Monthly Rentals in Winchester

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

Nearby monthly rentals

Guest favourite

Apartment in Winchester

4.91 out of 5 average rating, 376 reviews

Gateway to the Berkshires

amberRating, 5 stars3 weeks ago

Very cute little place to stay and have a cozy weekend. Definitely recommend Campbell’s Falls (A hike John recommended to us)

Top guest favourite

Home in Colebrook

4.99 out of 5 average rating, 221 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

JoshuaRating, 5 stars1 week ago

This is at least our 4th time staying at what we call "The Farm" and it is our favorite getaway! We even got my brother to drive 1.5 hours out of his way on his family trip to Boston so he could check it out. A rare gem!

Superhost

Cottage in Winsted

4.89 out of 5 average rating, 35 reviews

Cottage Ease.

KurtRating, 5 stars6 months ago

This cute cottage’s was exactly what we were looking for. Our stay was short but Meredith gave us great suggestions for places to eat to help us avoid wasting our minimal time searching. On a fall weekend the neighborhood was quiet. It was a really nice weekend stay for us.

Top guest favourite

Guest suite in Winchester

4.96 out of 5 average rating, 135 reviews

Private Suite 2 Bedroom Deck Lake Views

DayspringRating, 5 stars2 days ago

Cheryl’s mermaid Haven is the perfect getaway. Not only was it clean and peaceful, the location is perfect for hikes and scenic drives. You will be at ease here. When we had an incident with our car, Cheryl was quick to offer her help. It was such a gift to us. She is the perfect hostess!

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 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

Travelling 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 Winchester's top sights

Burr Pond State Park15 locals recommend

Gilson Cinema & Cafe14 locals recommend

Mario's Tuscany Grill11 locals recommend

Stop & Shop8 locals recommend

Noujaim's Food & Catering5 locals recommend

Little Red Barn Brewers5 locals recommend

Destinations to explore

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