
Apartment holiday rentals in Pittsfield
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Top-rated apartment rentals in Pittsfield
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Popular amenities for Pittsfield apartment rentals
Weekly apartment rentals

Niskayuna One Bedroom Chalet
Tim was an exceptional host. The apartment was clean and centrally located. Would definitely stay there again.

Washington Parkside 1 Bedroom In 1800s Brownstone!
The location is just across the street from the beautiful park, so it is very walkable. The place itself is very clean, cozy and have everything I needed. There are helpful instructions everywhere around the place -- whatever I think I am confused or needed I can always find a help guide right at the spot! Lloyd is also great on communicating. I received plenty instructions and guidance before arrived. Upon arrival, I couldn't get in first time because I turned the door knobe the wrong direction, and Lloyd answered my call in a minute and helped me get in. Overall, great experience! I'll certainly consider here again if I ever pay another visit to Albany.

Downtown Albany 1 Bed + Workstation @ Maiden Lane
place was perfect for my stay and host was very accommodating of my request to extend. would definitely stay again and recommend to others.

Autumn House Minimum stay 3 Days
We had the most relaxing stay at Wendy's apartment! The house was beautifully decorated, so comfortable, and in the best location; just a few minutes away from great shopping and eating. The kitchen was very well furnished if you plan to do any cooking. Wendy is incredibly friendly and generous. She had great recommendations and was easy to get in touch with. We really enjoyed our trip!

Comfortable Stay 2
Jermaine was very helpful and easy to communicate with. The place is just as described. I am familiar with the area, so I was aware of what the surroundings would be like. It was extremely clean and served the purpose for our needs.

Newly renovated 1 bed in Saugerties Village
Very close to the highway for convenience, comfy bed, nice space for a stay with my 2 dogs. There is an active railroad nearby so I recommend a white noise machine for better sleep. I didn't realize the first night until the train went thru about 3 times. The next night I had the white noise machine on and it was much better. Also, though the listing says there is a freezer, there really isn't one. Typical mini fridge freezer but has no door and very very small freezer space. I wasn't paying attention to that detail but the weather was below freezing so I kept my ice packs for my cooler outside to stay frozen. Otherwise, it fit my needs for the weekend and we were comfortable. It was nice to have the yard to walk the dogs. The digital door lock worked well....I've had trouble at other places. I would stay again.

A Lovely Historic Apartment
David’s home was immaculate, spacious and chic, conveniently walkable to all the restaurants and shops downtown. We stayed for a long weekend as we had a wedding nearby; would definitely recommend and stay again!

Warren & 7th St
Austin’s place was centrally located in Hudson. You literally walk out the door and all of the great restaurants and coffee shops are right there. The apartment is spacious, comfortable and met all of our needs. And Austin was very communicative and checked in to make sure all was well.
Private apartment rentals

2 bedroom apart/Village of Athens
Really enjoyed my stay. Great amount of space, rooms were large with lots of storage. Cute kitchen with all the necessities. Close to shops and restaurants. Diane responded quickly with any questions we had and was super friendly.

Lower Warren Street Picture-Perfect 2-Bedroom Apt
You cannot beat the location. It's right in the middle of the heart of Hudson and is also a short walk from the train. The place is cute as well with a nice outdoor space.

West Main
Our second visit to Shirley's place was very enjoyable (just like our earlier trip); this time, a family birthday and other business in the area. As many commenters have noted: lots of personal touches and an apartment that is clean and comfortable beyond expectations. We appreciate the spacious quarters and the privacy and quiet surroundings here, but Shirley's easy to reach if needed. Thanks. We had a wonderful week.

Charming Country Setting
We had a great stay in Ballston spa - Brian was very responsive and made sure we had everything needed for an enjoyable stay. The fenced yard was perfect for our pup and toys in the front closet were a great bonus!

Spacious & Cozy Ground Floor 2/3 Bed private suite
We had a fantastic stay at this Airbnb! The apartment was spotless, stylish, and exactly as described. The location was perfect—close to everything yet quiet at night. The host was responsive and welcoming. Highly recommend this place for anyone looking for a comfortable and convenient stay. We'd definitely return!"

Garden Apartment, on the Park, close to Capital.
We had a great few days staying at James’s apartment, although as we were there for our nephew’s graduation we mainly used the apartment for sleeping. The park across the street made for a peaceful quiet street, and we loved the old brick of the street. Parking was simple as we arrived after the 2hr parking ended for the weekend, and James’s instructions for getting in were simple. The place was super clean and uncluttered. We lived how close it was to Lark Street for dinner. I did have a little trouble with the back neighbors talking outside until the wee hours of the morning, but moved the air purifier to the bedroom for white noise the second night and slept super well after that! Wish we had more time to explore but enjoyed the Savoy Taproom on Lark St and Betty Boop diner a bit farther away!

Main St. Steps to everything. Comfort & Design.
We had a great last-minute getaway! The space was cozy, clean, and full of natural light—perfect for two. The bed was super comfortable, and the kitchen was pristine. Check-in and check-out were simple, and the hosts were friendly and responsive. Great location, just a short drive to nature trails, breweries, and Warren Street. Would definitely stay again!

Adorable Apartment - Near Emma Willard, RPI, Troy
This was such a wonderful stay in Troy! Cheri was so welcoming, and even provided many breakfast foods/snacks which was not expected but very thoughtful and appreciated. The apartment had everything you could need and more. Highly recommended for a stay in this area.
Apartment rentals with a hot tub

Ski-InSki-Out Loft Lift&MT.Views
My stay was smooth and the condo was nice. I was on a business trip so I didn't have much time in the room besides sleeping which was quiet

Saratoga Getaway 2
Victoria and Dave were wonderful hosts! They went out of their way to make us feel welcomed. They were very responsive and everything you could think of was provided for; from cooking essentials to extra treats and towels for the pool. My son loved the pool and walking trail behind the house. We really enjoyed our stay!

Saugerties 2 Bedroom with Hot Tub
Great place to stay for Hits- so close! Everything was as described and the host responded promptly to questions.

SnowTree Chalet- Summer monthly discount 50%
Great location easy walk to the ski resort. Beautifully decorated with a very comfortable king bed. Nice amenities with hot tub and gym.

Mt Snow Condo, 2 Bdrm-Perfect for Remote Work
Great place. Cozy apartment next to Mount Snow. Apartment is clean and has everything you need for a great stay. We used it for a snowboarding trip and would recommend to anyone looking for an apartment next to Mount Snow.

Artsy loft near MassMoCA with pool and hot tubs
We had a great stay at the end of ski season; the place was quiet and relaxing. We will definitely return!

Green Mountain Getaway
Great spot in Mt. Snow! The mountain was extremely accessible and the place is even bigger in person than what it seems in the pictures. Loved our stay here and would definitely come back! Robert and Lindsay were very responsive and made our stay easy!

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
I rented this condo for some of my staff who said their stay was great. Four mechanics sharing a condo at a ski resort, they were easy to please.
Quick stats about flat rentals in Pittsfield
Total rentals
80 properties
Nightly prices starting at
£8 before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
10 properties have a pool
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- Stratton Mountain
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Six Flags New England
- Albany Center Gallery
- Berkshire East Mountain Resort
- Taconic State Park
- Mount Snow Ski Resort
- John Boyd Thacher State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Opus 40
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Kent Falls State Park
- Naumkeag
- Pineridge Cross Country Ski Area
- Beartown State Forest
- Otis Ridge
- Ekwanok Country Club
- Brignole Vineyards