Title: Pittsfield Vacation Rentals from $213: Search Short-Term Rentals | Expedia.com

[Pittsfield Travel Guide](https://expedia.com/Pittsfield.dx184066)[Hotels in Pittsfield](https://expedia.com/Pittsfield-Hotels.d184066.Travel-Guide-Hotels)[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

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-07-24&endDate=2026-07-26&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

![Studio | Exterior](https://images.trvl-media.com/lodging/92000000/91610000/91607600/91607556/3f477ca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Property grounds](https://images.trvl-media.com/lodging/92000000/91610000/91607600/91607556/4a308bb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Fitness facility](https://images.trvl-media.com/lodging/92000000/91610000/91607600/91607556/67e7f89c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Sauna](https://images.trvl-media.com/lodging/92000000/91610000/91607600/91607556/2584f0af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo

[](https://www.expedia.com/Killington-Hotels-Fall-Line-Small-Studio-Perfect-For-Two-On-Shuttle-Route-W-Amenities-G6a-1-Bedroom-Condo.h91607556.Hotel-Information)

Killington

[](https://www.expedia.com/Killington-Hotels-Fall-Line-Small-Studio-Perfect-For-Two-On-Shuttle-Route-W-Amenities-G6a-1-Bedroom-Condo.h91607556.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 | 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)

![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 | In-room safe, blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/122000000/121200000/121193900/121193871/66b5e2c1.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

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

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122400/125122380/47c07d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122400/125122380/7b0e71ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122400/125122380/62fa1f4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122400/125122380/dbe99dc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Killington Center 531

[](https://www.expedia.com/Killington-Hotels-Killington-Center-531.h125122380.Hotel-Information)

Killington

[](https://www.expedia.com/Killington-Hotels-Killington-Center-531.h125122380.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)

![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)

![Exterior](https://images.trvl-media.com/lodging/17000000/16350000/16341300/16341282/27dce88b.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

$254 nightly

$277 total

Apr 5 - Apr 6

Total with taxes and fees

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

![Property entrance](https://images.trvl-media.com/lodging/101000000/101000000/100996900/100996829/514eb474.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)

![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.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 8 - Apr 9

Total with taxes and fees

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

![House, Multiple Beds (Winter Lore) | Interior](https://images.trvl-media.com/lodging/73000000/72980000/72975300/72975261/6afaa2a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining room](https://images.trvl-media.com/lodging/73000000/72980000/72975300/72975261/6265a802.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Multiple Beds (Winter Lore) | Living area](https://images.trvl-media.com/lodging/73000000/72980000/72975300/72975261/fab2a030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Multiple Beds (Winter Lore) | Living area](https://images.trvl-media.com/lodging/73000000/72980000/72975300/72975261/431758ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Winter Lore

[](https://www.expedia.com/Rutland-Hotels-Winter-Lore.h72975261.Hotel-Information)

Rutland

[](https://www.expedia.com/Rutland-Hotels-Winter-Lore.h72975261.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122400/125122379/4e34a8bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122400/125122379/348c157d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122400/125122379/20e5391c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122400/125122379/7ff23a13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country

[](https://www.expedia.com/Killington-Hotels-Hotel-Style-Condo-Promising-A-Comfortable-And-Convenient-Retreat-Right-In-The-Heart-Of-Vermont-Ski-Country.h125122379.Hotel-Information)

Killington

[](https://www.expedia.com/Killington-Hotels-Hotel-Style-Condo-Promising-A-Comfortable-And-Convenient-Retreat-Right-In-The-Heart-Of-Vermont-Ski-Country.h125122379.Hotel-Information)

![House, 6 Bedrooms | Living area](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027835/1f9e32bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027835/8921270b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 3 Bedrooms | Living area](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027835/3a7dce96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027835/aab57a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Breakaway House by Killington Vacation Rentals

[](https://www.expedia.com/Killington-Hotels-Breakaway-House-By-Killington-Vacation-Rentals.h90027835.Hotel-Information)

Killington

$720 nightly

$792 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Killington-Hotels-Breakaway-House-By-Killington-Vacation-Rentals.h90027835.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=2026-04-14&endDate=2026-04-15&regionId=184066&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=CABIN)

Private vacation homes

[](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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=VACATION_HOME)

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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=CONDO)

Apartments

[](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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=APARTMENT)

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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=COTTAGE)

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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=CHALET)

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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=VILLA)

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## Top Pittsfield Hotel Reviews

![My Place Hotel-Randolph VT](https://images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/430b34b8_y.jpg)

### My Place Hotel-Randolph VT

10/10 Excellent

"This is the most convenient hotel to explore Vermont. Full kitchen and very clean rooms. Staff is quick. "

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

![Summit Lodge](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/bdef58fa_y.jpg)

### Summit Lodge

4/10 Poor

"The hotel's bar and restaurant were close. This was a big disappoint to us. We would've stayed elsewhere. Also, sleeping was. rough. Bright outside lights beam through the bedroom window and the blackout shades are not big enough to cover the whole window. We had a difficult time falling asleep and staying asleep. "

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

"."

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

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

### On The River Inn

10/10 Excellent

"I recommend it nice rooms and area around the property. Convenient for skiing. "

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

![Days Inn by Wyndham Rutland/Killington Area](https://images.trvl-media.com/lodging/1000000/890000/889600/889570/4a1f2dfa_y.jpg)

### Days Inn by Wyndham Rutland/Killington Area

4/10 Poor

"they save a lot"

[](https://expedia.com/Rutland-Hotels-Days-Inn-By-Wyndham-RutlandKillington-Area.h889570.Hotel-Information)

![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/f9bd2dd9_y.jpg)

### Killington Mountain Lodge, Tapestry Collection by Hilton

8/10 Good

"Convenient location but it is not ski in ski out as described in listing. "

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

![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/17fcad53_y.jpg)

### North Star Lodge and Resort

10/10 Excellent

"We just stayed one night at this hotel. The room was just outdated but pretty clean. We did notice on the morning there were two beers from the night before. They also have an outdoor heated pool that we didn't get to check out because it was raining but you can see Killington from the pool on clearer days."

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

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

### Mountain Sports Inn

10/10 Excellent

"Nice quiet Clean rooms and plenty of parking. "

[](https://expedia.com/Killington-Hotels-Mountain-Sports-Inn.h1339833.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, comfortable bed Great steakhouse next door"

[](https://expedia.com/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.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 $213 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.

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- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
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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

### Can I find a vacation rental in Pittsfield?

### What are some of the best vacation rentals that Pittsfield has to offer?

### How many vacation rentals are there in Pittsfield?

### What can I see and do in Pittsfield?

### What are vacation rentals like in Pittsfield?

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Flights

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Cars

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

Activities

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Vacation Rentals

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