Title: The Best Pittsfield, VT Chalets from $461 | Expedia.com

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

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.com/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 two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Pittsfield chalets

![Exterior](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/d42e6390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/1a5b9e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/a11e6e92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/7e228bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in East Warren

[](https://www.expedia.com/Warren-Hotels-Dreamy-Artist-Chalet-In-Secluded-Historic-Village.h63026865.Hotel-Information)

9.6/10

Exceptional

(14 reviews)

"Everything was beautiful. But for sure needs new mattress and pillows. "

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

Jeanette R.

$412 nightly

$461 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Warren-Hotels-Dreamy-Artist-Chalet-In-Secluded-Historic-Village.h63026865.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)

![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)

![TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/b2a8b57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Stockbridge

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

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.

$506 nightly

$535 total

Mar 24 - Mar 25

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/102000000/101010000/101007200/101007141/8a8dfe15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101010000/101007200/101007141/086d7028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101010000/101007200/101007141/962e1595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101010000/101007200/101007141/e67cd3ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in East Warren

[](https://www.expedia.com/Warren-Hotels-Authentic-Log-Home-In-Warren-Ski-Town-Mountain-Biking-Short-Walk-To-Lake.h101007141.Hotel-Information)

10/10

Exceptional

(3 reviews)

"The house is amazing. The hosts clearly love it, and it shows in how well it is set up and stocked. Highly recommended."

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

Greg E.

$596 nightly

$668 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Warren-Hotels-Authentic-Log-Home-In-Warren-Ski-Town-Mountain-Biking-Short-Walk-To-Lake.h101007141.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/e9ee5480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/45bdedf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/8cd00c8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/fa430ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in North Sherburne

[](https://www.expedia.com/Killington-Hotels-Fabulous-4-Bedroom-Chalet-In-Tranquil-Killington-Getaway-With-Gorgeous-Hot-Tub.h123266945.Hotel-Information)

7.6/10

Good

(9 reviews)

$533 nightly

$602 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Killington-Hotels-Fabulous-4-Bedroom-Chalet-In-Tranquil-Killington-Getaway-With-Gorgeous-Hot-Tub.h123266945.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/97000000/96030000/96029800/96029719/6b02a563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dishwasher, electric kettle, spices, dining tables](https://images.trvl-media.com/lodging/97000000/96030000/96029800/96029719/31ea8443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, foosball](https://images.trvl-media.com/lodging/97000000/96030000/96029800/96029719/b2f6042d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/97000000/96030000/96029800/96029719/8e8c7e4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Killington

[](https://www.expedia.com/Killington-Hotels-The-Overlook-Hot-Tub.h96029719.Hotel-Information)

10/10

Exceptional

(2 reviews)

"We stayed at the overlook for a family ski trip. It was the perfect place for our family of 4 with 2 young kids. The house was well appointed and what we expected, our hosts communicated well and it was an easy drive to killington mountain every day to ski."

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

Matt F.

$836 nightly

$945 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Killington-Hotels-The-Overlook-Hot-Tub.h96029719.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/400cdd0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/1a4e96ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/ecac89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/a250ff08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Killington

[](https://www.expedia.com/Killington-Hotels-BearHaus-New-Reno.h89982066.Hotel-Information)

9.6/10

Exceptional

(5 reviews)

"Great property - excellent hosts. Close to mountain and restaurants"

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

Eric D.

$1,127 nightly

$1,274 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Killington-Hotels-BearHaus-New-Reno.h89982066.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/81000000/80820000/80813400/80813386/8d12bb48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/81000000/80820000/80813400/80813386/7f709f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/81000000/80820000/80813400/80813386/2c0a2719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/81000000/80820000/80813400/80813386/aaabeade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Killington

[](https://www.expedia.com/Killington-Hotels-Kilbourne-LodgeMid-Century-Chalet-Killington-RdPet-Family-Friendly.h80813386.Hotel-Information)

9.4/10

Exceptional

(8 reviews)

"Great stay, thanks!"

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

Bret R.

$1,281 nightly

$1,447 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Killington-Hotels-Kilbourne-LodgeMid-Century-Chalet-Killington-RdPet-Family-Friendly.h80813386.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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Condos

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Cottages

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Apartments

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Chalets

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Villas

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## Top Pittsfield Hotel Reviews

![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

"Very friendly staff!!! "

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

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

### Best Western Inn & Suites Rutland-Killington

10/10 Excellent

"Our stay was delightful, with fresh cookies at check-in, friendly staff, spacious room and amenities, the grounds are well kept and operated with a family owned feel. Killington is 20 min away by major road. Great stay! "

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

![Hampton Inn Rutland](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/f4f05fc2_y.jpg)

### Hampton Inn Rutland

10/10 Excellent

"The front desk staff was very helpful. "

[](https://expedia.com/Rutland-Hotels-Hampton-Inn-Rutland.h1522922.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

"Location and amenities and friendly staff."

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

![The Mountain Top Inn & Resort](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/53dd6cd4_y.jpg)

### The Mountain Top Inn & Resort

10/10 Excellent

"Love this gem of a place! Cozy, great food and yummy cocktails. Exceeded our expectations and the waitstaff was phenomenal-shout out to Brendan the bartender he was awesome Sledding, horse ride in a carriage, skating hot tub and so much more! "

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

![Cozy Loft for two with Hot Tub & Mtn Views](https://images.trvl-media.com/lodging/60000000/59790000/59784500/59784421/434c8b92_y.jpg)

### Cozy Loft for two with Hot Tub & Mtn Views

10/10 Excellent

"This sweet little spot was just perfect for our winter stay. Jeff was very present and available throughout our stay for any questions. We appreciated the snowshoe trails within walking distance from the location. The hot tub was an absolute bonus! I love the intimacy of the size of the tiny house and all the Wood brought me such joy."

[](https://expedia.com/Granville-Hotels-Romantic-Loft-With-Hot-Tub.h59784421.Hotel-Information)

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

### Summit Lodge

10/10 Excellent

"It’s a great lodge. This place has a lot of character. So beautiful inside and out. Rooms are very clean. Updated bathrooms. Hot tub was amazing especially after all day skiing. Bar and bar staff was awesome. Very helpful. Breakfast was one of the best tasted open buffets. Sausage and bacon were the best. I highly recommend this place. We definitely come again ! "

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

![Emrose Luxury Cabins](https://images.trvl-media.com/lodging/111000000/110250000/110247200/110247154/fb359a4e_y.jpg)

### Emrose Luxury Cabins

10/10 Excellent

"We had such an amazing stay at these cabins—truly the perfect start to an unforgettable weekend. We were in town for a ski trip, and with our friend planning to propose, this cabin was the ideal setting to set the mood the night before. The atmosphere was cozy, romantic, and exactly what we hoped for. Each cabin has its own special feel and unique architecture, which made the experience even more memorable and charming. The cabins are conveniently located, and we loved that there are hot tubs spread throughout the property. The hosts were incredibly responsive and helpful from start to finish, especially with food recommendations. When we let them know we were on our way, they even had the hot tub heating up and ready for us upon arrival, which was such a thoughtful touch. I also reached out ahead of time to ask if two cabins next to each other could be accommodated, and they were beyond helpful and made the process so easy. You can really tell they care about their guests’ experience. Helpful tips for future guests: bring slippers to wear inside the cabins since no shoes are allowed, and definitely bring a robe for the walk to the hot tub—it makes the experience even better! We couldn’t have asked for a better stay and would absolutely recommend these cabins to anyone looking for a relaxing, memorable getaway. ⭐️⭐️⭐️⭐️⭐️"

[](https://expedia.com/Brandon-Hotels-Emrose-Luxury-Cabins.h110247154.Hotel-Information)

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

### Woodstock Inn & Resort

10/10 Excellent

"Very clean, high end, friendly staff "

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

## Find out more about Pittsfield

## Pittsfield Chalets information

| Number of reviews | 36         |
| ----------------- | ---------- |
| Accommodation     | 33 Chalets |
| Lowest Price      | $461       |
| Highest Price     | $1,447     |

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- [Flights to Gaysville ](https://www.expedia.com/Cheap-Flights-To-Gaysville.d3000749241.Travel-Guide-Flights)
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- [Visit Stockbridge ](https://www.expedia.com/Stockbridge.dx6357893)
- [Stockbridge Vacations ](https://www.expedia.com/Stockbridge.d6357893.Destination-Travel-Guides)
- [Visit Gaysville ](https://www.expedia.com/Gaysville.dx3000749241)
- [Appalachian Trail Adventures ](https://www.expedia.com/Appalachian-Trail-Adventures-Rutland.d553248621532667612.Vacation-Attraction)
- [Green Mountain National Golf Course ](https://www.expedia.com/Green-Mountain-National-Golf-Course-Killington.d6115884.Vacation-Attraction)
- [Lefferts Pond ](https://www.expedia.com/Lefferts-Pond-Chittenden.d6291323.Vacation-Attraction)
- [Visit Killington ](https://www.expedia.com/Killington.dx10780)
- [Killington Vacations ](https://www.expedia.com/Killington.d10780.Destination-Travel-Guides)

- [Car rentals near Stockbridge ](https://www.expedia.com/Car-Rentals-In-Stockbridge.d6357893.Car-Rental-Guide)
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- [Killington Vacation Rentals ](https://www.expedia.com/Killington-Vacation-Rentals.d10780.Travel-Guide-VacationRentals)