Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Pittsfield holiday rentals

Fridge, microwave, oven, stovetop
Spacious 2 bedroom apartment

Spacious 2 bedroom apartment

Spacious 2 bedroom apartment
Warren
8.6 out of 10, Excellent, (4 reviews)
"Cherry was an excellent host and responded promptly. The apartment was very clean, well decorated, and comfortable. It had everything we needed. The beds were very comfortable and we slept well. It was in a quiet and safe neighborhood with free parking on the street. We stayed a week to visit with family and friends. We would definitely book here again!"
United States
Teresa B.
The price is HK$655
HK$1,454 total
includes taxes & fees
15 Jan - 16 Jan
Spacious 2 bedroom apartment
Outdoor dining
Riverfront Cabin ★ Views ★ Quiet ★ Fishing ★ Kayak

Riverfront Cabin ★ Views ★ Quiet ★ Fishing ★ Kayak

Riverfront Cabin ★ Views ★ Quiet ★ Fishing ★ Kayak
Tidioute
10.0 out of 10, Exceptional, (43 reviews)
"Very nice place. Easy check-in well stocked kitchen. Fantastic river view and access. "
United States
Darlene a.
The price is HK$765
HK$1,550 total
includes taxes & fees
14 Jan - 15 Jan
Riverfront Cabin ★ Views ★ Quiet ★ Fishing ★ Kayak
Smart TV
Quaint 2 bedroom apartment. 5 minute walk to down town Close to local bike trail

Quaint 2 bedroom apartment. 5 minute walk to down town Close to local bike trail

Quaint 2 bedroom apartment. 5 minute walk to down town Close to local bike trail
Warren
10.0 out of 10, Exceptional, (22 reviews)
"This place was so nice to stay at and very clean. Quiet neighborhood with on street parking that was always close and available. We will definitely stay here again! "
United States
Eric S.
The price is HK$740
HK$1,550 total
includes taxes & fees
14 Jan - 15 Jan
Quaint 2 bedroom apartment. 5 minute walk to down town Close to local bike trail
Exterior
Charming 2-bedroom apartment in peaceful Warren with AC

Charming 2-bedroom apartment in peaceful Warren with AC

Charming 2-bedroom apartment in peaceful Warren with AC
Warren
9.8 out of 10, Exceptional, (11 reviews)
"We found this to be the perfect place to stay when visiting the area to do some hiking in Allegheny National Forest. The apartment was in a historic building downtown, and was very cool. It was clean, spacious, and well-located. We walked to a couple excellent restaurants located nearby (Snuffies and Bent Run Brewery). Very enjoyable stay."
United States
Eric P.
The price is HK$666
HK$905 total
includes taxes & fees
14 Jan - 15 Jan
Charming 2-bedroom apartment in peaceful Warren with AC
Terrace/patio
Relaxing 3 bedroom Pet Friendly Cabin in Scandia

Relaxing 3 bedroom Pet Friendly Cabin in Scandia

Relaxing 3 bedroom Pet Friendly Cabin in Scandia
2.0 star property
Russell
10.0 out of 10, Exceptional, (1 review)
The price is HK$904
HK$1,601 total
includes taxes & fees
15 Jan - 16 Jan
Relaxing 3 bedroom Pet Friendly Cabin in Scandia
Dining
Poland Hill Hideaway, located in the beautiful woods surrounding Tionesta, PA

Poland Hill Hideaway, located in the beautiful woods surrounding Tionesta, PA

Poland Hill Hideaway, located in the beautiful woods surrounding Tionesta, PA
Tionesta
10.0 out of 10, Exceptional, (16 reviews)
"The cabin was clean and beautiful "
United States
Lisa
The price is HK$1,013
HK$1,593 total
includes taxes & fees
15 Jan - 16 Jan
Poland Hill Hideaway, located in the beautiful woods surrounding Tionesta, PA
Interior
Peaceful, Serene, Lake View thru the trees

Peaceful, Serene, Lake View thru the trees

Peaceful, Serene, Lake View thru the trees
2.0 star property
Ashville
10.0 out of 10, Exceptional, (16 reviews)
"It was a calm safe space when we needed one. "
United States
Teresa C.
The price is HK$737
HK$2,189 total
includes taxes & fees
18 Jan - 19 Jan
Peaceful, Serene, Lake View thru the trees
3 bedrooms, WiFi
Allegheny Suite

Allegheny Suite

Allegheny Suite
Warren
9.8 out of 10, Exceptional, (29 reviews)
"Great stay. Hosts communication was great! Would recommend :)"
United States
Emma H.
The price is HK$896
HK$1,160 total
includes taxes & fees
14 Jan - 15 Jan
Allegheny Suite
TV
Allegheny River House

Allegheny River House

Allegheny River House
Tidioute
9.2 out of 10, Wonderful, (10 reviews)
"Wonderful view, pet friendly area, peaceful setting. Host communication was excellent in correcting some check in difficulties."
United States
Cindy I.
The price is HK$526
HK$1,268 total
includes taxes & fees
14 Jan - 15 Jan
Allegheny River House
Smart TV, fireplace, books
River view getaway

River view getaway

River view getaway
Warren
9.8 out of 10, Exceptional, (47 reviews)
"It was a great place to stay!"
United States
Lindsey F.
The price is HK$963
HK$1,856 total
includes taxes & fees
14 Jan - 15 Jan
River view getaway
Exterior
Firefly Suite

Firefly Suite

Firefly Suite
Warren
9.8 out of 10, Exceptional, (13 reviews)
"The property was perfect. Jim did a great job of taking care of us."
United States
James P.
The price is HK$896
HK$1,160 total
includes taxes & fees
14 Jan - 15 Jan
Firefly Suite
1 bedroom, iron/ironing board, free WiFi, bed sheets
Sleeps 5 Fully Equipped Apartment Near Golf Courses

Sleeps 5 Fully Equipped Apartment Near Golf Courses

Sleeps 5 Fully Equipped Apartment Near Golf Courses
Corry
9.4 out of 10, Exceptional, (26 reviews)
"Lovely sunny place. Loved your high ceilings, front window, lace curtains, comfortable seating. Very accommodating. Thank you! "
United States
Leonard M.
The price is HK$694
HK$1,293 total
includes taxes & fees
14 Jan - 15 Jan
Sleeps 5 Fully Equipped Apartment Near Golf Courses
Smart TV
Stowaway Suites on the Avenue: Mt Laurel Suite

Stowaway Suites on the Avenue: Mt Laurel Suite

Stowaway Suites on the Avenue: Mt Laurel Suite
Warren
9.0 out of 10, Wonderful, (12 reviews)
"This place was great! Very clean and convenient. We will absolutely stay again! Parking was a little confusing because the photos are before the pictured fence had grown in with vines but I figured it out. Great stay!"
United States
CodyAnne C.
The price is HK$896
HK$1,160 total
includes taxes & fees
1 Feb - 2 Feb
Stowaway Suites on the Avenue: Mt Laurel Suite
Smart TV, fireplace, books
The Refined Retreat

The Refined Retreat

The Refined Retreat
Celoron
10.0 out of 10, Exceptional, (14 reviews)
"Very nice stay. Well worth it. Cindy is a great host. "
United States
Grace O.
The price is HK$851
HK$2,336 total
includes taxes & fees
20 Jan - 21 Jan
The Refined Retreat
Exterior
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
Chautauqua
10.0 out of 10, Exceptional, (5 reviews)
The price is HK$1,260
HK$3,124 total
includes taxes & fees
14 Jan - 15 Jan
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
TV
Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes

Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes

Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
Warren
The price is HK$702
HK$2,856 total
includes taxes & fees
19 Jan - 20 Jan
Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
Outdoor dining
Charming Resort in the Heart of Bemus Village on CHQ Lake

Charming Resort in the Heart of Bemus Village on CHQ Lake

Charming Resort in the Heart of Bemus Village on CHQ Lake
Bemus Point
10.0 out of 10, Exceptional, (198 reviews)
"The family had a great weekend at the Resort on Main!! Great location in town and just minutes from a drive in the country to enjoy the beautiful colors of Fall Hope to visit again!!"
United States
Josiah S.
The price is HK$1,684
HK$3,937 total
includes taxes & fees
14 Jan - 15 Jan
Charming Resort in the Heart of Bemus Village on CHQ Lake
Microwave, oven, stovetop
Deep Woods Cabin Rentals Cabin #1 Pet Friendly

Deep Woods Cabin Rentals Cabin #1 Pet Friendly

Deep Woods Cabin Rentals Cabin #1 Pet Friendly
2.0 star property
Russell
10.0 out of 10, Exceptional, (1 review)
"Such a cozy stay for Christmas "
United States
Melissa T.
The price is HK$842
HK$1,532 total
includes taxes & fees
25 Jan - 26 Jan
Deep Woods Cabin Rentals Cabin #1 Pet Friendly
Property grounds
Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak

Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak

Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak
Clymer
9.6 out of 10, Exceptional, (10 reviews)
"My family had a wonderful time staying at this condo. It was conveniently close to Peek’n Peak ski resort."
United States
Nathaniel B.
The price is HK$1,442
HK$2,925 total
includes taxes & fees
14 Jan - 15 Jan
Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak
Terrace/patio
Cozy 2-Bedroom Pet-Friendly Cabin – Fully Stocked & Ready for Your Getaway

Cozy 2-Bedroom Pet-Friendly Cabin – Fully Stocked & Ready for Your Getaway

Cozy 2-Bedroom Pet-Friendly Cabin – Fully Stocked & Ready for Your Getaway
2.0 star property
Russell
The price is HK$779
HK$1,463 total
includes taxes & fees
14 Jan - 15 Jan
Cozy 2-Bedroom Pet-Friendly Cabin – Fully Stocked & Ready for Your Getaway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield Hotel Reviews

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

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

10/10 Excellent
"Great setup, well equipped for a snowy weekend with a warm fire and beautiful views of snow covered trees! Gary was great to deal with the few questions we had!"
Jeremy T. 2-night trip
Posted 1 day ago
Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
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Look no further and take a look at our great range of rental properties in Pittsfield!

Frequently asked questions

Can I find holiday rentals in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pittsfield has to offer?

Peaceful Lakefront Cottage - Completely Renovated - Available Year Round!: This holiday home rental outside of Pittsfield is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Pittsfield?

While you're exploring the area, Allegheny River and Buckaloons Recreation Area are a couple of picturesque spots to get outside and enjoy nature. While here, Cornplanter State Forest and Anders Run Natural Area are other places worth a visit.

What are holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for small groups.