Apartment holiday rentals in Pittsfield

Find and book unique apartments on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Pittsfield apartment rentals

Weekly apartment rentals

Top guest favourite
Flat in Niskayuna
5 out of 5 average rating, 133 reviews

Niskayuna One Bedroom Chalet

JimRating, 5 stars4 months ago
Tim was an exceptional host. The apartment was clean and centrally located. Would definitely stay there again.
Top guest favourite
Flat in Albany
4.98 out of 5 average rating, 202 reviews

Washington Parkside 1 Bedroom In 1800s Brownstone!

EvaRating, 5 stars1 week ago
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.
Guest favourite
Flat in Downtown Albany
4.88 out of 5 average rating, 166 reviews

Downtown Albany 1 Bed + Workstation @ Maiden Lane

JeffreyRating, 5 stars1 week ago
place was perfect for my stay and host was very accommodating of my request to extend. would definitely stay again and recommend to others.
Guest favourite
Flat in Hudson
4.97 out of 5 average rating, 59 reviews

Autumn House Minimum stay 3 Days

LaurenRating, 5 stars2 months ago
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!
Superhost
Flat in Troy
4.77 out of 5 average rating, 44 reviews

Comfortable Stay 2

ChristineRating, 5 stars3 weeks ago
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.
Superhost
Flat in Saugerties
4.89 out of 5 average rating, 35 reviews

Newly renovated 1 bed in Saugerties Village

SandyRating, 5 stars4 months ago
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.
Guest favourite
Flat in Hudson
4.97 out of 5 average rating, 199 reviews

A Lovely Historic Apartment

MoriahRating, 5 stars7 months ago
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!
Guest favourite
Flat in Hudson
4.93 out of 5 average rating, 94 reviews

Warren & 7th St

KameronRating, 5 stars5 months ago
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

Superhost
Flat in Athens
4.96 out of 5 average rating, 73 reviews

2 bedroom apart/Village of Athens

KatieRating, 5 stars16 months ago
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.
Top guest favourite
Flat in Hudson
4.98 out of 5 average rating, 176 reviews

Lower Warren Street Picture-Perfect 2-Bedroom Apt

KateRating, 5 stars3 days ago
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.
Top guest favourite
Flat in Canaan
4.99 out of 5 average rating, 138 reviews

West Main

JohnRating, 5 stars2 weeks ago
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.
Guest favourite
Flat in Ballston Spa
4.95 out of 5 average rating, 150 reviews

Charming Country Setting

NatalieRating, 5 stars4 months ago
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!
Superhost
Flat in Shelburne Falls
4.4 out of 5 average rating, 5 reviews

Spacious & Cozy Ground Floor 2/3 Bed private suite

ElminRating, 5 stars3 days ago
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!"
Superhost
Flat in Albany
4.91 out of 5 average rating, 131 reviews

Garden Apartment, on the Park, close to Capital.

ChrisRating, 5 stars12 months ago
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!
Top guest favourite
Flat in Catskill
4.98 out of 5 average rating, 393 reviews

Main St. Steps to everything. Comfort & Design.

StellaRating, 5 stars3 weeks ago
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!
Top guest favourite
Flat in Troy
4.96 out of 5 average rating, 114 reviews

Adorable Apartment - Near Emma Willard, RPI, Troy

AllieRating, 5 stars1 month ago
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

Guest favourite
Flat in Hancock
4.97 out of 5 average rating, 38 reviews

Ski-InSki-Out Loft Lift&MT.Views

ShawnRating, 5 stars3 weeks ago
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
Guest favourite
Flat in Stillwater
5 out of 5 average rating, 20 reviews

Saratoga Getaway 2

SonyaRating, 5 stars9 months ago
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!
Top guest favourite
Flat in Saugerties
5 out of 5 average rating, 8 reviews

Saugerties 2 Bedroom with Hot Tub

JenniferRating, 5 stars9 months ago
Great place to stay for Hits- so close! Everything was as described and the host responded promptly to questions.
Superhost
Flat in Dover
4.87 out of 5 average rating, 15 reviews

SnowTree Chalet- Summer monthly discount 50%

BenignoRating, 5 stars2 weeks ago
Great location easy walk to the ski resort. Beautifully decorated with a very comfortable king bed. Nice amenities with hot tub and gym.
Top guest favourite
Flat in Dover
4.97 out of 5 average rating, 31 reviews

Mt Snow Condo, 2 Bdrm-Perfect for Remote Work

JavierRating, 5 stars1 month ago
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.
Guest favourite
Flat in Hancock
5 out of 5 average rating, 10 reviews

Artsy loft near MassMoCA with pool and hot tubs

NicoleRating, 5 stars1 month ago
We had a great stay at the end of ski season; the place was quiet and relaxing. We will definitely return!
Guest favourite
Flat in Dover
4.83 out of 5 average rating, 24 reviews

Green Mountain Getaway

SophiaRating, 5 stars2 months ago
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!
Superhost
Flat in Hancock
4.72 out of 5 average rating, 18 reviews

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

ShawnRating, 5 stars3 weeks ago
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

Destinations to explore