Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

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

Griggsville
9.8 out of 10, Exceptional, (80)
"A perfect weekend getaway home with loads of fun activities to do. Pool volleyball, pickleball, pool table, basketball court, tennis, etc. This place has it all. The host were helpful on any questions we had and I’m already recommending this place to others. WI’ll be back soon. "
United States
Gregory A.
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 traveler
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.
$119 nightly
The price is $126
Nov 25 - Nov 26
Total with taxes and fees
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.
$205 nightly
The price is $217
Nov 23 - Nov 24
Total with taxes and fees
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.
$308 nightly
The price is $316
Nov 30 - Dec 1
Total with taxes and fees
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.
$149 nightly
The price is $158
Dec 1 - Dec 2
Total with taxes and fees
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Dave’s River House

Mozier
$244 nightly
The price is $258
Dec 17 - Dec 18
Total with taxes and fees
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
$174 nightly
The price is $184
Nov 24 - Nov 25
Total with taxes and fees
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

Newly Updated Home! 3 bedrooms in the country, acreage available

2.0 star property
Hamburg
Newly Updated Home! 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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Top Pittsfield Hotel Reviews

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 $126 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

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 like this Pittsfield vacation home rental. It 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.

What can I see and do in Pittsfield?

Cultural attractions include Pike County Historic Museum and John Greene Shastid House, 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 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.