Pittsfield Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 16 - Dec 17
Tomorrow
Dec 17 - Dec 18
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Pittsfield vacation rentals

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

Condo in Clymer

Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14
9.8 out of 10, Exceptional, (75)
"Great place to stay!"
United States
Colin S.
The price is ￥27,902
￥60,781 total
includes taxes & fees
Dec 17 - Dec 18
Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14
TV, fireplace
Peaceful Lakefront Cottage - Completely Renovated - Available Year Round!

Vacation Home in Mayville

Peaceful Lakefront Cottage - Completely Renovated - Available Year Round!
10.0 out of 10, Exceptional, (174)
"We enjoyed being with family on the we all grew up on! Peaceful neighborhood and amazing lake view."
United States
Debra R.
Peaceful Lakefront Cottage - Completely Renovated - Available Year Round!
Fridge, microwave, oven, stovetop
Eagle's Peak Cottage

Vacation Home in Pleasantville

Eagle's Peak Cottage
9.0 out of 10, Wonderful, (22)
"We had a great time and will be back again! "
United States
Samantha H.
The price is ￥5,720
￥21,680 total
includes taxes & fees
Dec 21 - Dec 22
Eagle's Peak Cottage
Exterior
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake

Chalet in Mayville

Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake
10.0 out of 10, Exceptional, (245)
"Really great place to get away from it all, my Family truly enjoyed our time there. "
United States
Jody E. M.
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake
Outdoor dining
Prime Location! Ski In/Out. Next to Ski Lift#8, Main Lodge, SugarShack&SportsBar

Condo in Clymer

Prime Location! Ski In/Out. Next to Ski Lift#8, Main Lodge, SugarShack&SportsBar
10.0 out of 10, Exceptional, (74)
"Great stay"
United States
Amy H.
Prime Location! Ski In/Out. Next to Ski Lift#8, Main Lodge, SugarShack&SportsBar
Exterior
Beautiful Peek'n Peak Highlands Condo

Condo in Clymer

Beautiful Peek'n Peak Highlands Condo
10.0 out of 10, Exceptional, (109)
"Place was great and incredibly clean."
United States
Matt P.
Beautiful Peek'n Peak Highlands Condo
Property grounds
Slopeside, ski-in, ski-out condo-perfectly set along run 24 at Peek'n'Peek!

Condo in Clymer

Slopeside, ski-in, ski-out condo-perfectly set along run 24 at Peek'n'Peek!
10.0 out of 10, Exceptional, (11)
"Such a lovely ski in ski out! Very cozy & comfortable. "
United States
Lina P.
Slopeside, ski-in, ski-out condo-perfectly set along run 24 at Peek'n'Peek!
Outdoor dining
Bemus Point Lake Front Cottage with Dock

Vacation Home in Bemus Point

Bemus Point Lake Front Cottage with Dock
9.6 out of 10, Exceptional, (87)
"Nice cottage, well stocked, close to everything. "
United States
Kristin H.
Bemus Point Lake Front Cottage with Dock
Exterior
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

Vacation Home in Chautauqua

20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
10.0 out of 10, Exceptional, (2)
"It was a very clean house with spacious areas including a full apartment upstairs. It was one of the better places we have ever stayed at as far as accommodations go. Highly recommended! Thank you."
United Kingdom
Bill T.
The price is ￥25,050
￥62,463 total
includes taxes & fees
Dec 17 - Dec 18
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
Smart TV, fireplace
Spacious 5-bedroom house with AC, WiFi in charming Bemus Point

Vacation Home in Bemus Point

Spacious 5-bedroom house with AC, WiFi in charming Bemus Point
10.0 out of 10, Exceptional, (6)
"We really enjoyed the house and yard! It worked great for our family gathering! It was a nice walk down to the lake where we spent several evenings watching the sunset from the chairs at the end of the dock."
United States
Bruce F.
Spacious 5-bedroom house with AC, WiFi in charming Bemus Point
1 bedroom, free WiFi, bed sheets
Eagle's Peak Cozy Cabin

Cabin in Pleasantville

Eagle's Peak Cozy Cabin
8.4 out of 10, Very Good, (16)
"Cute cabin would stay again"
United States
Angee K.
Eagle's Peak Cozy Cabin
Exterior
Create your family memories at our nautical lakeside home!

Vacation Home in Ashville

Create your family memories at our nautical lakeside home!
10.0 out of 10, Exceptional, (141)
"This is our 3rd year renting this incredible home. It has everything and anything you may need and so clean! "
United States
Bonnie C.
Create your family memories at our nautical lakeside home!
Property grounds
Chautauqua Lake Front Property - Short Walk to the Village of Bemus Point!

Vacation Home in Bemus Point

Chautauqua Lake Front Property - Short Walk to the Village of Bemus Point!
9.8 out of 10, Exceptional, (110)
"Had a fabulous time, great place"
United States
kathleen w.
Chautauqua Lake Front Property - Short Walk to the Village of Bemus Point!
Property grounds
Quaint historic home in the heart of Bemus Point Village- a stroll to the water!

Vacation Home in Bemus Point

Quaint historic home in the heart of Bemus Point Village- a stroll to the water!
10.0 out of 10, Exceptional, (29)
"Loved our stay in this quaint home! Great location, very clean, plenty of room for our family of six, and included everything we needed for our visit to Bemus Point. Highly recommend! "
United States
Colleen G.
Quaint historic home in the heart of Bemus Point Village- a stroll to the water!
Dining
Cozy camp with an amazing view!

Cabin in Warren

Cozy camp with an amazing view!
2.0 star property
9.6 out of 10, Exceptional, (4)
"Clean, pet friendly, wonderful host. Beautiful property and views."
United States
Nathan M.
Cozy camp with an amazing view!
Exterior
Main St Bemus-HOT TUB-1 Block from Lake

Vacation Home in Ellery

Main St Bemus-HOT TUB-1 Block from Lake
10.0 out of 10, Exceptional, (7)
"This property is an absolute gem! Our young family has stayed in quite a few rental properties in the past, and this one has been the most enjoyable by far. So much to do for the little ones, ample and flexible sleeping arrangements, and the attention to the little things (like the super soft hot tub towels and the s’mores supplies) were the icing on top. Highly recommend this place, and we hope to be back at our next family reunion! "
United States
Alyssa P.
The price is ￥32,960
￥75,079 total
includes taxes & fees
Dec 17 - Dec 18
Main St Bemus-HOT TUB-1 Block from Lake
Smart TV, fireplace
8280 The peak- Hot tub, ski in/ ski out, Pool table, Golf course, fire pit

Vacation Home in Clymer

8280 The peak- Hot tub, ski in/ ski out, Pool table, Golf course, fire pit
10.0 out of 10, Exceptional, (351)
"Great Rental!"
United States
Joe M.
8280 The peak- Hot tub, ski in/ ski out, Pool table, Golf course, fire pit
Exterior
Beautiful Pet friendly cottage by the Stow Ferry

Vacation Home in Ashville

Beautiful Pet friendly cottage by the Stow Ferry
9.4 out of 10, Exceptional, (38)
"House could use a good house cleaning! House was acquitted for our stay. Neighbor in back made a lot of noise. Was very convenient for our stay to get to places!House was pet friendly which was good. Would consider staying again!"
United States
Susan S.
Beautiful Pet friendly cottage by the Stow Ferry
Smart TV, fireplace, books
The Refined Retreat

Vacation Home in Celoron

The Refined Retreat
10.0 out of 10, Exceptional, (13)
"Very clean and organized. Easy in and out. "
United States
scott r.
The price is ￥16,927
￥46,278 total
includes taxes & fees
Dec 17 - Dec 18
The Refined Retreat
Outdoor dining
Prime Location! Ski In/Out. Next to Ski Lift#8, Main Lodge, SugarShack&SportsBar

Condo in Clymer

Prime Location! Ski In/Out. Next to Ski Lift#8, Main Lodge, SugarShack&SportsBar
10.0 out of 10, Exceptional, (17)
"Excellent location and best location! Very comfortable stay and had a wonderful time!"
United States
Kelli K.
Prime Location! Ski In/Out. Next to Ski Lift#8, Main Lodge, SugarShack&SportsBar
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

La Quinta Inn & Suites by Wyndham Jamestown

La Quinta Inn & Suites by Wyndham Jamestown

10/10 Excellent
"Nice hotel"
Mason 1-night trip
Posted 4 days ago
La Quinta Inn & Suites by Wyndham Jamestown

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
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

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?

Peaceful Lakefront Cottage - Completely Renovated - Available Year Round!: This vacation home rental outside of Pittsfield is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 Ashville Bay 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 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.