A lake surrounded by autumn-colored trees and a rocky shoreline.

Pittsfield Vacation Rentals

Where to?

Dates

November 2026

December 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Pittsfield vacation rentals

A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

1. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Stockbridge

Kevin M.

SAR 2,036 total

includes taxes & fees

8 Nov - 9 Nov

2. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Stockbridge

Sophie L.

SAR 2,036 total

includes taxes & fees

8 Nov - 9 Nov

A wooden shed with a cross-braced door in a garden with a house in the background.

3. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

North Sherburne

Matthew R.

SAR 1,457 total

includes taxes & fees

8 Nov - 9 Nov

A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

4. Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge

Gerald S.

SAR 1,724 total

includes taxes & fees

18 Nov - 19 Nov

A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

5. Luxury Condo Tucked in the Heart of Killington

Killington

"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...

Melinda D.

SAR 926 total

includes taxes & fees

8 Nov - 9 Nov

A residential area with houses, a swimming pool, and a mountain backdrop.

6. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

Killington

Nathan H.

SAR 877 total

includes taxes & fees

8 Nov - 9 Nov

A spacious living area with a wooden ceiling, a sofa, a chair, a television, and a staircase.

7. Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you

Chittenden

SAR 732 total

includes taxes & fees

6 Nov - 7 Nov

A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

8. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Killington

Spencer P.

SAR 1,326 total

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a large bed, a TV mounted on the wall, and a sliding door leading to a bathroom.

9. Jack S`Bearo - Slopes, Fireplace, Pool

Killington

Joseph S.

SAR 961 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

10. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Killington

John O.

SAR 1,409 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with stainless steel appliances, a dining area with a wooden table, and a cozy seating area with a fireplace.

11. The Sunup Suite at Killington: 2RM/2BA Condo w/ Pool. Bus Route. Discounted Ski Rentals!

Killington

Catherine N.

A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

12. Mountain Green ground-floor condo with private yard off the patio

Killington

SAR 1,102 total

includes taxes & fees

7 Nov - 8 Nov

13. The Suites at Killington Center

Killington

SAR 1,764 total

includes taxes & fees

8 Nov - 9 Nov

A cozy living room with a stone fireplace, leather sofas, and a framed sign on the wall.

14. Robins Nest- FirePlace, Near Pico, Pool

Killington

Leslie D.

A modern living room with a stone fireplace, a flat-screen TV mounted above it, wooden flooring, and a kitchen area in the background.

15. Modern Killington Farmhouse Condo: Close to it all! 412

Killington

Tyler L.

SAR 1,273 total

includes taxes & fees

8 Nov - 9 Nov

A gym with exercise equipment, colorful exercise balls, and a mirrored wall.

16. Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

The Woods

Keaton S.

A rustic interior with a stone fireplace, wooden beams, leather furniture, and a balcony with a view.

17. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Killington

Kathleen M.

A living room with a sofa, coffee table, and fireplace. There is a large window and a balcony with outdoor furniture.

18. FirBear- Pool, Gym, Fireplace, Hot tub!

The Woods

Kristin G.

An indoor swimming pool with a hot tub, surrounded by a forest-themed mural, and a metal ladder for access.

19. SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace

The Woods

Brittany R.

SAR 1,468 total

includes taxes & fees

9 Nov - 10 Nov

A living room with a fireplace, a sofa, a coffee table, and a television.

20. Mountain Green high-floor front condo in Building 3 with ski trail views

Killington

Jason B.

SAR 1,435 total

includes taxes & fees

7 Nov - 8 Nov

View all properties

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

A spacious living room with a stone fireplace, wooden furniture, and a large potted plant.

The Trailside Inn

North Sherburne

10/10 Excellent

I've never wrote a review on any product or hotel until now and that is because the Trailside Inn deserves all the recognition it could get! To start, the owners Josh and Ann are fantastic. We arrived Friday night after a long drive from Long Island - we were immediately greeted by Josh who welcomed us to the lodge and took the time to show us the best trails at Killington and offered advice on restaurants near by. It was very cold Saturday so we didn't stay long at the mountain. When we...

Alyssa

A wooden dock with two Adirondack chairs and a blanket, overlooking a calm lake with dense forest in the background.

Mountain Meadows Lodge

Killington

10/10 Excellent

Timothy

Snowed Inn

Killington

10/10 Excellent

Tammy

A spacious room with large windows, a stone wall, and a wooden ceiling.

The Mountain Top Inn & Resort

Chittenden

10/10 Excellent

We only stayed for two nights but could not have been happier! The staff was extremely helpful and friendly. The views and grounds are beautiful. We loved the beautiful, quiet setting. It rained one of the days we were at the hotel, but the staff was eager to give recommendations of places to go for other indoor activities! We were extremely pleased to visit the Mountain Top Inn and will definitely return for another stay!

Anonymous traveler

A dining area with a wooden table and chairs, a fireplace, and a cozy seating area with a couch and a TV.

Mountain Sports Inn

Killington

10/10 Excellent

Julianne

Après Inn Killington

Killington

10/10 Excellent

Anonymous traveler

A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a view of the outdoors.

North Star Lodge and Resort

Killington

10/10 Excellent

Thayer

A spacious indoor area with a large dining table, several chairs, and a sofa. There is a glass door leading outside, and the room has a wooden ceiling structure.

Best Western Inn & Suites Rutland-Killington

Rutland

10/10 Excellent

Judie

A modern interior with a wooden reception desk, seating area, and large windows.

Hampton Inn Rutland

Rutland

10/10 Excellent

Anonymous traveler

A large, two-story house with a driveway leading to a garage, surrounded by a well-maintained lawn and autumn-colored trees.

The Lilac Inn

Brandon

10/10 Excellent

Karen

A two-story house with a porch, surrounded by trees.

Inn at Neshobe River

Brandon

10/10 Excellent

Anonymous traveler

A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

Sleep Woodstock Motel

Woodstock

10/10 Excellent

We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room...

John

A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.

On The River Inn

West Woodstock

10/10 Excellent

Ayleen

A two-story building with a porch, outdoor seating, and flags.

Green Trails Inn

Brookfield

10/10 Excellent

Jesus

Frequently Asked Questions

Can I find a vacation rental in Pittsfield?

Yes, there are vacation rentals close to popular sights in Pittsfield, or you can choose a more remote option if you're looking for relaxation. Pittsfield is known for its bars and restaurants.

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

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.: This vacation home rental outside Pittsfield is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Pittsfield?

Expedia has 28 vacation rentals for your stay in Pittsfield.

What can I see and do in Pittsfield?

While exploring the area, visit family-friendly sights like Killington Adventure Center, or get outside and enjoy nature at Green Mountain National Forest. Pittsfield Town Hall and Roger Clark Memorial Central Library are other places to visit while you're in town.

What are vacation rentals like in Pittsfield?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Pittsfield. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a small group gathering.

Pittsfield Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pittsfield vacation rentals

1. Ski Home/Arcade Mountain Views Near Killington/Woodstock

2. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

3. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

4. Gnome Home Mountain Ski Chalet w/Sauna Killington

5. Luxury Condo Tucked in the Heart of Killington

6. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

7. Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you

8. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

9. Jack S`Bearo - Slopes, Fireplace, Pool

10. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

11. The Sunup Suite at Killington: 2RM/2BA Condo w/ Pool. Bus Route. Discounted Ski Rentals!

12. Mountain Green ground-floor condo with private yard off the patio

13. The Suites at Killington Center

14. Robins Nest- FirePlace, Near Pico, Pool

15. Modern Killington Farmhouse Condo: Close to it all! 412

16. Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

17. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

18. FirBear- Pool, Gym, Fireplace, Hot tub!

19. SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace

20. Mountain Green high-floor front condo in Building 3 with ski trail views

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

The Trailside Inn

10/10 Excellent

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?