Pittsfield Holiday Rentals from AU$169: Search Short-Term Rentals

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

Beautiful Pet friendly cottage by the Stow Ferry : This holiday home rental outside of Pittsfield is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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Our top choices for Pittsfield holiday rentals

A room with a brick fireplace, wooden flooring, a dining table with a patterned tablecloth, and a dark wooden cabinet.

1. Charming Farmhouse on a working farm.

Pittsfield

Justin S.

includes taxes & fees

7 Oct - 8 Oct

A street view with two-story brick buildings, one with a storefront and another with a library sign.

2. Charming 2-bedroom apartment in peaceful Warren with AC

Warren

Judith

includes taxes & fees

18 Oct - 19 Oct

A spacious kitchen with a large island, wooden cabinets, and a stone accent wall.

3. Tidioute Riverfront Chalet - Pet Friendly - Across from Game Lands

Tidioute

Brandon C.

includes taxes & fees

7 Oct - 8 Oct

A multi-story building with a courtyard, featuring a parking area and a small outdoor seating area.

4. Firefly Suite

Warren

Colby H.

includes taxes & fees

7 Oct - 8 Oct

A cozy living room with a wooden sofa, a dining table, and a view of a snowy landscape through large sliding glass doors.

5. Allegheny River House

Tidioute

Kaleigh M.

includes taxes & fees

4 Nov - 5 Nov

A living room with a grey sectional sofa, a wooden coffee table, and a patterned rug.

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

Warren

Eric S.

includes taxes & fees

7 Oct - 8 Oct

A room with a four-poster bed, two bedside lamps, a small table with a lamp, and a mirror on the wall.

7. Allegheny Suite

Warren

Teresa

includes taxes & fees

7 Oct - 8 Oct

A living room with a sectional sofa, a coffee table, and a TV.

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

Warren

Bill S.

includes taxes & fees

7 Oct - 8 Oct

A living room with two grey sofas, a coffee table, and a patterned rug.

9. River view getaway

Warren

Lindsey F.

includes taxes & fees

7 Oct - 8 Oct

10. Homestead Suite

Warren

julia o.

includes taxes & fees

15 Oct - 16 Oct

A garden area with a round table and two blue chairs, surrounded by various flowering plants.

11. Charming 1-bedroom apartment in fantastic Warren with AC

Warren

Maura W.

includes taxes & fees

20 Oct - 21 Oct

A living room with a wooden floor, two sofas, a table, and a fireplace.

12. Stowaway Suites on the Avenue: Mt Laurel Suite

Warren

James R.

includes taxes & fees

12 Oct - 13 Oct

A compact kitchen with white cabinetry, a stove, a sink, and a refrigerator.

13. Spacious 2 bedroom apartment

Warren

John S.

includes taxes & fees

18 Oct - 19 Oct

A bedroom with a bed, a chandelier, and a window with curtains.

14. Sleeps 5 Fully Equipped Apartment Near Golf Courses

Corry

Holly Z.

includes taxes & fees

14 Oct - 15 Oct

A metal fire pit with flames, surrounded by grass, with a building in the background.

15. Eagle's Peak Cottage

Pleasantville

Jacqueline N.

includes taxes & fees

7 Oct - 8 Oct

A view from a window overlooking a calm lake surrounded by trees, with a wooden deck in the foreground.

16. Charming 3-bedroom cottage in Russell with AC, WiFi. Enjoy your stay

Russell

deborah k.

includes taxes & fees

17 Oct - 18 Oct

A canal with boats, surrounded by residential houses and greenery.

17. Cozy 2 Bedroom Canal Front Cottage With Private Dock

Ashville

Justin K.

includes taxes & fees

7 Oct - 8 Oct

A campfire with four Adirondack chairs around it, set in a forested area with a picnic table in the background.

18. Quiet Escape, Peaceful Lake Glimpses

Ashville

Sheela J.

includes taxes & fees

12 Oct - 13 Oct

A modern living room with a fireplace, a flat-screen TV, a dining area with a table and chairs, and a kitchen with wooden cabinets and a refrigerator.

19. The Refined Retreat

Celoron

Mary A.

includes taxes & fees

7 Oct - 8 Oct

A wooden interior with a dining area, a sofa, and a staircase.

20. Waterfront Campfires With a Relaxing Creek View. Trout View Cottage near ANF.

Tionesta

Kcass 0.

includes taxes & fees

13 Oct - 14 Oct

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Top Pittsfield Hotel Reviews

Chautauqua Harbor Hotel - Jamestown

10/10 Excellent

"We stay here 4 or more times a year. Comfortable, clean, very professional staff. Great bartender, everyone was well served. Restaurant was busy, so we enjoyed the bar ordering a delicious dinner. Try the Pork chop. Very tasty. Will be back again."

Chautauqua Lake Front Property - Short Walk to the Village of Bemus Point!

10/10 Excellent

"This is the 2nd time the group has stayed at this property, 1st time with current owner. House is pretty much the same as the last time we stayed with the addition of a new wrap around deck on the lake side of the house which is beautiful. We had a party of 10 and it fits all of nicely. Kitchen is well equipped and also has 2 large refrigerators which is needed with a big group. Although the layout upstairs is somewhat tight with 4 bedrooms and only one bathroom, are group never ran into each other both the first time and this time. You spend all your time on the main floor. Location is great being close to Bemus Point and we already plan on coming back next year if we can coordinate everyone's busy schedules. We all enjoyed our visit to this house."

Holiday Inn Express & Suites Jamestown by IHG

10/10 Excellent

"We stay at this location every time we bring our kid to college. It’s become a home away from home. The staff are all always super helpful and so nice. The rooms are great and spacious. Coffee and breakfast downstairs are really good. My only qualm is the walls are on the thinner side so having neighbors who are noisier can be a pain but we live. I have literally zero complaints about the hotel itself."

Find out more about Pittsfield

Everything you need to know about Pittsfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Pittsfield holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield holiday rentals we have selected for you start as low as AU$169 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield holiday 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 holiday.

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.

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?

Beautiful Pet friendly cottage by the Stow Ferry: This holiday home rental outside of Pittsfield is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Pittsfield?

While you're exploring the area, Allegheny River and Karen Bonnell Memorial Park are a couple of picturesque spots to get outside and enjoy nature. While here, Anders Run Natural Area and Cornplanter State Forest 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.

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Check prices for these dates

Our top choices for Pittsfield holiday rentals

1. Charming Farmhouse on a working farm.

2. Charming 2-bedroom apartment in peaceful Warren with AC

3. Tidioute Riverfront Chalet - Pet Friendly - Across from Game Lands

4. Firefly Suite

5. Allegheny River House

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

7. Allegheny Suite

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

9. River view getaway

10. Homestead Suite

11. Charming 1-bedroom apartment in fantastic Warren with AC

12. Stowaway Suites on the Avenue: Mt Laurel Suite

13. Spacious 2 bedroom apartment

14. Sleeps 5 Fully Equipped Apartment Near Golf Courses

15. Eagle's Peak Cottage

16. Charming 3-bedroom cottage in Russell with AC, WiFi. Enjoy your stay

17. Cozy 2 Bedroom Canal Front Cottage With Private Dock

18. Quiet Escape, Peaceful Lake Glimpses

19. The Refined Retreat

20. Waterfront Campfires With a Relaxing Creek View. Trout View Cottage near ANF.

Find holiday rentals that suit your style

Top Pittsfield Hotel Reviews

Chautauqua Harbor Hotel - Jamestown

Eagle's Peak Cottage

Chautauqua Lake Front Property - Short Walk to the Village of Bemus Point!

DoubleTree by Hilton Jamestown

Holiday Inn Express & Suites Jamestown by IHG

Peek'n Peak Resort Trademark Collection by Wyndham

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

Quality Inn & Suites Warren

Bemus Point Vacation Rental

Find out more about Pittsfield

Frequently asked questions

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