Title: Pittsfield Vacation Rentals from CA $258: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two 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 three 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)

In four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-06-05&endDate=2026-06-07&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 rentals

![TV](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/db902092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/e8d5db6a.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)

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

### Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

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

North Sherburne

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.

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

![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)

![Exterior](https://images.trvl-media.com/lodging/124000000/123490000/123480200/123480177/586cbc8b.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)

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

### NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

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

North Sherburne

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

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114400000/114397800/114397721/545a394c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114400000/114397800/114397721/c63de027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114400000/114397800/114397721/cb3fb1ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114400000/114397800/114397721/66a92d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Glamping hut with WiFi in Ripton, biking, hiking, skiing

[](https://www.expedia.ca/Ripton-Hotels-Glamping-Hut-With-WiFi-In-Ripton.h114397721.Hotel-Information)

Ripton

10/10

Exceptional

(3 reviews)

"Super cute and cozy! It was perfect."

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

Sarah D.

CA $121

CA $226 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Ripton-Hotels-Glamping-Hut-With-WiFi-In-Ripton.h114397721.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119700000/119697100/119697097/eb74448a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119700000/119697100/119697097/14d6532f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119700000/119697100/119697097/e304b592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/120000000/119700000/119697100/119697097/4b80a474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

[](https://www.expedia.ca/South-Royalton-Hotels-Escape-To-This-Private-And-Peaceful-Tiny-Home-With-Hot-Tub-In-Sharon.h119697097.Hotel-Information)

Sharon

10/10

Exceptional

(7 reviews)

"Cabin was spotless and exactly what I expected"

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

mark g.

CA $190

CA $412 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/South-Royalton-Hotels-Escape-To-This-Private-And-Peaceful-Tiny-Home-With-Hot-Tub-In-Sharon.h119697097.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74590000/74583300/74583296/e01579e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/75000000/74590000/74583300/74583296/80d45758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74590000/74583300/74583296/af166be4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74590000/74583300/74583296/060c4f48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded retreat in the trees

[](https://www.expedia.ca/Randolph-Hotels-Sunny.h74583296.Hotel-Information)

Roxbury

10/10

Exceptional

(40 reviews)

"Perfect, quiet location and the host were very responsive! Me and my daughter stayed for a girls getaway for a hiking trip and the location was perfect for the weekend activities. Look forward to staying here in the future. "

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

Erin M.

CA $182

CA $342 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Randolph-Hotels-Sunny.h74583296.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90120000/90115100/90115091/13076901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90120000/90115100/90115091/ebe22124.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90120000/90115100/90115091/cf3838ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90120000/90115100/90115091/7ddaf7ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vermont Suite | 10 Min to Killington & Woodstock

[](https://www.expedia.ca/Bridgewater-Hotels-NEW-Ben-Jerrys-Suite-At-The-Bridgewater-Inn.h90115091.Hotel-Information)

Bridgewater

9.2/10

Wonderful

(7 reviews)

"Overall, a great stay. "

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

Meghan J.

CA $129

CA $287 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Bridgewater-Hotels-NEW-Ben-Jerrys-Suite-At-The-Bridgewater-Inn.h90115091.Hotel-Information)

![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)

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

![Interior](https://images.trvl-media.com/lodging/74000000/73730000/73729100/73729008/c116411c.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

(34 reviews)

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

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

Jill F.

CA $160

CA $289 total

includes taxes & fees

Feb 18 - Feb 19

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

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82970000/82961200/82961114/29a332c9.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)

![Books](https://images.trvl-media.com/lodging/83000000/82970000/82961200/82961114/0d2faf4b.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

(72 reviews)

"Great place to stay for a Vermont getaway! "

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

Jeremy H.

CA $163

CA $258 total

includes taxes & fees

Feb 13 - Feb 14

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

![Interior](https://images.trvl-media.com/lodging/108000000/107910000/107909000/107908933/0c26463f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/108000000/107910000/107909000/107908933/d79ef6b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107910000/107909000/107908933/49463cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107910000/107909000/107908933/1730b6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

[](https://www.expedia.ca/Rutland-Hotels-The-Mendon-Cottage-Charming-Home-Close-To-Killington-Discounted-Lift-Tickets.h107908933.Hotel-Information)

Mendon

9.8/10

Exceptional

(11 reviews)

"Great place! Secluded but close to everything. We will definitely stay again."

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

Patricia Y.

CA $339

CA $794 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Rutland-Hotels-The-Mendon-Cottage-Charming-Home-Close-To-Killington-Discounted-Lift-Tickets.h107908933.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/111000000/110410000/110405300/110405218/63aefb02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110410000/110405300/110405218/890ec039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/111000000/110410000/110405300/110405218/5b113397.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/111000000/110410000/110405300/110405218/a0ab4d38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

[](https://www.expedia.ca/Killington-Hotels-Picos-Doorstep-Ski-OnOff.h110405218.Hotel-Information)

Killington

9.8/10

Exceptional

(10 reviews)

"perfect setup, very clean and comfortable. "

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

Jeremiah J.

[](https://www.expedia.ca/Killington-Hotels-Picos-Doorstep-Ski-OnOff.h110405218.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)

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

![Interior](https://images.trvl-media.com/lodging/101000000/100340000/100335500/100335420/9d0ca37f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

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

Mendon

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 $175

CA $381 total

includes taxes & fees

Mar 2 - Mar 3

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101910000/101900700/101900661/b1cd5c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101910000/101900700/101900661/4e57eb17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101910000/101900700/101900661/9c48ff3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101910000/101900700/101900661/58db806d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jack S\`Bearo - Slopes, Fireplace, Pool.

[](https://www.expedia.ca/Killington-Hotels-Jack-SBearo-Slopeside-At-Pico-Shuttle-To-Killy.h101900661.Hotel-Information)

Killington

10/10

Exceptional

(14 reviews)

"My husband and i really enjoyed our stay at Jack S'bearo! Was a nice, cozy condo for a couple or a small family. Highly recommend!"

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

Erin

CA $145

CA $415 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Killington-Hotels-Jack-SBearo-Slopeside-At-Pico-Shuttle-To-Killy.h101900661.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120810000/120807700/120807632/ba38021b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/121000000/120810000/120807700/120807632/203b44f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120810000/120807700/120807632/fc7a6330.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/121000000/120810000/120807700/120807632/dcc8c078.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Rustic Cabin, NOTE: pipes are frozen. Please don’t book now! Back soon.

[](https://www.expedia.ca/Rutland-Hotels-Cozy-Cabin.h120807632.Hotel-Information)

Rutland

9.6/10

Exceptional

(9 reviews)

CA $215

CA $275 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Rutland-Hotels-Cozy-Cabin.h120807632.Hotel-Information)

![Fireplace, books](https://images.trvl-media.com/lodging/34000000/33150000/33141400/33141363/190c0a51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books](https://images.trvl-media.com/lodging/34000000/33150000/33141400/33141363/600fda3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33150000/33141400/33141363/4d1fbd50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33150000/33141400/33141363/e39b8080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stetson Hollow Cabin by Stetson Brook

[](https://www.expedia.ca/Warren-Hotels-Stetson-Hollow-Cabin-By-Stetson-Brook.h33141363.Hotel-Information)

Warren

9.8/10

Exceptional

(162 reviews)

"The cabin location was ideal for us , very convenient to outings and very cozy in a gorgeous setting . "

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

judy c.

CA $293

CA $601 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Warren-Hotels-Stetson-Hollow-Cabin-By-Stetson-Brook.h33141363.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/120000000/119870000/119869800/119869798/c7907ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119870000/119869800/119869798/6a4b87c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119870000/119869800/119869798/84cc0b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119870000/119869800/119869798/1227d611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Rutland Retreat

[](https://www.expedia.ca/Rutland-Hotels-Cozy-Rutland-Retreat.h119869798.Hotel-Information)

Rutland

9.6/10

Exceptional

(5 reviews)

"Peaceful stay in the city! We were headed to the rodeo, so this was the perfect distance away! "

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

Aislinn F.

CA $138

CA $299 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Rutland-Hotels-Cozy-Rutland-Retreat.h119869798.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/91000000/90150000/90149600/90149596/fdcdea3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books](https://images.trvl-media.com/lodging/91000000/90150000/90149600/90149596/0431a8e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books](https://images.trvl-media.com/lodging/91000000/90150000/90149600/90149596/db61bc77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90150000/90149600/90149596/72975903.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

[](https://www.expedia.ca/Killington-Hotels-5th-Floor-Mountain-View-Condo.h90149596.Hotel-Information)

Killington

9.2/10

Wonderful

(13 reviews)

"Great property, as advertised."

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

Chris A.

CA $185

CA $446 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Killington-Hotels-5th-Floor-Mountain-View-Condo.h90149596.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/83000000/82950000/82946500/82946425/d907f555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/83000000/82950000/82946500/82946425/cfa1484c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/83000000/82950000/82946500/82946425/81f9f98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/83000000/82950000/82946500/82946425/50891cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfortable mountain gem with pool, mountain views, & indoor parking space

[](https://www.expedia.ca/Killington-Hotels-Comfortable-Mountain-Gem-With-Fast-Wifi.h82946425.Hotel-Information)

Killington

8.4/10

Very good

(35 reviews)

"Great stay!"

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

Bryann F.

CA $136

CA $450 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Killington-Hotels-Comfortable-Mountain-Gem-With-Fast-Wifi.h82946425.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/33000000/32140000/32139200/32139178/f0d8549c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/33000000/32140000/32139200/32139178/e2065bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/33000000/32140000/32139200/32139178/a125b83c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32140000/32139200/32139178/ae5ff31a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Clean & bright condo with mountain views & modern kitchen - walk to lifts

[](https://www.expedia.ca/Killington-Hotels-Clean-Bright-Condo-With-Mountain-Views-Modern-Kitchen-Walk-To-Lifts.h32139178.Hotel-Information)

Killington

7.2/10

Good

(45 reviews)

"Perfect place for a long weekend"

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

Patrick D.

CA $114

CA $369 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Killington-Hotels-Clean-Bright-Condo-With-Mountain-Views-Modern-Kitchen-Walk-To-Lifts.h32139178.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/48be0320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/c33b35a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/efdfd8b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/98a04e79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gnome Home Mountain Ski Chalet w/Sauna Killington

[](https://www.expedia.ca/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information)

Stockbridge

10/10

Exceptional

(4 reviews)

"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"

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

Gerald S.

CA $373

CA $782 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/101000000/101000000/100996900/100996829/2925807e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/101000000/101000000/100996900/100996829/dca1ec05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/101000000/101000000/100996900/100996829/514eb474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 3 Bedrooms | View from room](https://images.trvl-media.com/lodging/101000000/101000000/100996900/100996829/cf0bfccb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Green

[](https://www.expedia.ca/Killington-Hotels-Mountain-Green.h100996829.Hotel-Information)

Killington

7.2/10

Good

(20 reviews)

"Great !"

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

Raul

CA $280

CA $376 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Killington-Hotels-Mountain-Green.h100996829.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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Cottages

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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=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&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=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&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=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=VILLA)

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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

"Room was excellent! Very clean and very comfortable. Bed and comforter were fantastic. Beautiful view in the back . The whole hotel is so nicely dec with antics all around. Have stayed few before will continue to come back. Sent my daughter here as well As a little gift. "

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

"People went out of their way to help My wife needed distilled water for her C-Pap machine the staff went out to store so she could have some. Restaurant was great Room was clean "

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

"Clean room, friendly stas"

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

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

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

### Brandon Inn

10/10 Excellent

"My family stayed (6 of us) at the Brandon Inn this weekend (2/6-8) to go skiing at Pico and snowshoeing. What a wonderful Inn with old time charm. 200+ year old Inn has an inviting air about it as you learn about its history and evolution as an Inn since the 1700s. Friday and Saturday we were entertained by Ana Guigui, a piano player, who interacts with the audience for her playlist and makes each night feel new and fresh. Amazing and the Innkeeper could not be more accommodating to your needs. Really can’t wait until I can go back and stay there again. Highly recommend. "

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

"Staff was very attentive and helpful, rooms very clean and comfortable with well organized setting, breakfast was pretty good and it is included with your stay."

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

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

### The Shire Woodstock

10/10 Excellent

"Great room, lovely view and a wonderful town "

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

"Staff was helpful and room was clean"

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

"Everything was great! The staff were very nice and the free breakfast is legit!"

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

## Find out more about Pittsfield

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pittsfield. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Condo Rentals in Pittsfield ](https://expedia.ca/Pittsfield-Condos.d184066-aaCondos.Travel-Guide-Accommodation)
- [Vacation Homes in Pittsfield ](https://expedia.ca/Pittsfield-Private-Vacation-Homes.d184066-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Pittsfield ](https://expedia.ca/Pittsfield-Apartments.d184066-aaApartments.Travel-Guide-Accommodation)
- [Cabin Rentals in Pittsfield ](https://expedia.ca/Pittsfield-Cabins.d184066-aaCabins.Travel-Guide-Accommodation)
- [Cottages in Pittsfield ](https://expedia.ca/Pittsfield-Cottages.d184066-aaCottages.Travel-Guide-Accommodation)
- [Chalets in Pittsfield ](https://expedia.ca/Pittsfield-Chalets.d184066-aaChalets.Travel-Guide-Accommodation)
- [Lodges in Pittsfield ](https://expedia.ca/Pittsfield-Lodges.d184066-aaLodges.Travel-Guide-Accommodation)
- [B&B in Pittsfield ](https://expedia.ca/Pittsfield-Bed-And-Breakfast.d184066-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Farmstay in Pittsfield ](https://expedia.ca/Pittsfield-Agritourism.d184066-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Pittsfield ](https://expedia.ca/Pittsfield-Motels.d184066-aaMotels.Travel-Guide-Accommodation)
- [Inns in Pittsfield ](https://expedia.ca/Pittsfield-Inns.d184066-aaInns.Travel-Guide-Accommodation)
- [Guest Houses in Pittsfield ](https://expedia.ca/Pittsfield-Guest-Houses.d184066-aaGuestHouses.Travel-Guide-Accommodation)
- [Villas in Pittsfield ](https://expedia.ca/Pittsfield-Villas.d184066-aaVillas.Travel-Guide-Accommodation)
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- [Treehouses in Pittsfield ](https://expedia.ca/Pittsfield-Treehouses.d184066-aaTreehouses.Travel-Guide-Accommodation)
- [Condo Resorts in Pittsfield ](https://expedia.ca/Pittsfield-Condominium-Resort.d184066-aaCondominiumResort.Travel-Guide-Accommodation)

## Frequently asked questions

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