Pittsfield Hotels

  • 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
Feb 2 - Feb 3
Tomorrow
Feb 3 - Feb 4
Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Pittsfield hotels

Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (25)
"Stay at Jimmys is exceptional! From the second you pull into the lot you are greeted with pure joy. Jimmy came out and introduced himself welcoming us to his beautiful Inn. I travel around the globe and have never been welcomed this beautifully in all my life. The property is clean, peaceful, fabulously decorated. It’s so comfortable and welcoming. We didn’t want to leave! And guess what? Jimmy told us we could stay as long as we wanted the day of check out beaches they...
The price is P14,534
P15,988 total
includes taxes & fees
Feb 3 - Feb 4
Stay At Jimmy's
The Shire Woodstock
Property grounds

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (719)
"Lovely place to stay in Woodstock. Great location, clean rooms, and helpful staff"
The price is P8,902
P10,625 total
includes taxes & fees
Feb 4 - Feb 5
The Shire Woodstock
The Vesper
Individually decorated, individually furnished, free WiFi, bed sheets

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (14)
"I loved that this property was within walking distance to all the shops and restaurants in downtown Woodstock "
The price is P10,835
P11,919 total
includes taxes & fees
Feb 5 - Feb 6
The Vesper
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (500)
"Great trip! "
The price is P17,453
P21,767 total
includes taxes & fees
Mar 2 - Mar 3
Woodstock Inn & Resort
The Jackson
Fireplace

The Jackson

4.0 star property
10.0 out of 10, Exceptional, (197)
"The property is quaint and homey. Room was nice but could have had more bathroom amenities, like body lotion."
The price is P13,028
P14,331 total
includes taxes & fees
Feb 3 - Feb 4
The Jackson
506 On the River Inn
Private kitchen

506 On the River Inn

4.0 star property
9.4 out of 10, Exceptional, (956)
"Great, all boxes checked, excellent meal and service"
The price is P11,362
P12,498 total
includes taxes & fees
Feb 3 - Feb 4
506 On the River Inn
Sleep Woodstock Motel
Individually decorated, desk, blackout drapes, iron/ironing board

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (454)
"The suite was lovely and spacious. Perfect for a family trip away"
The price is P5,954
P6,549 total
includes taxes & fees
Feb 3 - Feb 4
Sleep Woodstock Motel
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (94)
"Old fashioned inn with wonderful hosts."
The price is P17,013
P18,544 total
includes taxes & fees
Feb 3 - Feb 4
Echo Lake Inn
My Place Hotel-Randolph VT
Full-size fridge, microwave, stovetop, coffee/tea maker

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (123)
"Nice location"
The price is P6,927
P7,551 total
includes taxes & fees
Feb 19 - Feb 20
My Place Hotel-Randolph VT
Turn of River Lodge
Interior

Turn of River Lodge

2.5 star property
9.0 out of 10, Wonderful, (242)
"Overall my stay was good and for the cost an excellent value for money. My only real criticism is the water does take a long time to get warm so if you are planning to have a shower make sure you turn the water on to heat up well in advance."
The price is P7,384
P8,123 total
includes taxes & fees
Feb 3 - Feb 4
Turn of River Lodge
Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo
Private kitchen

Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo

3.0 star property
The price is P58,532
P99,026 total
includes taxes & fees
Feb 16 - Feb 17
Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo
Northbrook Condo 3 Bedroom Condo
3 bedrooms, free WiFi

Northbrook Condo 3 Bedroom Condo

3.0 star property
The price is P11,492
P36,176 total
includes taxes & fees
Feb 5 - Feb 6
Northbrook Condo 3 Bedroom Condo
Fall Line Condo D1 1 Bedroom Condo
Exterior

Fall Line Condo D1 1 Bedroom Condo

3.5 star property
The price is P28,960
P51,841 total
includes taxes & fees
Feb 17 - Feb 18
Fall Line Condo D1 1 Bedroom Condo
Fall Line Condo C3 1 Bedroom Condo
Private kitchen

Fall Line Condo C3 1 Bedroom Condo

3.5 star property
The price is P29,725
P53,847 total
includes taxes & fees
Feb 28 - Mar 1
Fall Line Condo C3 1 Bedroom Condo
Fall Line Condos by Killington VR - Studios
Aerial view

Fall Line Condos by Killington VR - Studios

2.0 star property
6.0 out of 10, (1)
"Positives: nice atmosphere in our room, beautiful location. Clean, except for 2 items underneath the bed. Negatives: indoor pool closed for summer (ad said it was open), office closed all weekend, some outside areas need paint."
The price is P6,129
P18,103 total
includes taxes & fees
Feb 6 - Feb 7
Fall Line Condos by Killington VR - Studios
Fall Line Condos by Killington VR - 1 Bedrooms
Interior

Fall Line Condos by Killington VR - 1 Bedrooms

3.5 star property
The price is P7,278
P25,772 total
includes taxes & fees
Feb 6 - Feb 7
Fall Line Condos by Killington VR - 1 Bedrooms
Trail Creek by Killington Vacation Rentals
Private kitchen

Trail Creek by Killington Vacation Rentals

3.0 star property
The price is P51,024
P86,117 total
includes taxes & fees
Feb 17 - Feb 18
Trail Creek by Killington Vacation Rentals
Killington Mountain Lodge, Tapestry Collection by Hilton
Terrace/patio

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.2 out of 10, Good, (1007)
"Great stay!"
The price is P15,747
P17,322 total
includes taxes & fees
Feb 24 - Feb 25
Killington Mountain Lodge, Tapestry Collection by Hilton
Whitetail Chalet 4 Bedroom Home
Outdoor spa tub

Whitetail Chalet 4 Bedroom Home

3.0 star property
The price is P16,012
P43,368 total
includes taxes & fees
Feb 3 - Feb 4
Whitetail Chalet 4 Bedroom Home
The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home
Outdoor spa tub

The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home

3.0 star property
The price is P59,527
P103,412 total
includes taxes & fees
Feb 9 - Feb 10
The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home
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
Sign in
Sign up, it's free

Frequently asked questions

Where is the best place to stay in Pittsfield?

Located 14.4 mi (23.2 km) from the heart of Pittsfield, Comfort Inn Rutland - Killington is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Killington Mountain Lodge, Tapestry Collection by Hilton and Mountain Sports Inn. See all available top hotels, or vacation rentals in Pittsfield.

If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable if cancelled before the hotel’s cancellation deadline, which is often 24 or 48 hours before your check-in date. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.

Where can I learn more about changing or cancelling my trip to Pittsfield?

To find more details about changing or cancelling your trip to Pittsfield, go to https://www.expedia.com/service/.

What's the best budget-friendly hotel in Pittsfield?

Based on reviews, Clear River Inn is a popular inn for our travelers who want a more economical choice, and features free WiFi and free parking. View all budget hotels in Pittsfield.

What's the best pet-friendly place to stay in Pittsfield?

Clear River Inn is a top dog-friendly inn, and offers a restaurant and a nightclub for its human guests. See more pet-friendly hotel accommodations in Pittsfield.

What are some accommodations with pools in Pittsfield?

Comfort Inn Rutland - Killington: Provides buffet, an indoor pool, and free self parking. Woodstock Inn & Resort and Days Inn by Wyndham Rutland/Killington Area are a couple of other choices with an onsite pool. View all hotels with pools in Pittsfield.

What's the best accommodation near Rutland Southern Vermont Regional Airport (RUT)?

Comfort Inn Trolley Square is one of the top choices for your stay and is a popular hotel, featuring free breakfast and an indoor pool. It's located 4.9 mi (7.8 km) from Rutland Southern Vermont Regional Airport. Other choices near the airport include Holiday Inn Rutland-Killington Area and Quality Inn Rutland.

What's it like to stay in Pittsfield?

Visitors can enjoy all that Pittsfield has to offer including the bars and restaurants. This city also attracts tourists with its welcoming locals. A top sight in the area is Killington Resort. In Pittsfield, there are 41 hotels and other accommodations to choose from. Find out more about Pittsfield.

What should I see while I'm in Pittsfield?

A favorite place to visit is Green Mountain National Forest. Additionally, you'll find Killington Resort in the area. Check out what more to see and do in Expedia's Pittsfield guide.

What's the seasonal weather like in Pittsfield?

The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches of snowfall.