Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Pittsfield vacation rentals

Exterior

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Pittsfield
The price is CA $343
CA $478 total
includes taxes & fees
May 15 - May 16
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
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, (12 reviews)
"Was an excellent place to stay for the weekend."
United States
Amanda
The price is CA $176
CA $216 total
includes taxes & fees
May 17 - May 18
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Exterior

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Bluffs
10.0 out of 10, Exceptional, (59 reviews)
"Beautiful place, highly recommend "
United States
Anthony S.
The price is CA $245
CA $294 total
includes taxes & fees
May 11 - May 12
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Interior

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

Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Pleasant Hill
The price is CA $176
CA $253 total
includes taxes & fees
May 10 - May 11
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
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, (18 reviews)
"Always a nice place to stay."
United States
Pete D.
The price is CA $135
CA $172 total
includes taxes & fees
Jun 1 - Jun 2
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Interior

The Yellow Rose Historic Home

The Yellow Rose Historic Home
Louisiana
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful place for a family gathering! The kitchen had everything we needed for our meals. The host was kind and welcoming, and the unique historic home was grand and comfortable, with a lot of things for the youngsters to marvel at! We’ll be returning soon! "
United States
Theresa
The price is CA $301
CA $457 total
includes taxes & fees
May 12 - May 13
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

Green Acres Hotel

Green Acres Hotel

10/10 Excellent
"A nice, cozy, small town feel. Was recommended Gianni's pizza down the road from the hotel staff. Very friendly people, will stay again when I visit "
cain 1-night trip
Posted 9 days ago
Green Acres Hotel

Find out more about Pittsfield

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pittsfield. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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 2 Units | Cabin Near Pine Lake | Perfect for Water Fun & Relaxation and Family-Friendly Lakefront Cabin | Water Fun, Fire Rings & Open Lawns.

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 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.