Monthly Rentals in Highland Lake

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

Nearby monthly rentals

Top guest favorite
Farm stay in West Simsbury
4.96 out of 5 average rating, 482 reviews

Flamig Farm Staycation

CindyRating, 5 stars1 week ago
My husband and I had a wonderful 3-day stay with our 6 year old granddaughter. She enjoyed making herself at home in the lovely space. Nice deck and grill for eating in the evening. She especially loved all of the animals from the dogs and cats to the emus. She enjoyed learning their names, feeding them and watching l, interacting or tagging along with the owners and various caretakers. Everyone was so kind and welcoming. There is a great playground, various hiking and restaurant options, and a fantastic public library in Simsburg. Highly recommend!
Guest favorite
Apartment in Winchester
4.91 out of 5 average rating, 376 reviews

Gateway to the Berkshires

amberRating, 5 stars4 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 favorite
Home in Colebrook
4.99 out of 5 average rating, 221 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

JoshuaRating, 5 stars2 weeks 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 stars7 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.

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