Pittsfield Holiday Rentals, Vermont: Private House Rentals

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

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Our top choices for Pittsfield hotels

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

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

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.

1. The Trailside Inn

North Sherburne

Niall

฿5,341

฿5,875 total

includes taxes & fees

18 Oct - 19 Oct

A calm lake surrounded by autumn-colored trees and a clear blue sky.

A room with wooden cabinets, potted plants, and hanging light fixtures.

A bar area with wooden stools, pendant lighting, and a rustic ceiling.

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

2. Mountain Meadows Lodge

Killington

Kathy

฿5,282

฿6,648 total

includes taxes & fees

27 Oct - 28 Oct

A wooden deck with a hot tub, outdoor seating, and a view of a forested hillside.

A cozy living room with a stone fireplace, a couch, a coffee table, and a Christmas tree.

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

A bedroom with a bed, a desk, and a view of the outdoors.

3. Killington Cabin, Hot Tub & Foliage Views!

Stockbridge

฿14,485

฿24,730 total

includes taxes & fees

12 Oct - 13 Oct

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

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.

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.

4. Greenbrier Inn

Killington

Jeff

฿5,865

฿6,759 total

includes taxes & fees

18 Oct - 19 Oct

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

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

A modern kitchen with a granite countertop, a built-in oven, and a bar area with stools.

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.

5. Mountain Sports Inn

Killington

judith

฿4,661

฿5,127 total

includes taxes & fees

12 Oct - 13 Oct

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

A lodge with a fire pit, outdoor seating, and a covered area with string lights.

A spacious living room with a stone fireplace, wooden ceiling beams, and a cozy seating area.

A large, two-story log cabin with a stone foundation, multiple windows, and a balcony.

6. The Mountain Top Inn & Resort

Chittenden

Allison

฿9,891

฿10,782 total

includes taxes & fees

1 Nov - 2 Nov

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

A bathroom with a large freestanding bathtub, a mirror, and a wooden vanity.

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

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

7. North Star Lodge and Resort

Killington

Corey

฿4,436

฿4,880 total

includes taxes & fees

14 Oct - 15 Oct

A cozy living room with a stone fireplace, a round wooden coffee table, and a beige sofa.

An outdoor seating area with tables and chairs, a stone planter with flowers, and a building with a sloped roof and large windows.

A rustic interior with a stone hot tub, wooden furniture, and a mountain mural.

A pool area with lounge chairs and umbrellas, surrounded by landscaped gardens and a building with large windows.

8. Summit Lodge

Killington

Alex

฿6,880

฿8,466 total

includes taxes & fees

16 Oct - 17 Oct

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 cabin interior with a stone fireplace, wooden furniture, and a stone wall.

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

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."

9. Snowed Inn

Killington

Melissa

฿4,258

฿5,153 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

10. Best Western Inn & Suites Rutland-Killington

Rutland

Christian

฿5,402

฿5,942 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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

A lobby with a stone wall, wooden staircase, and a reception desk.

11. The Mountain Inn at Killington

Killington

Daniel

฿4,496

฿5,193 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

A cozy, rustic room with a wooden dining table, benches, and a sofa.

12. Turn of River Lodge

Killington

Jaime

฿4,024

฿4,426 total

includes taxes & fees

14 Oct - 15 Oct

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 sign for the Grand Hotel Spa in Killington, Vermont, with a mountain backdrop.

13. Killington Grand Hotel

Base Area

robert

฿7,786

฿9,133 total

includes taxes & fees

13 Oct - 14 Oct

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

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

A room with a wooden cabinet containing a television and a vintage-style mini-fridge.

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

14. Killington Haus

Killington

Timothy

฿3,651

฿4,017 total

includes taxes & fees

19 Oct - 20 Oct

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.

15. Comfort Inn Rutland - Killington

Rutland

Izatullah

฿4,131

฿4,544 total

includes taxes & fees

1 Nov - 2 Nov

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

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

16. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington

Richard

฿4,817

฿5,298 total

includes taxes & fees

2 Nov - 3 Nov

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

17. Après Inn Killington

Killington

Christian

฿4,859

฿5,344 total

includes taxes & fees

25 Oct - 26 Oct

A covered outdoor area with a wooden ceiling, potted plants, and a bench.

A hotel room with a large bed, a wooden headboard, two bedside tables with lamps, and a framed picture on the wall.

A conference room with tables, chairs, and a projector screen.

A modern kitchen with granite countertops, wooden cabinets, and a central island.

18. Hampton Inn Rutland

Rutland

Brent

฿4,532

฿4,985 total

includes taxes & fees

8 Nov - 9 Nov

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

A long corridor with tables and chairs, large windows, and a ceiling fan.

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

19. Brandon Inn

Brandon

Amelia

฿4,511

฿4,962 total

includes taxes & fees

1 Nov - 2 Nov

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

A two-story house with a balcony, surrounded by lush greenery and a pond.

A spacious living room with a large American flag, a fireplace, and a chandelier.

A kitchen with white tiled backsplash, wooden crates, and hanging pendant lights.

20. On The River Inn

West Woodstock

SARAH

฿5,471

฿6,756 total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Hotels recommended for families in Pittsfield

The Trailside Inn

North Sherburne

฿5,341

฿5,875 total

includes taxes & fees

18 Oct - 19 Oct

Mountain Meadows Lodge

Killington

฿5,282

฿6,648 total

includes taxes & fees

27 Oct - 28 Oct

Greenbrier Inn

Killington

฿5,865

฿6,759 total

includes taxes & fees

18 Oct - 19 Oct

Mountain Sports Inn

Killington

฿4,661

฿5,127 total

includes taxes & fees

12 Oct - 13 Oct

North Star Lodge and Resort

Killington

฿4,436

฿4,880 total

includes taxes & fees

14 Oct - 15 Oct

Summit Lodge

Killington

฿6,880

฿8,466 total

includes taxes & fees

16 Oct - 17 Oct

Killington Grand Hotel

Base Area

฿7,786

฿9,133 total

includes taxes & fees

13 Oct - 14 Oct

Snowed Inn

Killington

฿4,258

฿5,153 total

includes taxes & fees

25 Oct - 26 Oct

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Stay near popular Pittsfield attractions

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.

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Roger Clark Memorial Central Library

After visiting Roger Clark Memorial Central Library, make a plan to see the other sights and activities in Pittsfield.

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Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

See all hotels in Pittsfield

Top Pittsfield Hotel Reviews

My Place Hotel-Randolph VT

8/10 Good

"Bed was comfortable and the shower was great"

Mountain Sports Inn

10/10 Excellent

"This place is great!! I recommend to any travelers in that area needing a room to book it quick! Breakfast is great the rooms are super clean and the staff is very friendly and helpful."