Holiday Homes in Pittsfield

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Pittsfield and around

Buckhorn Barndo &Nature Retreat-near SiloamSprings
Fridge, microwave, oven, stovetop

Buckhorn Barndo &Nature Retreat-near SiloamSprings

Buckhorn Barndo &Nature Retreat-near SiloamSprings
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Terrace/patio

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

9.8 out of 10, Exceptional, (77)
"Fabulous"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
The Yellow Rose Historic Home
5 bedrooms, desk, travel cot, free WiFi

The Yellow Rose Historic Home

10.0 out of 10, Exceptional, (11)
"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"
The price is €275
includes taxes & fees
19 Aug - 20 Aug
The Yellow Rose Historic Home
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Dining

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (55)
"We enjoyed our stay at this beautiful country home. "
The price is €190
includes taxes & fees
19 Aug - 20 Aug
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Spacious 6-bedroom house in rural Versailles with many amenities included.
Exterior

Spacious 6-bedroom house in rural Versailles with many amenities included.

10.0 out of 10, Exceptional, (1)
"We stayed for our Mendota FFA Chapter Officer Retreat. It was very accommodating for our group of nine high school students and two adult chaperones. The house itself is a bit chopped up, but has a lot of charm and many unique decor elements. The bar/kitchen was very unique. We utilized both outdoor grill and firepit area to prepare evening meals. The pool table in the basement was a big hit with the boys. Air fresheners were a little overpowering. "
Spacious 6-bedroom house in rural Versailles with many amenities included.
Idyllic Mt Sterling Retreat w/ Private Lake!
4 bedrooms, bed sheets

Idyllic Mt Sterling Retreat w/ Private Lake!

10.0 out of 10, Exceptional, (7)
"Wonder!! House and lake amazing! Kitchen well stocked with everything one would need! So many outside adventures! We had a wonderful time. Thank you. "
Idyllic Mt Sterling Retreat w/ Private Lake!
Cozy 3 bedroom family friendly home in pike county IL
Exterior

Cozy 3 bedroom family friendly home in pike county IL

10.0 out of 10, Exceptional, (3)
"Clean and nice location"
Cozy 3 bedroom family friendly home in pike county IL
Country Retreat in the heart of Pike County Illinois
Interior

Country Retreat in the heart of Pike County Illinois

Country Retreat in the heart of Pike County Illinois
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 staff and helpful. The room was clean and spacious. It’s a little bit dated but overall nice view and a great staff. We would stay again when in the area. "
Alexis 1-night trip
Posted 8 days ago
River's Edge Motel