Title: Browse the Best Pittsfield Resorts from CA $494 | Expedia.ca

[Pittsfield Travel Guide](https://expedia.ca/Pittsfield.dx184066)[Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d184066.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d184066.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d184066.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d184066.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d184066.Destination-Travel-Guides)

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# Search Resort Hotels in Pittsfield from CA $494

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## Check prices for these dates

Next weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Pittsfield Resorts

![The Jewel  | Living area](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/53dd6cd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![The Jewel ](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/369f7f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Mountain Aire Lodge | Private kitchen](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/15f330b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, sun loungers, beach towels, kayaking](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/80a87dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Mountain Top Inn & Resort

Chittenden

9.0/10

Wonderful

(95)

"Absolutely wonderful! The hotel and staff were great. We deeply appreciated the upgrade! No one wanted to leave. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Wendy

CA $453

CA $494 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Chittenden-Hotels-The-Mountain-Top-Inn-Resort.h9673261.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/2ed69ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07d4fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/cd86c3e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Woodstock Inn & Resort

Woodstock

9.2/10

Wonderful

(552)

"Highly recommend stay here"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Margie

CA $473

CA $582 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information)

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

![Comfort Inn Rutland - Killington](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/15d4fef0_y.jpg)

### Comfort Inn Rutland - Killington

10/10 Excellent

"Everything was excellent"

[](https://expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information)

![My Place Hotel-Randolph VT](https://images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/a55aa0fa_y.jpg)

### My Place Hotel-Randolph VT

10/10 Excellent

"Everything was excellent "

[](https://expedia.ca/My-Place-Hotel-Randolph-VT.h105665795.Hotel-Information)

![Days Inn by Wyndham Rutland/Killington Area](https://images.trvl-media.com/lodging/1000000/890000/889600/889570/2b102593_y.jpg)

### Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent

"The food "

[](https://expedia.ca/Rutland-Hotels-Days-Inn-By-Wyndham-RutlandKillington-Area.h889570.Hotel-Information)

![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg)

### Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent

"If you want to travel to Killington with your pup, this is a great spot to stay! Right next to a golf course and other open space for dogs to run. Super friendly staff (Tahoe got lots of treats from the front desk). Great location. Good breakfast. Nice outdoor hot tub for a soak after hitting the nearby slopes."

[](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information)

![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1_y.jpg)

### North Star Lodge and Resort

10/10 Excellent

"Spotless room also very accommodating and friendly! Loved our short stay!"

[](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information)

![Mountain Meadows Lodge](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/7995d81d_y.jpg)

### Mountain Meadows Lodge

10/10 Excellent

"Everything was clean. Staff was extremely nice and helpful. The breakfast was much better than I anticipated. Hot tub and sauna were awesome. Cool little game room. They have telescopes , you can go stargazing with. We had s'mores kits ready to go for you. Very cool place."

[](https://expedia.ca/Killington-Hotels-Mountain-Meadows-Lodge.h894095.Hotel-Information)

![Brandon Inn](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b_y.jpg)

### Brandon Inn

10/10 Excellent

"The room was spotless and nice and warm. Wonderful live music was going on when i arrived. This was my second stay at Brandon Inn. I can't speak highly enough of the place. Very comfortable, clean and reasonably priced. Thank you!"

[](https://expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information)

![Après Inn Killington](https://images.trvl-media.com/lodging/105000000/104900000/104893100/104893073/ae40488d_y.jpg)

### Après Inn Killington

10/10 Excellent

"Location, price, ease of checkin/out."

[](https://expedia.ca/Apres-Inn-Killington.h104893073.Hotel-Information)

![Courtyard Middlebury](https://images.trvl-media.com/lodging/1000000/970000/970000/969917/587431c4_y.jpg)

### Courtyard Middlebury

10/10 Excellent

"care"

[](https://expedia.ca/Middlebury-Hotels-Courtyard-Middlebury.h969917.Hotel-Information)

## Find out more about Pittsfield

## Pittsfield Resorts information

| Number of reviews | 647       |
| ----------------- | --------- |
| Accommodation     | 3 Resorts |
| Lowest Price      | CA $494   |
| Highest Price     | CA $582   |

## Frequently asked questions

### What is Pittsfield like for a resort vacation?

### What's a top resort for my stay in Pittsfield?

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### What's the best way to get to and around Pittsfield?

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