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Compare 8 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Idyllic Mt Sterling Retreat w/ Private Lake!

10.0 out of 10, Exceptional, (5)
"My brother and our families (4 adults, 5 teens) stayed at the Hideaway along with our 2 dogs. Great place! Plenty of comfortable beds for all to have their own space. Living room area and the large dining table was great for playing board games. The dogs (and kids) loved running around in the woods and around the lake. The kitchen is massive, with plenty of room for multiple people to cook and well stocked with every type of pan, utensil or sharp knife you might need! We definitely will...
Idyllic Mt Sterling Retreat w/ Private Lake!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (50)
"We stayed a few nights. House is clean and in very good shape. People are very nice and easy to work with."
The price is AED 716
AED 808 total
includes taxes & fees
3 Feb - 4 Feb
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

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

9.8 out of 10, Exceptional, (71)
"Thanks for having us"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

The Yellow Rose Historic Home

9.8 out of 10, Exceptional, (10)
"Our family had the best time staying in the Yellow Rose! We loved the restored character and mansion feel. There's room for everyone, 2 pianos, lots of board games, a Wii, and a projector for movies. The kitchen was fitted with modern appliances and the tankless water heater means we never ran out of hot water. Comfortable beds too. The game room upstairs was our favorite spot. Carrie is always a pleasure to talk to and she did a great job communicating. Also her tips for places to go were...
The price is AED 900
AED 1,259 total
includes taxes & fees
3 Feb - 4 Feb
The Yellow Rose Historic Home

5 Bedroom Lodge in Illinois

9.8 out of 10, Exceptional, (29)
"Wonderful property, great hosts. We will be back."
5 Bedroom Lodge in Illinois

Cozy 3 bedroom family friendly home in pike county IL

10.0 out of 10, Exceptional, (2)
"The house was older as expected in Pleasant Hill. Very quiet neighborhood and ample space. Stayed three nights everything was as expected. Owners were awesome and responsive. We have booked for two more stays in the fall. Everything is close for groceries. "
Cozy 3 bedroom family friendly home in pike county IL

Buckhorn Barndo &Nature Retreat-near SiloamSprings

Buckhorn Barndo &Nature Retreat-near SiloamSprings

Charming 3-bedroom house in Winchester with WiFi and AC

The price is AED 262
AED 335 total
includes taxes & fees
4 Feb - 5 Feb
Charming 3-bedroom house in Winchester with WiFi and AC

Buckhorn Barndo Nature Retreat-near Siloamsprings

2.0 star property
Buckhorn Barndo Nature Retreat-near Siloamsprings
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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Other property types in Pittsfield

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

9.8 out of 10, Exceptional, (71)
"Thanks for having us"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

2.0 star property
The price is AED 1,025
AED 1,422 total
includes taxes & fees
4 Feb - 5 Feb
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

West Central Lodging

2.5 star property
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. "
West Central Lodging
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.