote working professionals with wifi and dedicated work spaces.

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 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.

Popular amenities for monthly rentals

Kitchen
Wifi
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.
  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Chester
  6. Monthly Rentals