Title: Pittsfield Vacation Home Rentals from CA $406: Search Top Private Vacation Homes for Rent | 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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# Pittsfield Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Pittsfield Vacation Homes

![Exterior](https://images.trvl-media.com/lodging/108000000/107530000/107521000/107520989/5220a9fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107530000/107521000/107520989/7719248c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107530000/107521000/107520989/fdeff218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107530000/107521000/107520989/be0c8839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Pittsfield

CA $465

CA $1,163 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Pittsfield-Hotels-The-Getaway-Relax-With-Hot-Tub.h107520989.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/a9515c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/w1175h800x25y0-e4bf9cad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/5e456de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/35078f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in North Sherburne

10/10

Exceptional

(1)

"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...

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

Essa R.

CA $260

CA $792 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Pittsfield-Hotels-Peak-Hill-3-Bedroom.h109476281.Hotel-Information)

![House, 4 Bedrooms | Exterior](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550402/3b0a27aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 4 Bedrooms](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550402/0af54003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 4 Bedrooms | Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550402/504f7a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 4 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550402/979ffbf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Pittsfield

CA $580

CA $1,341 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Pittsfield-Hotels-The-Getaway-4-Bedroom-Home.h107550402.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109070000/109068300/109068288/4d73d3c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109070000/109068300/109068288/934eff78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109070000/109068300/109068288/5e59a4cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109070000/109068300/109068288/a7b78e6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Killington

10/10

Exceptional

(5)

"Such a great spot."

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

Kathleen G.

CA $426

CA $1,182 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Killington-Hotels-Alpine-Chalet-Pico.h109068288.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/28e14044.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/5d0199b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/26b11e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, offices](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/72c46fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in North Sherburne

10/10

Exceptional

(22)

"Spacious, clean and cozy home. Perfect for a ski trip or weekend getaway."

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

Darko G.

CA $279

CA $961 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Killington-Hotels-4BR-Killington-Home-Perfect-For-Families.h120663187.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/52000000/51290000/51280800/51280745/2ae285d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51290000/51280800/51280745/b2f27533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/52000000/51290000/51280800/51280745/fb1b77a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/52000000/51290000/51280800/51280745/13bcf3e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Tunbridge

9.8/10

Exceptional

(42)

"Awsome place to stay for a week! "

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

Melinda G.

CA $197

CA $676 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Spacious-Country-Home.h51280745.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/ea91e459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/a40db391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/906f227a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/2fbac199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Killington

8.0/10

Very good

(1)

"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...

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

Dean

CA $167

CA $456 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Killington-Hotels-Luxury-Condo-Tucked-In-The-Heart-Of-Killington.h119097860.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/79000000/78700000/78697400/78697338/5be3dba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78700000/78697400/78697338/70ad246c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78700000/78697400/78697338/02df29f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78700000/78697400/78697338/ec852335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Mount Holly

9.8/10

Exceptional

(20)

"Everything was as expected. Very clean, great location. Would stay again!"

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

Jenna K.

CA $379

CA $747 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Mount-Holly-Hotels-Skilake-House-Hideaway.h78697338.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/49000000/48670000/48666200/48666141/1821527e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48670000/48666200/48666141/756ea176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/49000000/48670000/48666200/48666141/b3ff1fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, smart speakers](https://images.trvl-media.com/lodging/49000000/48670000/48666200/48666141/032adde9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Woodstock

10/10

Exceptional

(29)

"Excellent accommodations! One of the best VRBO’s I’ve ever stayed in. There were 5 women traveling together for a long weekend and Carmen’s place was just the ticket with our own bedrooms and en suite bathrooms. We had the entire place to ourselves and felt very spoiled."

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

kelly f.

CA $1,274

CA $2,062 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Woodstock-Hotels-A-Charming-1820s-Farmhouse.h48666141.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22820000/22817300/22817212/47542658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22820000/22817300/22817212/37ccc647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/23000000/22820000/22817300/22817212/bcfe96ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22820000/22817300/22817212/7cf52872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Killington

10/10

Exceptional

(62)

"Beautiful, modern home, immaculate, great layout, comfortable beds, hot tub was perfect, near Town of Woodstock and Ski Area. Can't imagine a better place to stay!"

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

Howard K.

CA $2,346

CA $3,538 total

includes taxes & fees

Nov 26 - Nov 27

[](https://www.expedia.ca/Killington-Hotels-Luxury.h22817212.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/69000000/68050000/68047700/68047644/161747cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/69000000/68050000/68047700/68047644/9f569e37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68050000/68047700/68047644/b319d1f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68050000/68047700/68047644/5f4e824d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Warren

9.8/10

Exceptional

(39)

"We had a great time staying at this house during our Sugarbush skiing trip this February. The place is easy to access and is close to the ski resort. The house had everything we needed for a comfortable stay. I highly recommend this rental."

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

Dmitriy K.

[](https://www.expedia.ca/Warren-Hotels-Beautiful-Home-Located-In-The-Mad-River-Valley.h68047644.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/0a51ad2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/c88e2df0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/17915502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/f922de49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bridgewater

9.6/10

Exceptional

(17)

"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "

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

Gerri B.

CA $258

CA $781 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Bridgewater-Corners-Hotels-NEW-Blueberry-Hill-Escape-Pet-Friendly-King-Bed-Fire-Pit-Grill.h78342432.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34010000/34007400/34007363/8bd275c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34007400/34007363/7b29efc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34010000/34007400/34007363/d3a96bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007400/34007363/74f69775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Killington

9.6/10

Exceptional

(64)

"We enjoyed the stay. The house was comfortable. Best hot tub we have had in a rental. Location is great."

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

Cheryl K.

CA $330

CA $1,258 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Killington-Hotels-Killington-Mountain-Retreat-Great-Group-Ski-House-Close-To-Resort-Hot-Tub-LIFT-TICKET-DISCOUNTS.h34007363.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108300000/108296500/108296432/4909dc2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108300000/108296500/108296432/f5817cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108300000/108296500/108296432/c90a724b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108300000/108296500/108296432/9b05605e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bomoseen

9.6/10

Exceptional

(4)

"Nice place to stay. Very well equipped and clean."

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

Rich S.

CA $237

CA $771 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Bomoseen-Hotels-The-Bomoseen-Bungalow.h108296432.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100410000/100405300/100405262/533a504d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100410000/100405300/100405262/e0bb8ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100410000/100405300/100405262/5b41c7fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/101000000/100410000/100405300/100405262/dd08d95b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Killington

10/10

Exceptional

(17)

"Clean, comfortable, relaxing; we didnt want to leave!"

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

Karen M.

CA $805

CA $1,644 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Killington-Hotels-Slopeslide-Chalet-Ski-To-And-From-Your-Home.h100405262.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/23000000/22480000/22479200/22479176/1340ba74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/23000000/22480000/22479200/22479176/7adb4eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/23000000/22480000/22479200/22479176/b5820dd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22480000/22479200/22479176/32b5bf72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in granville

9.4/10

Exceptional

(83)

"Great place! Comfortable and conveniently located. "

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

Violet R.

CA $127

CA $428 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Hancock-Hotels-52-Old-Farmhome-Beautiful-Valley-Views-Near-Skiing-Sugarbush.h22479176.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/69000000/68050000/68048900/68048836/7443b3fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/69000000/68050000/68048900/68048836/bed5424c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/69000000/68050000/68048900/68048836/b6bb39a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68050000/68048900/68048836/57f55e25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Killington

10/10

Exceptional

(21)

"Perfect location, easy access to everything, and plenty of space for big groups"

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

Stas T.

CA $487

CA $1,405 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Killington-Hotels-DoubleDen-6br4ba-Entire-House-Great-Location.h68048836.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/c9400bbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/adb899cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/f1b12770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/acc10e06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Killington

10/10

Exceptional

(1)

"Very quiet and private feeling even though it is in a condo like setting. Very clean, and had all the conveniences we needed (A/C, coffee maker, full kitchen appliances). And so kind and personal to leave some souvenirs of the area. We felt very comfortable when every we finished our day of sightseeing to come back to our home away from home. "

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

denise k.

CA $132

CA $406 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Killington-Hotels-CozyDen-AC.h100501897.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/69000000/68210000/68209800/68209745/391cb838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/69000000/68210000/68209800/68209745/89e36b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/69000000/68210000/68209800/68209745/a0113f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68210000/68209800/68209745/a57bbbed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Warren

10/10

Exceptional

(22)

"Had a wonderful stay "

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

Yang O.

[](https://www.expedia.ca/Warren-Hotels-Beautiful-Home-Located-In-The-Mad-River-Valley.h68209745.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100490000/100486600/100486523/9191aba2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/101000000/100490000/100486600/100486523/5a24f435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100490000/100486600/100486523/d9b38c6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/101000000/100490000/100486600/100486523/05db342a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Killington

9.6/10

Exceptional

(14)

"Amazing. So clean. Room for everyone to spread out and enjoy their time."

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

Julianne W.

CA $358

CA $1,116 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Killington-Hotels-BruinsDen-Ski-On-Ski-Off.h100486523.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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Condos

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Chalets

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## Top Pittsfield Hotel Reviews

![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg)

### On The River Inn

10/10 Excellent

"Hands down one of the best places I have ever stayed. Beautiful view, great room and very cozy no matter where you were in the inn."

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

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

### Comfort Inn Rutland - Killington

10/10 Excellent

"Nice place to stay. And they give you a cookie when you check in which was appreciated. "

[](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

"This is a newer hotel with beautiful rooms that include a small kitchenette, with glass top range, garbage disposal and full size fridge. I was very satisfied with the room and the facility as a whole."

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

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

### Mountain Meadows Lodge

10/10 Excellent

"Very cute little hotel. 24 hour on-site staff. Cassie and Brooke are awesome (especially Brooke!!). Friendly staff, clean facilities, hot tub and sauna were great, and pool table, foosball, and dart boards. Room was very cozy and clean. We will be coming back!! 5 mins to Killington. Great breakfast. I’m sure the pond is great in the summer too. 5 star experience!"

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

![The Jackson ](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg)

### The Jackson

10/10 Excellent

"The room was as clean as could be and everyone we met was very friendly. "

[](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information)

![The Mountain Inn at Killington](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg)

### The Mountain Inn at Killington

10/10 Excellent

"We stay here all the time and have no reason to choose anywhere else! Great prices, clean rooms and nice staff. On top of that, the distillery on site makes it so you don't have to leave your hotel at night and drive! Would recommend to anyone who is taking a trip to Killington!"

[](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.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

"Great staff and a beautiful place to stay "

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

![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg)

### Woodstock Inn & Resort

10/10 Excellent

"Clean room, Awesome staff and always a good vibe. "

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

![Sleep Woodstock Motel](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11_y.jpg)

### Sleep Woodstock Motel

10/10 Excellent

"Clean, friendly, easy check in, welcoming accommodations. Can’t wait to come back"

[](https://expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information)

## Find out more about Pittsfield

## Pittsfield Vacation Homes information

| Number of reviews | 409 |
| --- | --- |
| Accommodation | 558 Vacation Homes |
| Lowest Price | CA $406 |
| Highest Price | CA $3,538 |

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-   [Guest Houses in Rochester](https://www.expedia.ca/Rochester-Guest-Houses.d152205-aaGuestHouses.Travel-Guide-Accommodation)
-   [Boutique Hotels in Rochester](https://www.expedia.ca/Rochester-Hotels-Boutique-Hotel.0-0-d152205-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
-   [Golf Hotels in Rochester](https://www.expedia.ca/Rochester-Hotels-Golf-Hotel.0-0-d152205-tGolfHotel.Travel-Guide-Filter-Hotels)
-   [Hotels with a Pool in Rochester](https://www.expedia.ca/Rochester-Hotels-Hotel-With-Pool.0-0-d152205-tHotelwithPool.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Rochester](https://www.expedia.ca/Rochester-Hotels-Luxury-Hotel.0-0-d152205-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Pet-Friendly Hotels in Rochester](https://www.expedia.ca/Rochester-Hotels-Pet-Friendly-Hotel.0-0-d152205-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Ski Hotels in Rochester](https://www.expedia.ca/Rochester-Hotels-Ski-Hotel.0-0-d152205-tSkiHotel.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in Rochester](https://www.expedia.ca/Rochester-Hotels-Spa-Hotel.0-0-d152205-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Rochester Hotels](https://www.expedia.ca/Rochester-Hotels.d152205.Travel-Guide-Hotels)
-   [Treehouses in Rochester](https://www.expedia.ca/Rochester-Treehouses.d152205-aaTreehouses.Travel-Guide-Accommodation)
-   [B&B in Stockbridge](https://www.expedia.ca/Stockbridge-Bed-And-Breakfast.d6357893-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Cheap Hotels in Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-Cheap-Hotels.0-0-d6357893-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Hotels with Balconies in Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-Hotels-With-Balconies.0-0-d6357893-tHotelswithBalconies.Travel-Guide-Filter-Hotels)
-   [Pet-Friendly Hotels in Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-Pet-Friendly-Hotel.0-0-d6357893-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Stockbridge Hotels](https://www.expedia.ca/Stockbridge-Hotels.d6357893.Travel-Guide-Hotels)
-   [Vacation Homes in Stockbridge](https://www.expedia.ca/Stockbridge-Private-Vacation-Homes.d6357893-aaPrivateVacationHomes.Travel-Guide-Accommodation)

-   [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)
-   [Green Mountain National Golf Course](https://www.expedia.ca/Green-Mountain-National-Golf-Course-Killington.d6115884.Vacation-Attraction)
-   [Killington School for Tennis](https://www.expedia.ca/Killington-School-For-Tennis-Killington.d553248621532667625.Vacation-Attraction)
-   [Killington Vacations](https://www.expedia.ca/Killington.d10780.Destination-Travel-Guides)
-   [Visit Killington](https://www.expedia.ca/Killington.dx10780)
-   [Pico Mountain at Killington Ski Resort](https://www.expedia.ca/Pico-Mountain-At-Killington-Ski-Resort-Killington.d6082891.Vacation-Attraction)

-   [Advantage Rent-A-Car Rental Cars in Killington](https://www.expedia.ca/Advantage-Rent-A-Car-Car-Rentals-In-Killington.d10780-c3.Car-Rental-Guide-Suppliers)
-   [Avis Rental Cars in Killington](https://www.expedia.ca/Avis-Car-Rentals-In-Killington.d10780-c41.Car-Rental-Guide-Suppliers)
-   [Car rental Killington](https://www.expedia.ca/Car-Rentals-In-Killington.d10780.Car-Rental-Guide)
-   [Enterprise Rental Cars in Killington](https://www.expedia.ca/Enterprise-Car-Rentals-In-Killington.d10780-c15.Car-Rental-Guide-Suppliers)
-   [Pickup Car Rentals in Killington](https://www.expedia.ca/Pickup-Car-Rentals-In-Killington.d10780-tPickup.Car-Rental-Guide-Class)
-   [Thrifty Car Rental Rental Cars in North Chittenden](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-North-Chittenden.d180850-c45.Car-Rental-Guide-Suppliers)

-   [Killington Vacation Rentals](https://www.expedia.ca/Killington-Vacation-Rentals.d10780.Travel-Guide-VacationRentals)

-   [Book Vacation Homes in Pittsfield on Expedia.com](https://www.expedia.com/Pittsfield-Private-Vacation-Homes.d184066-aaPrivateVacationHomes.Travel-Guide-Accommodation)