Title: Pittsfield Vacation Home Rentals from CA $130: 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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## Check prices for these dates

In two weeks

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

In two months

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

In three months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Pittsfield vacation homes

![Smart TV, offices](https://images.trvl-media.com/lodging/124000000/123490000/123480200/123480177/e1256054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123490000/123480200/123480177/22b8d20a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/124000000/123490000/123480200/123480177/4c02111a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123490000/123480200/123480177/586cbc8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in North Sherburne

[](https://www.expedia.ca/Pittsfield-Hotels-NEW-Smart-3BR-Basecamp-W-Hot-Tub.h123480177.Hotel-Information)

CA $369

CA $1,001 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Pittsfield-Hotels-NEW-Smart-3BR-Basecamp-W-Hot-Tub.h123480177.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/db902092.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/a7e9e363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/b4888eca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in North Sherburne

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

10/10

Exceptional

(1 review)

"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 $370

CA $1,022 total

includes taxes & fees

Jan 19 - Jan 20

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

![Exterior](https://images.trvl-media.com/lodging/110000000/109080000/109073500/109073427/3e594ac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Toilet paper](https://images.trvl-media.com/lodging/110000000/109080000/109073500/109073427/f6f584ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/110000000/109080000/109073500/109073427/c8e537d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109080000/109073500/109073427/e3fee229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Randolph

[](https://www.expedia.ca/Off-Grid-Glamping-Shed-With-River-Access.h109073427.Hotel-Information)

10/10

Exceptional

(1 review)

CA $81

CA $130 total

includes taxes & fees

Jan 23 - Jan 24

[](https://www.expedia.ca/Off-Grid-Glamping-Shed-With-River-Access.h109073427.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/101000000/100340000/100335500/100335420/5630d307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100340000/100335500/100335420/1b6e3563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100340000/100335500/100335420/22048f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/101000000/100340000/100335500/100335420/c5517e44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Mendon

[](https://www.expedia.ca/Rutland-Hotels-New-2-Bedroom-Close-To-Killington-And-Bike-Trailsthis-Is-Pet-Ok-Downstairs-Unit.h100335420.Hotel-Information)

9.8/10

Exceptional

(6 reviews)

"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."

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

Aurore H.

CA $179

CA $390 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Rutland-Hotels-New-2-Bedroom-Close-To-Killington-And-Bike-Trailsthis-Is-Pet-Ok-Downstairs-Unit.h100335420.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/69000000/68050000/68047700/68047644/ea8293f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/69000000/68050000/68047700/68047644/950782f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/69000000/68050000/68047700/68047644/d846c2c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/69000000/68050000/68047700/68047644/4c80752a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Warren

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

9.6/10

Exceptional

(40 reviews)

"The place was spacious, but small, which I loved! Plenty of hot water, great communication with owner, plenty of extra chairs and the leaf for the table was fantastic!"

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

Michael M.

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

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/244b8f71.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/e40e49c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/0b045033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/809fbf0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bridgewater

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

9.6/10

Exceptional

(17 reviews)

"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 $292

CA $818 total

includes taxes & fees

Jan 21 - Jan 22

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

![Marina](https://images.trvl-media.com/lodging/109000000/108300000/108296500/108296432/8a1f7483.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/a08030b2.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)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108300000/108296500/108296432/a8de2dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bomoseen

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

9.6/10

Exceptional

(4 reviews)

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

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

Rich S.

CA $232

CA $761 total

includes taxes & fees

Jan 19 - Jan 20

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

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

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/b023884e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/5b8a97be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Killington

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

10/10

Exceptional

(1 review)

"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 $167

CA $449 total

includes taxes & fees

Jan 19 - Jan 20

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/8ba7a989.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)

![TV](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/151a7dcc.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)

### Vacation Home in Killington

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

8.0/10

Very good

(1 review)

"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 $230

CA $537 total

includes taxes & fees

Jan 27 - Jan 28

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

![Exterior](https://images.trvl-media.com/lodging/69000000/68210000/68209800/68209745/d5ee2388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/69000000/68210000/68209800/68209745/697e0748.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)

![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)

### Vacation Home in Warren

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

10/10

Exceptional

(23 reviews)

"Fantastic house in a beautiful setting. Just right for the area and the kind of trip we were hoping to have. Colin is a great host as well."

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

kevin m.

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

![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35370000/35361300/35361208/b635093d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35370000/35361300/35361208/921092b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/36000000/35370000/35361300/35361208/d7bc9b42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35370000/35361300/35361208/f2b8cc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Warren

[](https://www.expedia.ca/Warren-Hotels-Classic-Vermont-Farmhouse-Near-Sugarbush-Resort.h35361208.Hotel-Information)

9.6/10

Exceptional

(45 reviews)

"Charming older home, clearly well loved. Enjoyed eating on the back porch, the generous living room space, and the sinks in every bedroom!"

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

Nathalie B.

[](https://www.expedia.ca/Warren-Hotels-Classic-Vermont-Farmhouse-Near-Sugarbush-Resort.h35361208.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/91000000/90300000/90299400/90299304/5b91f69f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90300000/90299400/90299304/78db4a66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/91000000/90300000/90299400/90299304/cfb34b80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90300000/90299400/90299304/ab1b951c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Warren

[](https://www.expedia.ca/Warren-Hotels-Beautiful-Home-Located-In-The-Mad-River-Valley.h90299304.Hotel-Information)

9.4/10

Exceptional

(8 reviews)

"Good area"

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

Dakota N.

[](https://www.expedia.ca/Warren-Hotels-Beautiful-Home-Located-In-The-Mad-River-Valley.h90299304.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122590000/122582200/122582186/87e5dd2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122590000/122582200/122582186/6d334060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122590000/122582200/122582186/aa5fb10c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122590000/122582200/122582186/9ba7459a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Brookfield

[](https://www.expedia.ca/Brookfield-Hotels-Vermont-Retreat-3BR-With-Mountain-Views-And-Trails.h122582186.Hotel-Information)

CA $278

CA $827 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Brookfield-Hotels-Vermont-Retreat-3BR-With-Mountain-Views-And-Trails.h122582186.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/6f79e5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/583d8f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/edbb7161.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/ebda3bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Killington

[](https://www.expedia.ca/Killington-Hotels-Fun-In-Fun-Out-Ski-Home-Main-Floor-Renovated-3BR2BA-Hot-Tub-Lift-Tickets.h105777639.Hotel-Information)

10/10

Exceptional

(1 review)

"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "

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

Catherine S.

CA $320

CA $964 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Killington-Hotels-Fun-In-Fun-Out-Ski-Home-Main-Floor-Renovated-3BR2BA-Hot-Tub-Lift-Tickets.h105777639.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/111000000/110270000/110263700/110263621/4a9f4ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110270000/110263700/110263621/26d30fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110270000/110263700/110263621/a6b3259b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/111000000/110270000/110263700/110263621/dfcebd13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Warren

[](https://www.expedia.ca/Warren-Hotels-Top-Of-The-Hill-Modern-Retreat.h110263621.Hotel-Information)

9.8/10

Exceptional

(6 reviews)

"Really nice place everything was top notch. "

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

Michael Q.

CA $238

CA $892 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Warren-Hotels-Top-Of-The-Hill-Modern-Retreat.h110263621.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/19bccfea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/8634aa3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/1083183d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/e502214a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Killington

[](https://www.expedia.ca/Killington-Hotels-Cozy-2BR-Mountain-Retreat-Near-Killington-Resort-Pet-Friendly-W-Fireplace.h120652390.Hotel-Information)

CA $240

CA $675 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Killington-Hotels-Cozy-2BR-Mountain-Retreat-Near-Killington-Resort-Pet-Friendly-W-Fireplace.h120652390.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/c3df7e46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/f1219ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/9f5da7f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/1b212a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bridgewater

[](https://www.expedia.ca/Bridgewater-Hotels-Bridgewater-Inn-2-King-Beds-Game-Room-Skiing.h90692944.Hotel-Information)

9.6/10

Exceptional

(7 reviews)

"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."

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

Owen C.

CA $358

CA $877 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Bridgewater-Hotels-Bridgewater-Inn-2-King-Beds-Game-Room-Skiing.h90692944.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)

![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)

![Hair dryer, towels](https://images.trvl-media.com/lodging/49000000/48670000/48666200/48666141/e6a64143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Woodstock

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

10/10

Exceptional

(30 reviews)

"Beautiful home. It was a good location for my family to attend a family wedding at the Woodstock Inn."

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

Robin H.

CA $1,255

CA $2,038 total

includes taxes & fees

Jan 20 - Jan 21

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

![Dining](https://images.trvl-media.com/lodging/123000000/122620000/122614400/122614350/a5d5b008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/123000000/122620000/122614400/122614350/5d8432b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/123000000/122620000/122614400/122614350/b1520960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122620000/122614400/122614350/93a3db2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Mendon

[](https://www.expedia.ca/Rutland-Hotels-Large-Ski-Ranch-Hot-Tub-Close-To-Killington-Pets-Ok.h122614350.Hotel-Information)

10/10

Exceptional

(1 review)

"Amazing stay! Gorgeous house, clean, perfect location. The host was super responsive and made the check in check out process so easy.Highly reccomend and can’t wait to stay again next year. "

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

Nicole H.

CA $481

CA $962 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Rutland-Hotels-Large-Ski-Ranch-Hot-Tub-Close-To-Killington-Pets-Ok.h122614350.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304254/31553740.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304254/37701d82.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/120000000/119310000/119304300/119304254/eede2581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304254/f03ca5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Rutland

[](https://www.expedia.ca/Rutland-Hotels-Spacious-Central-4BR.h119304254.Hotel-Information)

10/10

Exceptional

(1 review)

CA $294

CA $641 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Rutland-Hotels-Spacious-Central-4BR.h119304254.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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Apartments

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Condos

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Cottages

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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=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=CHALET)

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## Top Pittsfield Hotel Reviews

![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

"Check in service Breakfast"

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

"Was great"

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

![Greenbrier Inn](https://images.trvl-media.com/lodging/2000000/1180000/1176800/1176792/e5569f51_y.jpg)

### Greenbrier Inn

10/10 Excellent

"Very friendly and helpful staff"

[](https://expedia.ca/Killington-Hotels-Greenbrier-Inn.h1176792.Hotel-Information)

![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg)

### The Shire Woodstock

10/10 Excellent

"Beautiful area. The ground floor room was perfect!"

[](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.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

"Solid accommodations. "

[](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.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. Rooms were very clean, staff was kind, nice and quiet. Full sized fridge in the room. Only 3 floors which was nice because I cant take elevators. I travel to this area about 8 times a year and will definitely stay here again."

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

"Very easy to get to, very clean and spacious room and excellent staff attention"

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

![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg)

### Mountain Sports Inn

10/10 Excellent

"Great spot, great people couldn’t ask for more, would 10/10 recommend "

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

![Summit Lodge](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/5da3617c_y.jpg)

### Summit Lodge

10/10 Excellent

"Breakfast was great!"

[](https://expedia.ca/Killington-Hotels-Summit-Lodge.h1102506.Hotel-Information)

## Find out more about Pittsfield

## Pittsfield Vacation Homes information

| Number of reviews | 178                |
| ----------------- | ------------------ |
| Accommodation     | 559 Vacation Homes |
| Lowest Price      | CA $130            |
| Highest Price     | CA $2,038          |

## Explore a world of travel with Expedia

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- [Hotels near Pico Mountain at Killington Ski Resort ](https://www.expedia.ca/Pico-Mountain-At-Killington-Ski-Resort-Hotels.0-l6082891-0.Travel-Guide-Filter-Hotels)
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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)
- [Green Mountain National Golf Course ](https://www.expedia.ca/Green-Mountain-National-Golf-Course-Killington.d6115884.Vacation-Attraction)
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- [Pico Mountain at Killington Ski Resort ](https://www.expedia.ca/Pico-Mountain-At-Killington-Ski-Resort-Killington.d6082891.Vacation-Attraction)

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- [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)