Title: Pittsfield Vacation Rentals from $233: Search Short-Term Rentals | Expedia.com

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## Check prices for these dates

In two weeks

[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 two months

[Jun 5 - Jun 7](https://www.expedia.com/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)

In three months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 31 - Aug 2](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-07-31&endDate=2026-08-02&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

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123490000/123480200/123480177/00bd424c.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)

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

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

North Sherburne

$532 nightly

$596 total

Apr 13 - Apr 14

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/17000000/16350000/16341300/16341282/bf24c523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin 5 (Pet Friendly) - Owl's Branch | Living area | Flat-screen TV, fireplace, DVD player](https://images.trvl-media.com/lodging/17000000/16350000/16341300/16341282/87344fcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/17000000/16350000/16341300/16341282/27dce88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/17000000/16350000/16341300/16341282/b2bb8d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Robert Frost Mountain Cabins

[](https://www.expedia.com/Ripton-Hotels-Robert-Frost-Mountain-Cabins.h16341282.Hotel-Information)

Ripton

10/10

Exceptional

(40 reviews)

"Ammazing,would go again!"

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

Joseph

$257 nightly

$280 total

May 5 - May 6

Total with taxes and fees

[](https://www.expedia.com/Ripton-Hotels-Robert-Frost-Mountain-Cabins.h16341282.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)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33150000/33141400/33141363/82acf25c.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)

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

### Stetson Hollow Cabin by Stetson Brook

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

Warren

9.8/10

Exceptional

(167 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.

$390 nightly

$437 total

Apr 8 - Apr 9

Total with taxes and fees

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

![Dining](https://images.trvl-media.com/lodging/75000000/74590000/74583300/74583296/0fc5fcaa.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.com/Randolph-Hotels-Secluded-Retreat-In-The-Trees.h74583296.Hotel-Information)

Roxbury

10/10

Exceptional

(41 reviews)

"We had a great time staying in this house. For our family, it was comfortable, clean and bright and had everything we needed. "

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

David R.

$218 nightly

$244 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Randolph-Hotels-Secluded-Retreat-In-The-Trees.h74583296.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/122000000/121200000/121193900/121193871/e7707ef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 1 Bedroom | Private kitchen | Mini-fridge, microwave, oven, cookware/dishes/utensils](https://images.trvl-media.com/lodging/122000000/121200000/121193900/121193871/9c65fc7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | View from room](https://images.trvl-media.com/lodging/122000000/121200000/121193900/121193871/7b94eb88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 1 Bedroom | Living area | 45-inch Smart TV with cable channels](https://images.trvl-media.com/lodging/122000000/121200000/121193900/121193871/1e625bb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Suites at Killington Center

[](https://www.expedia.com/Killington-Hotels-The-Suites-At-Killington-Center.h121193871.Hotel-Information)

Killington

$331 nightly

$364 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Killington-Hotels-The-Suites-At-Killington-Center.h121193871.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)

![Exterior detail](https://images.trvl-media.com/lodging/120000000/119700000/119697100/119697097/4b80a474.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119700000/119697100/119697097/6ddc77d5.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.com/South-Royalton-Hotels-Escape-To-This-Private-And-Peaceful-Tiny-Home-With-Hot-Tub-In-Sharon.h119697097.Hotel-Information)

Sharon

10/10

Exceptional

(8 reviews)

"The accommodations were very lovely. The host was friendly."

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

Serge

$260 nightly

$291 total

Apr 12 - Apr 13

Total with taxes and fees

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

![Dining](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663196/11223970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663196/c3fec788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663196/960544ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663196/24c58400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool

[](https://www.expedia.com/Killington-Hotels-Ski-InSki-Out-Sunrise-Village-Condo-2BR.h120663196.Hotel-Information)

Killington

10/10

Exceptional

(36 reviews)

"Ski in ski out when the sun lift is operational."

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

Vinayak G.

$730 nightly

$825 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Killington-Hotels-Ski-InSki-Out-Sunrise-Village-Condo-2BR.h120663196.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559434/6a529202.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/112000000/111560000/111559500/111559434/a4f4882e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559434/a073bac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559434/4ab54715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna. Ski Deals Too.

[](https://www.expedia.com/Killington-Hotels-Trailside-Village-6-Slopeside-3BR2BA-Hot-Tub-Sauna-Ski-InOut-With-Discounted-Lift-Tickets.h111559434.Hotel-Information)

Killington

9.6/10

Exceptional

(72 reviews)

"Amazing ski-in/out property slope-side! We enjoyed our stay very much! "

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

Jason

$950 nightly

$1,074 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Killington-Hotels-Trailside-Village-6-Slopeside-3BR2BA-Hot-Tub-Sauna-Ski-InOut-With-Discounted-Lift-Tickets.h111559434.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)

![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)

![Indoor pool](https://images.trvl-media.com/lodging/101000000/101000000/100996900/100996829/a2bbfdb4.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)

### Mountain Green

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

Killington

7.2/10

Good

(23 reviews)

"I enjoy the location "

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

troy

$212 nightly

$233 total

Apr 13 - Apr 14

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111610000/111604000/111603993/809aa654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111610000/111604000/111603993/dbb83699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111610000/111604000/111603993/d0a56570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111610000/111604000/111603993/ff98197f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

[](https://www.expedia.com/Killington-Hotels-The-Navillus-House-Hot-Tub.h111603993.Hotel-Information)

Killington

10/10

Exceptional

(63 reviews)

"Great stay, everything was clean and location was amazing."

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

John D.

$986 nightly

$1,114 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Killington-Hotels-The-Navillus-House-Hot-Tub.h111603993.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)

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107910000/107909000/107908933/f4223681.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)

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

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

Mendon

9.8/10

Exceptional

(14 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.

$378 nightly

$423 total

Apr 8 - Apr 9

Total with taxes and fees

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

![TV](https://images.trvl-media.com/lodging/73000000/72140000/72131700/72131664/a283578c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131700/72131664/1dab8185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/73000000/72140000/72131700/72131664/5c70d1ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72140000/72131700/72131664/dae29296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

[](https://www.expedia.com/Plymouth-Hotels-Hawk-Mountain-Retreat-Near-Okemo-With-Fireplace.h72131664.Hotel-Information)

Plymouth

9.8/10

Exceptional

(24 reviews)

"The Nest at Hawk Ledges was a perfect summer getaway. The home provides comfort in a tranquil setting while being close enough to many summer adventures. We enjoyed relaxing in the bright, open home after taking many day trips to explore the area. What a gem!"

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

Ben N.

$621 nightly

$696 total

Apr 16 - Apr 17

Total with taxes and fees

[](https://www.expedia.com/Plymouth-Hotels-Hawk-Mountain-Retreat-Near-Okemo-With-Fireplace.h72131664.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/36000000/35700000/35697600/35697555/8e768b98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/36000000/35700000/35697600/35697555/5cf06203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/36000000/35700000/35697600/35697555/a8e21c1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/36000000/35700000/35697600/35697555/db71194d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Adorable cabin with screened porch and private fire pit

[](https://www.expedia.com/Ripton-Hotels-Adorable-Cabin-With-Screened-Porch-And-Private-Fire-Pit.h35697555.Hotel-Information)

Ripton

10/10

Exceptional

(5 reviews)

"Wonderful place to stay tucked away in the woods. The owners are extremely thoughtful and personable. Can’t wait to go back. "

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

Sorin

$317 nightly

$347 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Ripton-Hotels-Adorable-Cabin-With-Screened-Porch-And-Private-Fire-Pit.h35697555.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100490000/100486600/100486523/0fed62a2.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)

![Smart TV, offices](https://images.trvl-media.com/lodging/101000000/100490000/100486600/100486523/92485027.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)

### BruinsDen- Fooseball, Hot Tub, Mountain Views

[](https://www.expedia.com/Killington-Hotels-BruinsDen-Ski-On-Ski-Off.h100486523.Hotel-Information)

Killington

9.8/10

Exceptional

(19 reviews)

"We loved our stay, felt like home away from home. A perfect place to relax after a day on the slopes. Grateful for our time there. #recommend!"

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

Jennifer C.

$926 nightly

$1,020 total

Apr 19 - Apr 20

Total with taxes and fees

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

![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)

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

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

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

Leicester

10/10

Exceptional

(73 reviews)

"Great place to stay for a Vermont getaway! "

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

Jeremy H.

$160 nightly

$179 total

Apr 8 - Apr 9

Total with taxes and fees

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

![Smart TV, fireplace](https://images.trvl-media.com/lodging/117000000/116140000/116132500/116132444/6ad0f1f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116140000/116132500/116132444/184189f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116140000/116132500/116132444/35bc8369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/117000000/116140000/116132500/116132444/f93cb489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Matterhorn House: Killington Chalet w/ Hot Tub, Views, Game Room - Ideal Spring to Fall

[](https://www.expedia.com/Killington-Hotels-The-Matterhorn-House-Killington-Chalet-W-Hot-Tub.h116132444.Hotel-Information)

Killington

9.2/10

Wonderful

(48 reviews)

"One of the best vrbo to date thank you!!!"

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

jim c.

$1,042 nightly

$1,177 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Killington-Hotels-The-Matterhorn-House-Killington-Chalet-W-Hot-Tub.h116132444.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/68000000/67460000/67451000/67450962/f8344afd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/68000000/67460000/67451000/67450962/a0ebf57c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/68000000/67460000/67451000/67450962/535453e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67460000/67451000/67450962/78a75a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SunBear-Ski on Ski off, Pool, HotTub, Game Room!

[](https://www.expedia.com/Killington-Hotels-SunBear-Pool.h67450962.Hotel-Information)

Killington

10/10

Exceptional

(29 reviews)

"Clean and perfect"

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

Cyle D.

$503 nightly

$569 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Killington-Hotels-SunBear-Pool.h67450962.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/87d01392.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)

![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/64000000/63030000/63026900/63026865/7e228bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dreamy Artist Chalet in Secluded Historic Village

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

East Warren

9.6/10

Exceptional

(16 reviews)

"Receptive. Clean. If coming in winter/ mud, know that there is zero chance you'll make it unless you have real chains or 4wd. Nice place. "

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

Jessica S.

$365 nightly

$409 total

Apr 8 - Apr 9

Total with taxes and fees

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

![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)

![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.com/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.

$205 nightly

$230 total

Apr 9 - Apr 10

Total with taxes and fees

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

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/40000000/40000000/39991500/39991401/61181c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/40000000/39991500/39991401/67b64f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/40000000/40000000/39991500/39991401/e3b78985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/40000000/40000000/39991500/39991401/2e2b7f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

[](https://www.expedia.com/Ripton-Hotels-Charming-And-Meticulously-Cleaned-Cabin-With-Panoramic-View-Of-The-Green-Mtns.h39991401.Hotel-Information)

Ripton

10/10

Exceptional

(17 reviews)

"Beautiful place. Lots to do around the cabin and in the area. The hosts are very helpful. The cabin has everything you could want for a great stay. "

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

Susan

$317 nightly

$347 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Ripton-Hotels-Charming-And-Meticulously-Cleaned-Cabin-With-Panoramic-View-Of-The-Green-Mtns.h39991401.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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-21&endDate=2026-04-22&regionId=184066&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

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Cottages

[](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America&regionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=COTTAGE)

Private vacation homes

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Apartments

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Condos

[](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America&regionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CONDO)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America&regionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VILLA)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America&regionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CHALET)

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## Top Pittsfield Hotel Reviews

![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

"Front desk was helpful and pleasant"

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

![Comfort Inn Rutland - Killington](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/b2987a71_y.jpg)

### Comfort Inn Rutland - Killington

10/10 Excellent

"Clean room, convenient location "

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

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

### On The River Inn

8/10 Good

"Everything was cool except the rude woman bartending at the 506 bistro"

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

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

### Hampton Inn Rutland

10/10 Excellent

"We had a great stay, very clean and the staff was friendly! "

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

![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07b171_y.jpg)

### Woodstock Inn & Resort

10/10 Excellent

"Always an Amazing time when we stay here. Property well maintained, staff is super friendly and the food here is above and beyond. Did I mention I got married here 👍👍"

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

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

### Mountain Sports Inn

10/10 Excellent

"Yes"

[](https://expedia.com/Killington-Hotels-Mountain-Sports-Inn.h1339833.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

8/10 Good

"Nice place close to the mountain with an attentive and friendly staff. Very clean and well run. It’s not a resort or a place where you stay to enjoy the hotel. You are here to ski / board and this is your place to return to for drinks and a good night sleep. The AC wasn’t working well when we were there but it was still late Winter so not unexpected (was unseasonably warm). The furniture in the sitting areas upstairs needs to be upgraded since that’s really the only place to hangout in morning or afternoons other than the restaurant. Overall very pleased with the place for the price."

[](https://expedia.com/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information)

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

### Turn of River Lodge

10/10 Excellent

"Super cute little place to stay"

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

![Brandon Inn](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/194828e3_y.jpg)

### Brandon Inn

10/10 Excellent

"Wonderful spot right on the town square. "

[](https://expedia.com/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information)

## Find out more about Pittsfield

**Everything you need to know about Pittsfield vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Pittsfield vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $233 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Pittsfield rentals**

At Expedia, we put the best Pittsfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

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

## Frequently asked questions

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- [Hotels in St. Johnsbury](https://expedia.com/St-Johnsbury-Hotels.d7079.Travel-Guide-Hotels)
- [Hotels in South Burlington](https://expedia.com/South-Burlington-Hotels.d6739.Travel-Guide-Hotels)
- [Burlington Cheap Hotels](https://expedia.com/Burlington-Hotels-Cheap-Hotels.0-0-d601763-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Essex Junction](https://expedia.com/Essex-Junction-Hotels.d7853.Travel-Guide-Hotels)
- [Hotels in White River Junction](https://expedia.com/White-River-Junction-Hotels.d6294.Travel-Guide-Hotels)
- [Hotels in St. Albans](https://expedia.com/St-Albans-Hotels.d6057383.Travel-Guide-Hotels)
- [Hotels in Newport](https://expedia.com/Newport-Hotels.d7047.Travel-Guide-Hotels)
- [Hotels in Montpelier](https://expedia.com/Montpelier-Hotels.d8798.Travel-Guide-Hotels)
- [Hotels in Colchester](https://expedia.com/Colchester-Hotels.d91135.Travel-Guide-Hotels)
- [Hotels in Woodstock](https://expedia.com/Woodstock-Hotels.d10868.Travel-Guide-Hotels)
- [Hotels in Springfield](https://expedia.com/Springfield-Hotels.d10292.Travel-Guide-Hotels)
- [Hotels in Manchester](https://expedia.com/Manchester-Hotels.d129374.Travel-Guide-Hotels)
- [Hotels in Williston](https://expedia.com/Williston-Hotels.d10411.Travel-Guide-Hotels)
- [Hotels in Killington](https://expedia.com/Killington-Hotels.d10780.Travel-Guide-Hotels)
- [Hotels in Burlington](https://expedia.com/Burlington-Hotels.d601763.Travel-Guide-Hotels)
- [Hotels in Middlebury](https://expedia.com/Middlebury-Hotels.d8852.Travel-Guide-Hotels)
- [Hotels in Ludlow](https://expedia.com/Ludlow-Hotels.d8496.Travel-Guide-Hotels)
- [Hotels in Warren](https://expedia.com/Warren-Hotels.d171287.Travel-Guide-Hotels)

Flights

- [Flights to Stowe](https://expedia.com/Cheap-Flights-To-Stowe.d6057386.Travel-Guide-Flights)
- [Flights to Burlington](https://expedia.com/Cheap-Flights-To-Burlington.d601763.Travel-Guide-Flights)

Cars

- [Car rentals in Burlington](https://expedia.com/Car-Rentals-In-Burlington.d601763.Car-Rental-Guide)

Activities

- [Things to do in Montpelier](https://expedia.com/Things-To-Do-In-Montpelier.d8798.Travel-Guide-Activities)

Vacation Rentals

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

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