Pittsfield Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals 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!

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

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

2.0 star property
The price is AU$495
includes taxes & fees
3 Dec - 4 Dec
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Idyllic Mt Sterling Retreat w/ Private Lake!

10.0 out of 10, Exceptional, (4)
"It was a delightful stay - games on the patio, corn hole on the desk, swimming, fishing, walks, and sitting around the fire. Also, we greatly appreciated the ample fridge and freezer space."
Idyllic Mt Sterling Retreat w/ Private Lake!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (49)
"The house was great and the people were very nice and helpful. "
The price is AU$346
includes taxes & fees
11 Dec - 12 Dec
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

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 AU$539
includes taxes & fees
3 Dec - 4 Dec
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

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

10.0 out of 10, Exceptional, (2)
"Perfect spot for my spouse and I for an overnight stay. Clean and comfortable and just on the outskirts of town. We appreciated and loved the surprise coffee cake! "
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

10.0 out of 10, Exceptional, (2)
"If you’re looking for a peaceful place to rest and recharge, look no further! We thoroughly enjoyed our short stay at Audrey’s Abode! The cabin had everything we needed. The property is quiet and relaxing. We woke up Sunday morning to a beautiful buck right outside the kitchen window. If I could live there, I totally would to get away from the hustle and bustle of our everyday! The town of Jacksonville has everything you want. We did a college tour with our son while we were here and found it...
The price is AU$245
includes taxes & fees
11 Dec - 12 Dec
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Idyllic Mt Sterling Retreat w/ Private Lake!

2.0 star property
Idyllic Mt Sterling Retreat w/ Private Lake!

Exotic Animal Farm Stay in Illinois: Tour, Explore

Exotic Animal Farm Stay in Illinois: Tour, Explore

Exotic Animal Farm Stay in Illinois: Tour, Explore

3.0 star property
Exotic Animal Farm Stay in Illinois: Tour, Explore

Waterfront Cabin: Tranquil Setting in Mozier!

3.0 star property
Waterfront Cabin: Tranquil Setting in Mozier!

Waterfront Cabin: Tranquil Setting in Mozier!

Waterfront Cabin: Tranquil Setting in Mozier!

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.
Don't see what you're looking for?
See all available properties in Pittsfield
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Pittsfield you may be interested in

Rodeway Inn

2.0 star property
6.8 out of 10, (111)
"This motel is more than 70 years old. The owners have made significant upgrades to a very old motel. Room looks nice upon entry and it was impeccably clean. The bed was possibly the best i have encountered in years. What you cant change are 2 foot by 2 foot showers, and a lack of heating controls during the cold months. It's an old central baseboard heating system for the whole operation. Staff was helpful and pleasant. This motel is a good budget option, but its still very old."
The price is AU$103
includes taxes & fees
29 Dec - 30 Dec
Rodeway Inn

William Watson Hotel

3.0 star property
9.0 out of 10, Wonderful, (313)
"Very comfortable, home, atmosphere. The staff was great!!!! Couldn’t ask for a better place to stay!"
The price is AU$195
includes taxes & fees
1 Dec - 2 Dec
William Watson Hotel

Green Acres Hotel

2.5 star property
8.6 out of 10, Excellent, (117)
"Have stayed twice at Green Acres Hotel. Family run. V"
The price is AU$202
includes taxes & fees
29 Nov - 30 Nov
Green Acres 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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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.

What are some of the best holiday rentals that Pittsfield has to offer?

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: This highly rated holiday home rental in Pittsfield is located in a rural location, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Pike County Historic Museum and John Greene Shastid House, 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.