Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

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

Griggsville
9.8 out of 10, Exceptional, (80)
"We had the best time staying here. My family of 20 stayed for 3 days and this place was perfect for our trip. The house was large enough to accommodate everyone comfortably and we had everything we needed. The pool area is awesome - everyone had an amazing time from the 2 year old to my 70 year old dad. A great place for kids. Communication was great and the owners were friendly and very helpful. Hope to come back again some day! "
United States
Alison B.
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

West Central Lodging

2.5 star property
Pittsfield
10.0 out of 10, Exceptional, (1)
"We had a wonderful time - very quiet country location, the manager is friendly but not invasive. First time I have heard a whippoorwill sing in many years. "
United States
Anonymous traveller
West Central Lodging

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

Jacksonville
10.0 out of 10, Exceptional, (15)
"This was the cutest and most relaxing a place I have ever stayed. We've so enjoyed our stay."
United States
Linda B.
The price is NZ$222
includes taxes & fees
25 Nov - 26 Nov
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

Bluffs
10.0 out of 10, Exceptional, (58)
"We enjoyed our stay at this beautiful country home. "
United States
Andrea C.
The price is NZ$383
includes taxes & fees
23 Nov - 24 Nov
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

The Yellow Rose Historic Home

Louisiana
9.8 out of 10, Exceptional, (12)
"We are 7 sisters aged 50-76. We had a wonderful stay at the Yellow Rose. This beautiful old home had rooms and beds for all of us. Would definitely stay here again"
United States
Ellen B.
The price is NZ$553
includes taxes & fees
18 Nov - 19 Nov
The Yellow Rose Historic Home

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

Jacksonville
10.0 out of 10, Exceptional, (8)
"The cabin is perfect for creating a relaxing atmosphere. We always like our stay there."
United States
James Z.
The price is NZ$278
includes taxes & fees
1 Dec - 2 Dec
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Dave’s River House

Mozier
The price is NZ$461
includes taxes & fees
16 Dec - 17 Dec
Dave’s River House

Country Retreat in the heart of Pike County Illinois

Nebo
Country Retreat in the heart of Pike County Illinois

Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area

Pleasant Hill
The price is NZ$328
includes taxes & fees
18 Nov - 19 Nov
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area

Idyllic Mt Sterling Retreat w/ Private Lake!

2.0 star property
Mount Sterling
Idyllic Mt Sterling Retreat w/ Private Lake!

Exotic Animal Farm Stay in Illinois: Tour, Explore

3.0 star property
Kampsville
Exotic Animal Farm Stay in Illinois: Tour, Explore

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

2.0 star property
Chambersburg
3-bedroom country home in Pike Co Il with AC and heat

EVERYTHING IS NEW! 3 bedrooms in the country, acreage available

2.0 star property
Hamburg
EVERYTHING IS NEW! 3 bedrooms in the country, acreage available
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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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 favorite 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 depends 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 NZ$222 per night. Entering your travel dates in the search wizard you might find 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

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.

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.