Title: Pittsfield Vacation Rentals from $139: Search Short-Term Rentals | Expedia.com

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=553248635975875351&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=553248635975875351&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=553248635975875351&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=553248635975875351&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Pennsylvania%2C+United+States+of+America&regionId=553248635975875351&latLong=41.835614%2C-79.381438&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CABIN)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Pennsylvania%2C+United+States+of+America&regionId=553248635975875351&latLong=41.835614%2C-79.381438&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Pennsylvania%2C+United+States+of+America&regionId=553248635975875351&latLong=41.835614%2C-79.381438&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Pennsylvania%2C+United+States+of+America&regionId=553248635975875351&latLong=41.835614%2C-79.381438&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CONDO)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Pennsylvania%2C+United+States+of+America&regionId=553248635975875351&latLong=41.835614%2C-79.381438&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=COTTAGE)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Pennsylvania%2C+United+States+of+America&regionId=553248635975875351&latLong=41.835614%2C-79.381438&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CHALET)

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## Top Pittsfield Hotel Reviews

![La Quinta Inn & Suites by Wyndham Jamestown](https://images.trvl-media.com/lodging/1000000/980000/978100/978061/3af0ac86_y.jpg)

### La Quinta Inn & Suites by Wyndham Jamestown

10/10 Excellent

"Great experience!"

[](https://expedia.com/Jamestown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Jamestown.h978061.Hotel-Information)

![8409 PEEK N PEAK SLOPE SIDE SKI IN/OUT GOLF LIFT 8,Firepit](https://images.trvl-media.com/lodging/67000000/66110000/66107900/66107872/11fb19fb_y.jpg)

### 8409 PEEK N PEAK SLOPE SIDE SKI IN/OUT GOLF LIFT 8,Firepit

10/10 Excellent

"This was our second stay in this property. Randy offers great communication with his guests and the location is hard to beat! Had a great time here, thanks!"

[](https://expedia.com/Jamestown-Hotels-8409-Peek-N-Peak-Slope-Side-SKI-Inout-Golf-Lift-8.h66107872.Hotel-Information)

![Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake](https://images.trvl-media.com/lodging/34000000/33500000/33492100/33492082/w846h566x1y1-060b6e6a_y.jpg)

### Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake

10/10 Excellent

"The cabin was meticulously built in the most beautiful setting. "

[](https://expedia.com/Mayville-Hotels-Chalet-On-250-Acres.h33492082.Hotel-Information)

![DoubleTree by Hilton Jamestown](https://images.trvl-media.com/lodging/1000000/20000/11500/11426/8fd588ff_y.jpg)

### DoubleTree by Hilton Jamestown

10/10 Excellent

"Yes "

[](https://expedia.com/Jamestown-Hotels-DoubleTree-By-Hilton-Jamestown.h11426.Hotel-Information)

![Chautauqua Harbor Hotel - Jamestown](https://images.trvl-media.com/lodging/24000000/23840000/23832100/23832022/a14ac39d_y.jpg)

### Chautauqua Harbor Hotel - Jamestown

10/10 Excellent

"Easy check-in and beautiful room. We did not expect the beautiful view that came with the room!! 5 Stars!!"

[](https://expedia.com/Celoron-Hotels-Chautauqua-Harbor-Hotel-Jamestown.h23832022.Hotel-Information)

![Peek'n Peak Resort Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/6000000/5270000/5261700/5261672/b2139787_y.jpg)

### Peek'n Peak Resort Trademark Collection by Wyndham

10/10 Excellent

"Room was nice, and clean. Staff was very friendly. "

[](https://expedia.com/Jamestown-Hotels-Peekn-Peak-Resort-Trademark-Collection-By-Wyndham.h5261672.Hotel-Information)

![Peek' n Peak, Camelot  Loft Condo,  Clymer, NY, 250 Yards to Chair 8, Sleeps 14](https://images.trvl-media.com/lodging/74000000/73500000/73496100/73496096/0861e277_y.jpg)

### Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14

10/10 Excellent

"We had a great stay! Perfect condo for a weekend getaway. "

[](https://expedia.com/Clymer-Hotels-Peek-N-Peak.h73496096.Hotel-Information)

![Clarion Pointe Jamestown - Falconer](https://images.trvl-media.com/lodging/1000000/10000/600/559/d3313137_y.jpg)

### Clarion Pointe Jamestown - Falconer

10/10 Excellent

"Clean, comfortable place to stay."

[](https://expedia.com/Jamestown-Hotels-Clarion-Pointe-Jamestown-Falconer.h559.Hotel-Information)

![Quality Inn Falconer - Jamestown](https://images.trvl-media.com/lodging/1000000/490000/482700/482632/9964abc5_y.jpg)

### Quality Inn Falconer - Jamestown

10/10 Excellent

"The entire hotel seemed cleaner than the last time I stayed. I saw a new faces at the front desk so when I checked out, I inquired to as if the management had changed. I was happy to find out that yes it had and that all the riffraff that was hanging at the front door was no longer going to be an issue. As new management had put a stop to it."

[](https://expedia.com/Jamestown-Hotels-Quality-Inn-Falconer-Jamestown.h482632.Hotel-Information)

## Find out more about Pittsfield

**Everything you need to know about Pittsfield vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Pittsfield vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $139 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Pittsfield rentals**

At Expedia, we put the best Pittsfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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- [Vacation Homes in Pittsfield ](https://expedia.com/Pittsfield-Private-Vacation-Homes.d553248635975875351-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Condo Rentals in Pittsfield ](https://expedia.com/Pittsfield-Condos.d553248635975875351-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Pittsfield ](https://expedia.com/Pittsfield-Apartments.d553248635975875351-aaApartments.Travel-Guide-Accommodation)
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## Frequently asked questions

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