A historic building with a prominent tower and an American flag.

Pittsfield Vacation Rentals

  • 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

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Pittsfield vacation rentals

Property grounds

1. 3-bedroom country home in Pike Co Il with AC and heat

3-bedroom country home in Pike Co Il with AC and heat
Chambersburg
10.0 out of 10, Exceptional, (2 reviews)
"If you like quiet, wildlife and beautiful trees, this is the perfect place. We loved our stay! Thanks to our host!"
United States
Carol
The price is ￥18,024
￥31,158 total
includes taxes & fees
Sep 5 - Sep 6
3-bedroom country home in Pike Co Il with AC and heat
Dining

2. Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Jacksonville
10.0 out of 10, Exceptional, (25 reviews)
"Really enjoyed our stay. The place was very clean and bed really comfortable "
United States
David W.
The price is ￥15,719
￥20,025 total
includes taxes & fees
Sep 17 - Sep 18
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Interior

3. The Yellow Rose Historic Home

The Yellow Rose Historic Home
Louisiana
9.8 out of 10, Exceptional, (19 reviews)
"Everything was great!"
United States
Brendan R.
The price is ￥39,652
￥59,097 total
includes taxes & fees
Sep 7 - Sep 8
The Yellow Rose Historic Home
Exterior

4. Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Jacksonville
10.0 out of 10, Exceptional, (17 reviews)
"The place was really neat and the host was incredibly friendly"
United States
Dylan
The price is ￥20,483
￥25,073 total
includes taxes & fees
Sep 22 - Sep 23
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
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

Green Acres Hotel

Green Acres Hotel

8/10 Good
"Nice stay, staff was kind. Didn’t have the breakfast. Plenty of parking."
Jennifer 2-night trip
Posted 3 days ago
Green Acres Hotel

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

Are there vacation rentals in Pittsfield?

Yes, you can find vacation rentals near top points of interest in Pittsfield, or you can go with a secluded option if you want a relaxing place to stay. Pittsfield is known for its cafes and entertainment choices. Make sure you have time to check out the breweries and theaters during your trip.

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

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: Visitors give good reviews to this Pittsfield vacation home rental, which is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. Other favorite homes for rent in Pittsfield are Family-Friendly Lakefront Cabin | Water Fun, Fire Rings & Open Lawns and Waterfront Cottage | Steps from Pine Lake & Resort Amenities | Ideal Family Stay.

How many vacation rentals are there in Pittsfield?

Choose from 7 Expedia vacation rentals in Pittsfield for a memorable vacation.

What can I see and do in Pittsfield?

Cultural attractions include John Greene Shastid House and Pike County Historic Museum, whereas King Park is one spot to enjoy nature. Old Orchard Country Club and Clarksville State Game Refuge are a couple of places you'll find in the larger area.

What are vacation rentals like in Pittsfield?

Vacation rentals are privately owned properties you can book for several days or longer in Pittsfield. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family gatherings.