Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

West Central Lodging
Exterior
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
Idyllic Mt Sterling Retreat w/ Private Lake!
Interior
Idyllic Mt Sterling Retreat w/ Private Lake!
10.0 out of 10, Exceptional, (3)
"Comfortable and well-equipped home, with more than enough towels. Under-advertised as has 2 1/2 baths, and use of the boathouse. Loved swimming and jumping off the dock, fishing, and just trolling around the lake with the two boats with trolling motors, and the peddle boat. Very wide mowed path around the lake and other trails. Also had marshmallow forks for the s’mores around the campfire. Enjoyed the rocking bench at the end of the dock, especially in the early morning and for watching...
Idyllic Mt Sterling Retreat w/ Private Lake!
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Fridge, microwave, oven, stovetop
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
10.0 out of 10, Exceptional, (43)
"Our family had a great stay in IL. The house was excellent and the llamas were an added entertainment . Would definitely come back to stay!!"
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
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PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Property grounds
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
9.8 out of 10, Exceptional, (66)
"Beautiful, spacious and delightful"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Mississippi River Cabin
Beach
Mississippi River Cabin
9.8 out of 10, Exceptional, (7)
"Last minute rental what is it cozy neat clean cabin."
Mississippi River Cabin
5 Bedroom Lodge in Illinois
Property grounds
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
River Cottage Along the Illinois River.
Exterior
River Cottage Along the Illinois River.
The price is HK$547
per night
31 May - 1 Jun
River Cottage Along the Illinois River.
Buckhorn Barndo &Nature Retreat-near SiloamSprings
Fridge, microwave, oven, stovetop
Buckhorn Barndo &Nature Retreat-near SiloamSprings
Buckhorn Barndo &Nature Retreat-near SiloamSprings
Idyllic Mt Sterling Retreat w/ Private Lake!
Interior
Idyllic Mt Sterling Retreat w/ Private Lake!
2.0 star property
Idyllic Mt Sterling Retreat w/ Private Lake!
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Exterior
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
The price is HK$695
per night
7 May - 8 May
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Buckhorn Barndo Nature Retreat-near Siloamsprings
3 bedrooms, Internet
Buckhorn Barndo Nature Retreat-near Siloamsprings
2.0 star property
Buckhorn Barndo Nature Retreat-near Siloamsprings
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Interior
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
The price is HK$1,008
per night
7 May - 8 May
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
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See all available properties in Pittsfield
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.

Other types of properties in Pittsfield you may be interested in

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Property grounds
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
9.8 out of 10, Exceptional, (66)
"Beautiful, spacious and delightful"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Monroe Street Suites
Lobby sitting area
Monroe Street Suites
2.5 star property
9.6 out of 10, Exceptional, (45)
"Very satisfying experience."
The price is HK$584
per night
7 May - 8 May
Monroe Street Suites
William Watson Hotel
Exterior
William Watson Hotel
3.0 star property
9.0 out of 10, Wonderful, (298)
"This is the most quaint and precious little boutique hotel. It is located right on the square. My room had a perfect view of the local city hall. Both the lobby and my room were decorated with original time-oriented pieces. I absolutely LOVED this place and will definitely stay here again!!"
The price is HK$723
per night
14 May - 15 May
William Watson Hotel
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.

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 holiday rentals in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay. Pittsfield is known for its cafés and entertainment choices. Make sure you have time to check out the breweries and theatres during your trip.

How many holiday rentals are there in Pittsfield?

Choose from 3 Expedia holiday rentals in Pittsfield for a memorable holiday.

What can I see and do in Pittsfield?

Cultural attractions include John Greene Shastid House and Pike County Historic Museum, whereas King Park is one spot to enjoy nature. Old Orchard Country Club and The Eagle's Nest Winery are a couple of places you'll find in the wider area.

What are holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for families.

Recent reviews of Pittsfield properties
Expedia verified reviews

Monroe Street Suites

Monroe Street Suites

5/5 Excellent
"Very satisfying experience."
A verified traveller stayed at Monroe Street Suites
Posted 4 days ago
Monroe Street Suites