Monthly Rentals in Winchester

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

Nearby monthly rentals

Superhost

Tiny home in Winchester

4.88 out of 5 average rating, 113 reviews

The Overlook: A Sweetwater Stay

GiulioRating, 5 stars1 month ago

Patti’s place was delightful, a gorgeous location and beautiful view to the lake.

Apartment in Winchester

4.68 out of 5 average rating, 44 reviews

Beautiful lake side getaway, quiet.

BrittRating, 5 stars2 months ago

Very nice place. The lake is gorgeous. Wish it was warmer, so i could use the kayaks. Bill and Sandie are very friendly and helpful. Their not intrusive at all, but were very responsive to any questions or concerns we had. I would definitely stay here again.

Top guest favorite

Condo in Brattleboro

4.93 out of 5 average rating, 353 reviews

Private & Quiet Studio Apt. in Vermont

LynRating, 5 stars2 weeks ago

We are repeat visitors. Staying here is always a pleasure. The apartment is wonderful. Just as described and perfect for day trips or just staying in. Mary and Lance are friendly and courteous. Hope to be able to stay here again when in the area.

Guest favorite

Camper/RV in Guilford

4.93 out of 5 average rating, 141 reviews

Monadnock Sunrise Forest Hideaway

EthanRating, 5 stars1 day ago

Super nice place!

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 & 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

Destinations to explore

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