Search Hotels with Air Conditioning in Pittsfield

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Check availability on Pittsfield Hotels with Air Conditioning

Tonight
3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Pittsfield Hotels with Air Conditioning

House, 4 Bedrooms | Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

3.0 star property
Pittsfield
The price is 11.421.958 ₫
25.796.242 ₫ total
includes taxes & fees
4 Dec - 5 Dec
The Getaway 4 Bedroom Home
Front of property
The Jackson

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (256)
"Very cute inn, the restaurant was a plus. Had a great dinner there and def will come back. "
United States
Jaunita
The Jackson
Room 22 | Free WiFi, bed sheets
Kedron Valley Inn

Kedron Valley Inn

3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (326)
"Nice place to stay. Would stay there again & recommend it to friends and family "
United States
Deborah
The price is 5.802.500 ₫
6.382.750 ₫ total
includes taxes & fees
4 Dec - 5 Dec
Kedron Valley Inn
The Jewel | Living area | TV
The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

3.5 star property
Chittenden
9.0 out of 10, Wonderful, (95)
"Absolutely wonderful! The hotel and staff were great. We deeply appreciated the upgrade! No one wanted to leave. "
United States
Wendy
The price is 8.569.925 ₫
9.341.219 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
The Mountain Top Inn & Resort
Terrace/patio
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1009)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is 6.250.875 ₫
7.843.134 ₫ total
includes taxes & fees
5 Dec - 6 Dec
On The River Inn
Property grounds
The Shire Woodstock

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (887)
"Upon entering the hotel, the lobby is gorgeous with 2 fireplaces. Staff was super friendly and the free breakfast was a bonus. The room was spotless and has a fireplace in the room. My wife and I loved this place and will definitely go back. "
United States
Vincent
The price is 3.040.774 ₫
3.545.565 ₫ total
includes taxes & fees
10 Dec - 11 Dec
The Shire Woodstock
Front of property
Stay At Jimmy's

Stay At Jimmy's

3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is 5.248.625 ₫
5.773.489 ₫ total
includes taxes & fees
4 Dec - 5 Dec
Stay At Jimmy's
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (552)
"Highly recommend stay here"
United States
Margie
The price is 8.939.091 ₫
10.993.237 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Woodstock Inn & Resort
Front of property – evening/night
Woodbridge Inn

Woodbridge Inn

3.0 star property
Woodstock
9.6 out of 10, Exceptional, (67)
"Staff was very friendly and welcoming "
United States
Michael
Woodbridge Inn
Deluxe Suite | Individually decorated, desk, blackout curtains, iron/ironing board
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (546)
"Clean, friendly, easy check in, welcoming accommodations. Can’t wait to come back"
United States
David
The price is 2.040.961 ₫
4.328.208 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Sleep Woodstock Motel
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.
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Top Pittsfield Hotel Reviews

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Frequently asked questions

How much do hotels with air conditioning in Pittsfield cost?
Hotels with air conditioning in Pittsfield range between 3.545.565 ₫ and 25.796.242 ₫ per night. These retreats provide the comfort you need at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best hotels with air conditioning in Pittsfield?
Pick from multiple hotels with air conditioning in Pittsfield that have a total average guest review rating of 9.3. Greenbrier Inn is recommended by travellers. This 2-stars hotel also offers individually decorated rooms and pool sun loungers. Mountain Meadows Lodge is another top-rated option with air-conditioned rooms. It has a 3.5-stars rating and amenities such as a firepit and pillow top mattresses.
How many hotels with air conditioning are there in Pittsfield?
Pittsfield has 1 hotels with air-conditioned rooms. To help you find the ideal stay, use our handy filters to search for other amenities or perks you need.
What are the best cheap hotels with air conditioning in Pittsfield?
Hotels with air conditioning start from 3.545.565 ₫ per night, so your Pittsfield escape doesn't need to stretch your budget! Greenbrier Inn is a money-saving option that features many amenities, including pool sun loungers and a garden. Killington Motel is another of our favourite low-cost hotels with AC. Amenities here include WiFi and complimentary breakfast. Exploring free attractions in Pittsfield makes your holiday budget stretch even further. Fire Tower and Lefferts Pond are visitor favourites. With the money you save, why not sightsee some more? This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly hotels with air conditioning in Pittsfield?
Kick back at Mountain Meadows Lodge, a 3.5-stars option just a short drive from downtown. Amenities here include AC, complimentary breakfast and housekeeping services. Another family-friendly hotel with air conditioning is North Star Lodge and Resort. A sauna and a barbecue grill help make this 2-stars property a favourite among guests. Once you've checked in and unpacked your suitcase, there are loads of family-friendly attractions to visit in and around Pittsfield. Fire Tower and Pico Mountain at Killington Ski Resort are two of our top picks.
Why book your hotel with air conditioning in Pittsfield with Expedia?
Holidaying should be simple, so if you're after hotels with air conditioning at a competitive price, Expedia has your back. Save those pennies and select a thrifty stay with AC, or splurge and book a 5-star hotel to spoil your favourite people.
How can I find cheap hotels with air conditioning in Pittsfield?
A great way to locate cheap hotels with air conditioning in Pittsfield is with Expedia's nifty filter tool. First, set your star rating and budget per night, then tick air conditioning under the amenities menu to nab the right place at an impressive price.
What is there to do in Pittsfield near my hotel with air conditioning?
Whatever your tastes or interests, Pittsfield has loads of things to keep you entertained. Pico Mountain at Killington Ski Resort, Pico Peak and Gifford Woods State Park are on many visitors' lists. Don't leave without exploring Fire Tower, Green Mountain National Golf Course and Lefferts Pond either. With Expedia's Pittsfield hotel deals, you can see more wonderful attractions like these with the cash you save.