Hotels with Parking in Pittsfield

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Hotels with Parking in Pittsfield

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Pittsfield on Hotels.com. These Pittsfield Hotels with Parking consistently deliver on quality, location and traveler experience. Last updated on September 24, 2026.

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

A wooden cabin with a white door labeled "Outer Limits," a covered porch, and a snow-covered deck.

A spacious living room with a wooden dining table, a sofa, and a coffee table. There is a large rug on the floor and a fireplace in the background.

A kitchen with wooden cabinets, a refrigerator, a stove, a microwave, and a sink.

1. Mountain Sports Inn

Killington

CNY864

CNY951 total

includes taxes & fees

Sep 29 - Sep 30

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

A cozy living room with a fireplace, a white sofa, a coffee table with candles, and a bag with the text "Love is All Around".

A cozy living room with a stone fireplace, wooden furniture, and a television.

A large building with a covered entrance and multiple windows, surrounded by a grassy area and trees with autumn foliage.

2. The Trailside Inn

North Sherburne

CNY1,069

CNY1,176 total

includes taxes & fees

Oct 18 - Oct 19

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

A bar area with a star sign, bicycles, and a patterned carpet.

A snow-covered road with a sign reading 'Welcome to Killington.'

A multi-story building with a pool and a covered patio area.

3. North Star Lodge and Resort

Killington

CNY930

CNY1,023 total

includes taxes & fees

Sep 27 - Sep 28

A table with a checkered placemat, a red vase with greenery and berries, and a clear plastic bag with items.

A spacious loft-style living area with a high ceiling, wooden beams, and a cozy fireplace. A staircase with a wooden railing leads to an upper level.

A sign for Greenbrier Inn and a gift shop, with a snow-covered ground.

A wooden interior with a staircase, a dining area, and a living room with a sofa and a lamp.

4. Greenbrier Inn

Killington

CNY1,045

CNY1,205 total

includes taxes & fees

Oct 20 - Oct 21

A cozy living room with a stone fireplace, a television, and a coffee table with a vase of flowers.

A rustic lodge with a stone chimney, surrounded by autumn foliage.

A grassy area with two red Adirondack chairs and a white truck parked in front of a wooden building with a mountain backdrop.

A cozy, warmly lit room with wooden walls, a wooden reception desk, a floral sofa, and a Christmas tree.

5. Turn of River Lodge

Killington

CNY792

CNY871 total

includes taxes & fees

Sep 27 - Sep 28

A building with a modern design, featuring large windows and a covered outdoor seating area.

A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs, a piano, and a view of the outside.

A hotel room with two beds, a wooden headboard, a desk, and a window with a view of greenery.

A swimming pool surrounded by snow, with a building in the background.

6. The Mountain Inn at Killington

Killington

CNY900

CNY1,039 total

includes taxes & fees

Oct 19 - Oct 20

A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

A cozy living room with a fireplace, wooden furniture, and a stone wall.

A wooden interior with a dining area featuring a round table and benches, large windows with a view of greenery, and a sign that reads "Grateful."

A golf course with a winding road, surrounded by trees and mountains.

7. Snowed Inn

Killington

CNY1,007

CNY1,218 total

includes taxes & fees

Oct 25 - Oct 26

A sign for 'Apres Inn' in KILLINGTON, VT, with a modern building featuring large windows and a balcony.

A kitchen with a stove, oven, microwave, sink, and cabinets.

A sign for a hotel named 'Après Inn' in Killington, VT, indicating a vacancy.

A hotel room with two beds, a TV, a desk with a chair, and a window with curtains.

8. Après Inn Killington

Killington

CNY1,034

CNY1,138 total

includes taxes & fees

Oct 25 - Oct 26

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.

A modern hotel lobby with a dining area, stone wall, and a view of the outside.

A kitchen with wooden cabinets, a stainless steel refrigerator, a stove, and two bar stools.

A Best Western Inn & Suites with a well-maintained lawn, a parking area, and a building with a porch.

9. Best Western Inn & Suites Rutland-Killington

Rutland

CNY1,081

CNY1,189 total

includes taxes & fees

Oct 21 - Oct 22

A hotel lobby with a reception desk, seating area, and a coffee table with a fruit basket.

A modern hotel lobby with a blue sofa, a round coffee table, and abstract art on the walls.

A hotel room with two beds, a desk, a chair, a lamp, and a trash can.

A brick building with a sign reading 'Southside Steakhouse' and the number '170' above the entrance.

10. Comfort Inn Rutland - Killington

Rutland

CNY852

CNY937 total

includes taxes & fees

Oct 25 - Oct 26

A wooden structure with a black door labeled "KILLINGTON HAUS GUEST ENTRANCE" and a sign saying "WELCOME GUESTS!".

A modern interior with a kitchen area, seating, and a fireplace.

A wall with a colorful mural featuring the text "Greetings from KELINGTON, VERMONT."

A bedroom with a red bed, white bedding, a window with blinds, a desk with a chair, and a wall-mounted lamp.

11. Killington Haus

Killington

CNY731

CNY804 total

includes taxes & fees

Oct 19 - Oct 20

A garden entrance with a white pergola covered in ivy, a sign indicating the pool is open, and outdoor seating with umbrellas.

A paved patio with outdoor furniture, a decorative garden bed, and a white fence.

A large house with a swimming pool, a fenced yard, and a well-lit entrance.

12. Brandon Inn

Brandon

CNY916

CNY1,008 total

includes taxes & fees

Oct 22 - Oct 23

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

A hotel room with two beds, a desk, and a chair. The room has a wooden floor and red walls with framed pictures.

A row of cabins with a river in the foreground, surrounded by trees and a snowy landscape.

A red car parked at a charging station in front of a building with a 'OPEN' sign.

13. Sleep Woodstock Motel

Woodstock

CNY634

CNY956 total

includes taxes & fees

Sep 27 - Sep 28

A modern bedroom with a curved wall, a bed, a sofa, a small table with flowers, and a walk-in closet.

A campground with several wooden cabins, a central fire pit area, and a well-maintained lawn.

A swimming pool at dusk with surrounding lounge chairs and a covered area with lights.

A modern living room with a sofa, two round tables, a fireplace, and a television.

14. Emrose Luxury Cabins

Brandon

CNY1,087

CNY1,229 total

includes taxes & fees

Sep 27 - Sep 28

A spacious living area with a fireplace, leather sofas, and a dining area with wooden furniture.

A spacious dining area with wooden tables and chairs, large windows offering a view of the outdoors, and a modern interior design with a wooden ceiling.

A hotel room with two beds, a large beach mural on the wall, and a wooden floor.

An indoor swimming pool with a high ceiling, multiple ceiling fans, and a seating area with chairs and tables.

15. Days Inn by Wyndham Rutland/Killington Area

Rutland

CNY793

CNY872 total

includes taxes & fees

Oct 25 - Oct 26

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

A room with a high ceiling, wooden beams, and a carpeted floor. There are several wooden tables and chairs arranged for dining.

A bedroom with a large bed, two bedside tables, a small table, and a window with curtains.

A small outdoor structure with a metal roof, a chimney, and a stack of wood.

16. Inn at Neshobe River

Brandon

CNY1,172

CNY1,290 total

includes taxes & fees

Sep 26 - Sep 27

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

A modern lounge area with orange upholstered chairs, a fireplace, and large windows offering a view of autumn trees.

A hotel entrance with a covered walkway, stone pillars, and a sign reading "Haywood Inn."

A hotel room with a bed, a TV, a fireplace, a desk, and a chair.

17. Hampton Inn Rutland

Rutland

CNY1,002

CNY1,102 total

includes taxes & fees

Oct 25 - Oct 26

A covered outdoor seating area with stone pillars and wooden beams, surrounded by a grassy lawn and trees.

A modern restaurant with a bar area, seating arrangements, and a kitchen in the background.

A multi-story hotel with a parking lot, surrounded by autumn-colored trees and mountains in the background.

18. My Place Hotel-Randolph VT

Randolph Center

CNY1,299

CNY1,416 total

includes taxes & fees

Oct 25 - Oct 26

A large, multi-story hotel with a prominent entrance and a staircase leading to the upper levels.

A stone fireplace with a modern seating area, including a sofa and chairs, a coffee table, and a decorative bowl.

A hotel with a pool, multiple balconies, and a snow-covered ground.

A spacious loft-style living area with high ceilings, exposed wooden beams, and a mezzanine level.

19. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington

CNY1,095

CNY1,205 total

includes taxes & fees

Oct 25 - Oct 26

A bench with snow accumulation, a fire pit with visible flames, and a wooden fence in the background.

A pool area with lounge chairs and a view of a mountainous landscape.

A reception desk with a stone wall backdrop and wooden accents, a person with a suitcase, and a television screen above the desk.

A spacious lobby with leather seating, a stone fireplace, and a staircase leading to an upper level.

20. Killington Grand Hotel

Base Area

CNY1,556

CNY1,825 total

includes taxes & fees

Oct 14 - Oct 15

See more properties

Top landmarks in Pittsfield

Pittsfield Town Hall

Pittsfield Town Hall is worth a visit when in central Pittsfield.

Roger Clark Memorial Central Library

Roger Clark Memorial Central Library is worth a visit when in central Pittsfield.

Keep exploring

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