Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Pittsfield vacation rentals

Exterior
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Cabin in Pittsfield

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
2.0 star property
The price is ￥39,347
￥54,820 total
includes taxes & fees
Jan 12 - Jan 13
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Dining
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

Cabin in Jacksonville

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
10.0 out of 10, Exceptional, (15)
"Always a nice place to stay."
United States
Pete D.
The price is ￥15,513
￥19,763 total
includes taxes & fees
Jan 11 - Jan 12
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Exterior
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

Vacation Home in Bluffs

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
10.0 out of 10, Exceptional, (58)
"Beautiful place, highly recommend "
United States
Anthony S.
The price is ￥28,065
￥33,398 total
includes taxes & fees
Jan 10 - Jan 11
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Exterior
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Cabin in Jacksonville

Audrey's Abode - Restored log cabin, country setting, minutes from 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 ￥20,214
￥24,744 total
includes taxes & fees
Jan 21 - Jan 22
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Property grounds
Dave’s River House

Cabin in Mozier

Dave’s River House
The price is ￥17,629
￥40,272 total
includes taxes & fees
Jan 15 - Jan 16
Dave’s River House
Interior
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area

Vacation Home in Pleasant Hill

Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
The price is ￥20,214
￥29,229 total
includes taxes & fees
Jan 10 - Jan 11
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Interior
The Yellow Rose Historic Home

Vacation Home in Louisiana

The Yellow Rose Historic Home
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 ￥34,552
￥47,843 total
includes taxes & fees
Jan 11 - Jan 12
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

River's Edge Motel

River's Edge Motel

10/10 Excellent
"Friendly and efficient check-in. Room was clean and fairly modern."
Greg 1-night trip
Posted 2 weeks ago
River's Edge Motel

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:

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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 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 Mississippi River 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.