Pittsfield Vacation Rentals

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Tonight
Nov 11 - Nov 12
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Nov 12 - Nov 13
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Pittsfield

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

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

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

2.0 star property
Pittsfield
The price is ￥38,524
￥53,998 total
includes taxes & fees
Nov 16 - Nov 17
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
BBQ/picnic area
West Central Lodging

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
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, (15)
"My 2nd stay! I stayed here about 6weeks prior, enroute to visit my daughter at Mizzou. It was so nice that I decided to stay again on my way to her graduation. It was perfect again! It was warm and beautiful in the morning so I even used the outdoor tub."
United States
Kimberly W.
The price is ￥15,189
￥19,350 total
includes taxes & fees
Dec 12 - Dec 13
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Dining
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

Bluffs
10.0 out of 10, Exceptional, (58)
"Beautiful home on the most beautiful property and the most friendly owners! We will be back to stay at this location for sure."
United States
morgan a.
The price is ￥27,478
￥33,348 total
includes taxes & fees
Nov 12 - Nov 13
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Interior
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, (8)
"Quiet and cozy, just what we needed! "
United States
Michelle D.
The price is ￥19,885
￥24,341 total
includes taxes & fees
Nov 12 - Nov 13
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Microwave, oven, stovetop
Dave’s River House

Dave’s River House

Mozier
Dave’s River House
5 bedrooms, desk, travel crib, free WiFi
The Yellow Rose Historic Home

The Yellow Rose Historic Home

Louisiana
9.8 out of 10, Exceptional, (12)
"Lovely older home with lots of charm. We had a big family dinner there and it was wonderful"
United States
Elizabeth W.
The price is ￥37,767
￥52,535 total
includes taxes & fees
Dec 9 - Dec 10
The Yellow Rose Historic Home
Interior
Country Retreat in the heart of Pike County Illinois

Country Retreat in the heart of Pike County Illinois

Nebo
Country Retreat in the heart of Pike County Illinois
House (4 Bedrooms) | Interior
Idyllic Mt Sterling Retreat w/ Private Lake!

Idyllic Mt Sterling Retreat w/ Private Lake!

2.0 star property
Mount Sterling
Idyllic Mt Sterling Retreat w/ Private Lake!
House (1 Bedroom) | Interior
Exotic Animal Farm Stay in Illinois: Tour, Explore

Exotic Animal Farm Stay in Illinois: Tour, Explore

3.0 star property
Kampsville
Exotic Animal Farm Stay in Illinois: Tour, Explore
Property grounds
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 ￥19,791
￥28,617 total
includes taxes & fees
Nov 12 - Nov 13
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Exterior detail
EVERYTHING IS NEW! 3 bedrooms in the county, acreage available

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

2.0 star property
Hamburg
EVERYTHING IS NEW! 3 bedrooms in the county, 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

River's Edge Motel

River's Edge Motel

10/10 Excellent
"Staff was really nice and helpful."
rhonda 1-night trip
Posted 3 days ago
River's Edge Motel

Find out more about Pittsfield

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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 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.