A historic building with a prominent tower and an American flag.

Search Cottages in Pittsfield

  • 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

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

A narrow alleyway between two brick buildings with a green fire escape, a door, and a small outdoor seating area with plants.

1. William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.4 out of 10, Exceptional, (383 reviews)
"Great place"
United States
Caroline
The price is AED 309
AED 340 total
includes taxes & fees
7 Dec - 8 Dec
William Watson Hotel
A two-story building with a flat roof and a large door. There are flower beds with pink flowers in front of the building.

2. Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.8 out of 10, Excellent, (153 reviews)
"Enjoyed our stay at Green Acres! When we return we will definitely stay there again"
United States
Kimberly
The price is AED 433
AED 476 total
includes taxes & fees
6 Dec - 7 Dec
Green Acres Hotel
A modern building with a white exterior, wooden deck, and a pergola with a railing.

3. Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.8 out of 10, Exceptional, (72 reviews)
"Best place Ive stayed period. 100 percent recommend"
United States
Isidro
The price is AED 406
AED 446 total
includes taxes & fees
10 Nov - 11 Nov
Monroe Street Suites
A two-story building with a brick facade, large windows, and a flat roof.

4. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (145 reviews)
"We stay everytime we are in town"
United States
Stephanie
The price is AED 253
AED 278 total
includes taxes & fees
30 Nov - 1 Dec
Rodeway Inn Pittsfield
A covered outdoor seating area with wooden benches and a view of a fenced property.

5. Peaceful Country Escape - High Speed Wifi

Peaceful Country Escape - High Speed Wifi
Pittsfield
The price is AED 551
AED 864 total
includes taxes & fees
20 Nov - 21 Nov
Peaceful Country Escape - High Speed Wifi
A row of multi-story buildings with a variety of storefronts, including a coffee shop and a restaurant.

6. The Eagles Nest Inn

The Eagles Nest Inn
3.0 star property
Louisiana
9.6 out of 10, Exceptional, (28 reviews)
"Cutest place to stay in Louisiana Missouri"
United States
Kimberly
The price is AED 395
AED 449 total
includes taxes & fees
23 Nov - 24 Nov
The Eagles Nest Inn
A two-story building with a flat roof and a covered entrance. There are two cars parked in front, and a truck is visible on the left.

7. River's Edge Motel

River's Edge Motel
2.0 star property
Louisiana
8.8 out of 10, Excellent, (395 reviews)
"Nice location."
United States
Jeff
The price is AED 305
AED 346 total
includes taxes & fees
8 Dec - 9 Dec
River's Edge Motel
A living room with a green sofa, a wooden coffee table, a lamp, and a brick wall with a framed picture.

8. Historic rooms near riverfront in downtown, Louisiana, MO

Historic rooms near riverfront in downtown, Louisiana, MO
Louisiana
10.0 out of 10, Exceptional, (4 reviews)
"Such a cute and comfortable place! Wish I would have found it sooner for my many trips to Missouri!"
United States
Gail
The price is AED 413
AED 497 total
includes taxes & fees
9 Nov - 10 Nov
Historic rooms near riverfront in downtown, Louisiana, MO
A bedroom with a bed, a dresser, a mirror, a television, and a bathroom door.

9. Cozy room located in historic downtown with a 5 minute walk to the riverfront!

Cozy room located in historic downtown with a 5 minute walk to the riverfront!
Louisiana
10.0 out of 10, Exceptional, (2 reviews)
"The host was veey helpful when I had issues with the ap, the room was delightful. Loved dinner at the restaurant next door too!!"
United States
Lori
The price is AED 413
AED 497 total
includes taxes & fees
8 Nov - 9 Nov
Cozy room located in historic downtown with a 5 minute walk to the riverfront!
A wooden deck with a railing, surrounded by trees with autumn foliage.

10. 3-bedroom country home in Pike Co Il with AC and heat

3-bedroom country home in Pike Co Il with AC and heat
Chambersburg
9.6 out of 10, Exceptional, (4 reviews)
"Property had all the amenities needed for a comfortable stay. Very private, quiet setting perfect for a relaxed stay."
United States
Chad L.
The price is AED 459
AED 716 total
includes taxes & fees
21 Nov - 22 Nov
3-bedroom country home in Pike Co Il with AC and heat
A two-story house with a wooden deck and a garden with colorful flowers.

11. COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Bluffs
10.0 out of 10, Exceptional, (65 reviews)
"Very nice property"
United States
Brian G.
The price is AED 658
AED 759 total
includes taxes & fees
8 Nov - 9 Nov
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
A log cabin with a stone chimney, a porch, and a satellite dish.

12. Charming 4-bedroom Sleeps 10 lodge with AC and WiFi in welcoming Nebo

Charming 4-bedroom Sleeps 10 lodge with AC and WiFi in welcoming Nebo
Nebo
10.0 out of 10, Exceptional, (5 reviews)
"Host is super friendly and responds quickly, was very clean and spacious. Will be staying at again in the future!"
United States
Aaron G.
The price is AED 735
AED 1,479 total
includes taxes & fees
3 Dec - 4 Dec
Charming 4-bedroom Sleeps 10 lodge with AC and WiFi in welcoming Nebo
A rustic log cabin with a porch, a red door, and a chimney.

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

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Jacksonville
10.0 out of 10, Exceptional, (28 reviews)
"Really enjoyed our stay. The place was very clean and bed really comfortable "
United States
David W.
The price is AED 400
AED 471 total
includes taxes & fees
8 Nov - 9 Nov
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
A modern house with a large sliding glass door, a brick exterior, and a small attached garage.

14. The Yellow Rose Historic Home

The Yellow Rose Historic Home
Louisiana
9.8 out of 10, Exceptional, (20 reviews)
"Everything was great!"
United States
Brendan R.
The price is AED 909
AED 1,281 total
includes taxes & fees
9 Nov - 10 Nov
The Yellow Rose Historic Home
A bedroom with a bed, a small stool, a wooden wall with a mounted animal head, and a door leading to a bathroom.

15. Sportsman paradise 2 beautiful rooms in Hamburg/mozier Illinois in quiet Calhoun

Sportsman paradise 2 beautiful rooms in Hamburg/mozier Illinois in quiet Calhoun
Hamburg
The price is AED 496
AED 720 total
includes taxes & fees
20 Nov - 21 Nov
Sportsman paradise 2 beautiful rooms in Hamburg/mozier Illinois in quiet Calhoun
A rustic log cabin with a porch and a chimney.

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

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Jacksonville
10.0 out of 10, Exceptional, (19 reviews)
"The place was really neat and the host was incredibly friendly"
United States
Dylan
The price is AED 474
AED 522 total
includes taxes & fees
11 Nov - 12 Nov
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
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

Top Pittsfield Hotel Reviews

William Watson Hotel

William Watson Hotel

10/10 Excellent
"Great place"
Caroline 2-night trip
Posted 5 days ago
William Watson Hotel