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

Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Pittsfield holiday rentals

Coffee/tea maker, fridge, microwave, oven

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Griggsville
10.0 out of 10, Exceptional, (81 reviews)
"Wonderful venue with something for everyone to enjoy. "
United States
Karen T.
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Property grounds

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
The price is HK$882
HK$1,525 total
includes taxes & fees
24 Jul - 25 Jul
3-bedroom country home in Pike Co Il with AC and heat
Dining

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, (21 reviews)
"Really enjoyed our stay. The place was very clean and bed really comfortable "
United States
David W.
The price is HK$776
HK$989 total
includes taxes & fees
23 Jul - 24 Jul
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Exterior

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Bluffs
10.0 out of 10, Exceptional, (63 reviews)
"Beautiful place, highly recommend "
United States
Anthony S.
The price is HK$1,404
HK$1,704 total
includes taxes & fees
25 Jul - 26 Jul
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Exterior

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, (15 reviews)
"Was an excellent place to stay for the weekend."
United States
Amanda
The price is HK$1,011
HK$1,238 total
includes taxes & fees
23 Jul - 24 Jul
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Interior

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 HK$1,941
HK$2,798 total
includes taxes & fees
2 Aug - 3 Aug
The Yellow Rose Historic Home
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

William Watson Hotel

William Watson Hotel

10/10 Excellent
"A must stop for any history lover. Beautiful building! AC was sufficient, parking was easy even though the hotel is on a main road. Our room was in the middle of the building so we didn’t hear much road noise. And yes it’s on a main road, but this is a small town so the traffic isn’t anything major. Plus the rooms in the front get lovely views of the old historic courthouse just steps away. Would definitely stay again."
Angela 1-night trip
Posted 2 weeks ago
William Watson 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 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. Pittsfield is known for its cafés and entertainment choices. Make sure you have time to check out the breweries and theatres during your trip.

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

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: This highly rated holiday home rental in Pittsfield is located in a rural location, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. Other favourite homes for rent in Pittsfield are Family-Friendly Lakefront Cabin | Water Fun, Fire Rings & Open Lawns and 2 Units | Cabin Near Pine Lake | Perfect for Water Fun & Relaxation.

How many holiday rentals are there in Pittsfield?

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

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 Riverfront Park are a couple of places you'll find in the wider area.

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 have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for families.