Search Pittsfield hotels

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Filter by

Guest rating
Guest rating
Star rating

Top hotels and accommodation in Pittsfield

Breakfast meal
William Watson Hotel
William Watson Hotel
3.0 star property
9.2 out of 10, Wonderful, (341)
"Great place to stay! Brandi is the best."
United States
Beth
The price is NZ$169
includes taxes & fees
23 Oct - 24 Oct
William Watson Hotel
Free daily on-the-go breakfast
Rodeway Inn
Rodeway Inn
2.0 star property
6.8 out of 10, (121)
"I could not check in because the clerk never showed up to check us in. 2 hours at least with two trips to the site and 3 phone calls. I could not get anyone to talk to or check us in. I left a message that we were cancelling and we went to another motel."
United States
Steve
The price is NZ$116
includes taxes & fees
19 Nov - 20 Nov
Rodeway Inn
Lobby sitting area
Green Acres Hotel
Green Acres Hotel
2.5 star property
8.6 out of 10, Excellent, (139)
"Wonderful stay - was staying with a number of family members and it all worked out"
United States
Richard
The price is NZ$228
includes taxes & fees
28 Oct - 29 Oct
Green Acres Hotel
Comfort Room
Monroe Street Suites
Monroe Street Suites
2.5 star property
9.6 out of 10, Exceptional, (57)
"Definitely one of the best hotels I’ve ever stayed in. Super quiet, clean, convenient, it’s located in town, which there were plenty of shopping and food options. Overall, I would definitely recommend this hotel. And I will be staying there again in the future."
United States
Jake
The price is NZ$225
includes taxes & fees
23 Oct - 24 Oct
Monroe Street Suites
Balcony
River's Edge Motel
River's Edge Motel
2.0 star property
9.0 out of 10, Wonderful, (349)
"Clean,quiet, easy parking and great view of the river."
United States
Edward
The price is NZ$158
includes taxes & fees
23 Oct - 24 Oct
River's Edge Motel
Interior
The Eagles Nest Inn
The Eagles Nest Inn
3.0 star property
9.4 out of 10, Exceptional, (18)
"The room was great. Large and attractive!! Nice bathroom. Had all the convenience you need from TV to mini frig. "
United States
Judith
The price is NZ$185
includes taxes & fees
24 Oct - 25 Oct
The Eagles Nest Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Pittsfield attractions

Old Orchard Country Club

Enjoy a round of golf in Pittsfield at Old Orchard Country Club. Experience the area's entertainment choices and theatre scene.
See properties

Pike County Historic Museum

You can study the exhibits at Pike County Historic Museum, a museum with a storied past, during your travels to Pittsfield. Experience the area's entertainment choices and theatre scene.
See properties

Learn more about Pittsfield

Nestled among rolling hills, Pittsfield invites history buffs to explore the John Greene Shastid House and Pike County Historic Museum. After delving into local heritage, visitors can unwind with a peaceful afternoon at King Park or tee off at nearby Old Orchard Country Club.

See all hotels in Pittsfield
Adobe

Top Pittsfield Hotel Reviews

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

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

10/10 Excellent
"Becky and Dave are excellent hosts. We had the best time. The 3 six year olds brought their bikes and had the best time pretending the front driveway was a race track. If you want to make great memories with your family I would highly recommend this house. "
kelly w. 4-night trip
Posted 2 weeks ago
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

More cheap accommodation in Pittsfield

River's Edge Motel

River's Edge Motel

201 Mansion St, Louisiana, MO
The price is NZ$158 per night from 23 Oct to 24 Oct
NZ$158
23 Oct - 24 Oct
includes taxes & fees
8.8/10 Excellent! (349 reviews)

Frequently asked questions

Where is the best place for a stay in Pittsfield?
Monroe Street Suites is a favourite property for Expedia customers. This hotel offers free parking and free WiFi. Traveller reviews also recommend William Watson Hotel and Green Acres Hotel as top choices for your stay. See all available top hotels, or vacation rentals in Pittsfield.
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. See all vacation rentals in Pittsfield.
If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?
Yes, the majority of room reservations are refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a reservation that's non-refundable, you might be able to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.
What's the best LGBTQ-friendly accommodation in Pittsfield?
William Watson Hotel is a top LGBTQ-friendly hotel that features free parking and a fitness centre. See all available hotels listed as LGBTQ-friendly in Pittsfield.
What's the best dog-friendly place to stay in Pittsfield?
Rodeway Inn is a top hotel for people travelling with their pets and offers free WiFi for its human guests. See more pet-friendly hotel accommodations in Pittsfield.
What are some accommodation options with pools in Pittsfield?
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: Features sunloungers, a pool and complimentary wireless Internet access. View all hotels with pools in Pittsfield.
What's it like to stay in Pittsfield?
Visitors can enjoy all that Pittsfield has to offer, including the cafés, entertainment choices and breweries. Tourists can also enjoy so much more including its theatres. In Pittsfield, there are 10 hotels and other accommodation options to choose from. Find out more about Pittsfield.
What is there to see in Pittsfield?
Cultural venues include Pike County Historic Museum and John Greene Shastid House. A couple of additional sights to add to your itinerary are Old Orchard Country Club and King Park. Take a look at what more there is to see and do in Expedia's Pittsfield guide.
What's the weather like in Pittsfield?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Pittsfield is 1158 mm.

Explore a world of travel with Expedia