Pittsfield Vacation Rentals from $105: Search Short-Term Rentals

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

Beautiful Pet friendly cottage by the Stow Ferry : This vacation home rental outside of Pittsfield is located on a lake and has a patio, a garden, and a barbecue grill 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 vacation rentals

A window with a view of a snowy landscape and bare trees.

1. Charming Farmhouse on a working farm.

Pittsfield

Justin S.

$159 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

2. Allegheny River House

Tidioute

Kaleigh M.

$137 nightly

Nov 8 - Nov 9

Total with taxes and fees

A living room with a dark brown leather sofa, a glass coffee table, and a matching armchair. There is a wooden side table with a lamp, a framed picture on the wall, and a door in the background.

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

Warren

Jacklyn

$96 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Warren

Eric S.

$168 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

5. Spacious 2 bedroom apartment

Warren

John S.

$157 nightly

Nov 8 - Nov 9

Total with taxes and fees

A spacious kitchen with wooden cabinets, a marble countertop, and a large island. There is a dining area with a bench and chairs, and a ceiling fan.

6. Eagle's Peak Cottage

Pleasantville

Jacqueline N.

$115 nightly

Nov 8 - Nov 9

Total with taxes and fees

A bedroom with a bed, a desk, a chair, a TV, and a storage unit.

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

Warren

Maura W.

$128 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

8. Sleeps 5 Fully Equipped Apartment Near Golf Courses

Corry

James

$137 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

9. Firefly Suite

Warren

Bonnie

$141 nightly

Nov 8 - Nov 9

Total with taxes and fees

A kitchen with wooden cabinets, a black countertop, a ceiling fan, and a pendant light.

10. Lovely King Ensuite bungalow

Clarendon

Leslie R.

$145 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

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

Tidioute

Brandon C.

$393 nightly

Nov 10 - Nov 11

Total with taxes and fees

12. Homestead Suite

Warren

julia o.

$141 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

13. Allegheny Suite

Warren

Teresa

$141 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

14. Stowaway Suites on the Avenue: Mt Laurel Suite

Warren

James R.

$141 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

15. River view getaway

Warren

Brian H.

$219 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

16. Charming 2-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes

Warren

Bill S.

$489 nightly

Nov 9 - Nov 10

Total with taxes and fees

A room with a striped sofa, a wooden side table with a lamp, and a white dresser.

17. Executive Apartment 1 Bedroom Excellent Location

Corry

Nancy A.

$141 nightly

Dec 1 - Dec 2

Total with taxes and fees

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

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

Tionesta

Kcass 0.

$211 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

Christopher R.

$298 nightly

Nov 8 - Nov 9

Total with taxes and fees

A deck with four Adirondack chairs, a fire pit, and a view of a forested area.

20. Quiet Escape, Peaceful Lake Glimpses

Ashville

Anonymous traveler

$297 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

A large, two-story house with a symmetrical facade, multiple windows, and a well-maintained lawn.

Hazeltine Boutique Hotel BnB

Warren

10/10 Excellent

Carly A

A Holiday Inn Express & Suites hotel with a modern design, featuring a flat roof and a mix of brown and beige exterior walls.

Holiday Inn Express & Suites Jamestown by IHG

Jamestown

10/10 Excellent

We had the pleasure of staying in this hotel on two separate occasions this past July. It was so wonderful on our first trip; there was no question where we'd stay when we returned to Jamestown. You can still smell the "newness" of the hotel in each room. The rooms had impressive new furnishings and were very spacious - we booked a double bed room and suite with a sofa bed, microwave, and small bar sink. The beds were super comfy and the bathrooms were immaculately clean. Free breakfast in the...

BlessedMamaof3

An outdoor dining area with wooden chairs, a table with a fire feature, and a view of a body of water at dusk.

Chautauqua Harbor Hotel - Jamestown

Celoron

10/10 Excellent

More Handicap parking closer to entrance would be nicer. The staff saw me struggling to walk with my cane so a employee ran over with a wheel chair and took me all the way to our room and said we can keep it till we check out. She also went back and found the foot pads for the chair which made it easier to elevate the legs. Also I checked the second day of our stay and asked if I could take the chair with us to see some family in the area and he checked and said ok which was a great help as I...

GREGORY

A modern lobby with a sofa, chairs, a desk, and a large spherical light fixture.

DoubleTree by Hilton Jamestown

Jamestown

10/10 Excellent

Monty

A modern dining area with a long wooden table and yellow chairs, a separate seating area with blue chairs, and a counter with a marble top.

La Quinta Inn & Suites by Wyndham Jamestown

Jamestown

10/10 Excellent

Mark

A hotel room with a bed, a gray sofa with patterned cushions, a round coffee table, and a window with plaid curtains.

Quality Inn & Suites Warren

Warren

10/10 Excellent

Peg

A bedroom with a bed, two bedside tables with lamps, a chair, and two paintings on the wall.

Rest Stop 6 Inn

Tiona

10/10 Excellent

From the outside, this place doesn't look like much, but the rooms have been extensively modernized - everything in my bathroom had was new - and for the money, it's a hidden gem. J.R. is a genial and helpful host - he drew a map giving me a better way to get to my destination that evening - and the Dairy Chalet across the street is tasty nostalgia with more friendly people. They're enough to make you want to move to Tiona, but if that's not in the cards, at least you can stay here as you pass...

Francis

A Tudor-style building with a stone foundation, wooden framing, and a steeply pitched roof.

Peek'n Peak Resort Trademark Collection by Wyndham

Clymer

10/10 Excellent

Laura

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 $105 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.

Frequently Asked Questions

Can I find vacation rentals in Pittsfield?

Yes, you can find vacation rentals close to the most popular local attractions in Pittsfield, or you can go with a more secluded option if you're looking for a relaxing stay.

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

Beautiful Pet friendly cottage by the Stow Ferry: This vacation home rental outside of Pittsfield is located on a lake and has a patio, a garden, and a barbecue grill 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 vacation rentals like in Pittsfield?

Vacation rentals are private properties you can reserve for a couple days or more in Pittsfield. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.

Pittsfield Vacation Rentals

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Upfront pricing

Check prices for these dates

Our top choices for Pittsfield vacation rentals

1. Charming Farmhouse on a working farm.

2. Allegheny River House

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

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

5. Spacious 2 bedroom apartment

6. Eagle's Peak Cottage

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

8. Sleeps 5 Fully Equipped Apartment Near Golf Courses

9. Firefly Suite

10. Lovely King Ensuite bungalow

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

12. Homestead Suite

13. Allegheny Suite

14. Stowaway Suites on the Avenue: Mt Laurel Suite

15. River view getaway

16. Charming 2-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes

17. Executive Apartment 1 Bedroom Excellent Location

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

19. The Refined Retreat

20. Quiet Escape, Peaceful Lake Glimpses

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

Hazeltine Boutique Hotel BnB

10/10 Excellent

Find out more about Pittsfield

Everything you need to know about Pittsfield vacation rentals

Pittsfield vacation rentals: An excellent choice for every season

How to find incredible deals on Pittsfield rentals

Frequently Asked Questions

Can I find vacation rentals in Pittsfield?

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

What can I see and do in Pittsfield?

What are vacation rentals like in Pittsfield?