Title: Pittsfield Cottages from CA $261 | 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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## Check prices for these dates

In two weeks

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-07-10&endDate=2026-07-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Pittsfield cottages

![Exterior](https://images.trvl-media.com/lodging/83000000/82970000/82961200/82961114/e1c21b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/83000000/82970000/82961200/82961114/452ffb91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82970000/82961200/82961114/0c83964c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/83000000/82970000/82961200/82961114/27f50440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pristine Custom Cottage, Grand Piano, Massage Studio on Site

[](https://www.expedia.ca/Brandon-Hotels-Luxurious-Secluded-Cottage-Massage-Studio-On-Site.h82961114.Hotel-Information)

Leicester

10/10

Exceptional

(73 reviews)

"Great place to stay for a Vermont getaway! "

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

Jeremy H.

CA $165

CA $261 total

includes taxes & fees

Mar 17 - Mar 18

[](https://www.expedia.ca/Brandon-Hotels-Luxurious-Secluded-Cottage-Massage-Studio-On-Site.h82961114.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/74000000/73730000/73729100/73729008/cd46c0c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/74000000/73730000/73729100/73729008/d64560aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/74000000/73730000/73729100/73729008/b766cbad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/74000000/73730000/73729100/73729008/cb928475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Cabin Retreat

[](https://www.expedia.ca/Roxbury-Hotels-Cottage-Sanctuary-W-High-Speed-Internet-At-Wildwood-Farm.h73729008.Hotel-Information)

Roxbury

10/10

Exceptional

(35 reviews)

"Lovely, quiet & the BEST star gazing!!!"

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

Jill F.

CA $162

CA $292 total

includes taxes & fees

Mar 17 - Mar 18

[](https://www.expedia.ca/Roxbury-Hotels-Cottage-Sanctuary-W-High-Speed-Internet-At-Wildwood-Farm.h73729008.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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## Find vacation rentals that suit your style

Cabins

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Private vacation homes

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America&regionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=COTTAGE)

Apartments

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Condos

[](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America&regionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America&regionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=CHALET)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America&regionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=VILLA)

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## Top Pittsfield Hotel Reviews

![Killington Haus](https://images.trvl-media.com/lodging/124000000/123370000/123364300/123364293/84d48d73_y.jpg)

### Killington Haus

8/10 Good

"Lovely inn close to Killington base. Only challenge was the small bathroom, but having a fridge and a microwave made up for the sight design flaw. We will be back."

[](https://expedia.ca/Killington-Hotels-Killington-Haus.h123364293.Hotel-Information)

![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64_y.jpg)

### On The River Inn

10/10 Excellent

"Had a lovely stay while visiting, enjoyed the breakfast and the staff were all very friendly and accommodating. Would def stay here again"

[](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information)

![My Place Hotel-Randolph VT](https://images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/430b34b8_y.jpg)

### My Place Hotel-Randolph VT

10/10 Excellent

"It was pretty good all around. "

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

![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/17fcad53_y.jpg)

### North Star Lodge and Resort

10/10 Excellent

"First ski weekend getaway, the North star is an absolute gem. It’s like popping back in time where you can appreciate a warm fire, some solo acoustic music and a lively bar. The heated pool does wonders after a hard day skiing."

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

![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/f9bd2dd9_y.jpg)

### Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent

"Great location, hot tub and lobby area. Only thing that would make it better is complimentary breakfast and not charging for parking. "

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

![Best Western Inn & Suites Rutland-Killington](https://images.trvl-media.com/lodging/1000000/20000/16500/16411/9898f616_y.jpg)

### Best Western Inn & Suites Rutland-Killington

10/10 Excellent

"\*"

[](https://expedia.ca/Rutland-Hotels-Best-Western-Inn-Suites-Rutland-Killington.h16411.Hotel-Information)

![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/fae277d0_y.jpg)

### Mountain Sports Inn

10/10 Excellent

"It was great"

[](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information)

![Turn of River Lodge](https://images.trvl-media.com/lodging/19000000/18550000/18540700/18540657/4273b3c6_y.jpg)

### Turn of River Lodge

10/10 Excellent

"Considering this was a lodge atmosphere with shared amenities, the space was clean, in good operating condition, and provided a friendly atmosphere. The staff worked extremely hard to accommodate the patrons!"

[](https://expedia.ca/Killington-Hotels-Turn-Of-River-Lodge.h18540657.Hotel-Information)

![Hampton Inn Rutland](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/5a9cd2d5_y.jpg)

### Hampton Inn Rutland

8/10 Good

"N/A A/C Heat was fine. Parking fine"

[](https://expedia.ca/Rutland-Hotels-Hampton-Inn-Rutland.h1522922.Hotel-Information)

## Find out more about Pittsfield

## Pittsfield Cottages information

| Number of reviews | 108         |
| ----------------- | ----------- |
| Accommodation     | 42 Cottages |
| Lowest Price      | CA $261     |
| Highest Price     | CA $292     |

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- [Flights to Killington ](https://www.expedia.ca/Cheap-Flights-To-Killington.d10780.Travel-Guide-Flights)

- [Fire Tower ](https://www.expedia.ca/Fire-Tower-Killington.d553248621532667609.Vacation-Attraction)
- [Gifford Woods State Park ](https://www.expedia.ca/Gifford-Woods-State-Park-Killington.d6291277.Vacation-Attraction)
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- [Pickup Car Rentals in Killington ](https://www.expedia.ca/Pickup-Car-Rentals-In-Killington.d10780-tPickup.Car-Rental-Guide-Class)

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