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

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

A hotel room with a bed, a desk, a chair, a kitchenette, and a framed picture on the wall.

1. My Place Hotel-Randolph VT

Randolph Center

Whitney

3.639.737 ₫

3.967.314 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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

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

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

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

2. The Mountain Inn at Killington

Killington

Christopher

3.483.113 ₫

4.023.112 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

3. Mountain Sports Inn

Killington

Tom

3.350.646 ₫

3.685.711 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

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

4. North Star Lodge and Resort

Killington

Corey

3.599.996 ₫

3.959.996 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

An indoor swimming pool with clear blue water, surrounded by white tiles and blue pillars.

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

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

5. Comfort Inn Rutland - Killington

Rutland

Reuben

3.089.867 ₫

3.398.853 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

6. Turn of River Lodge

Killington

Jaime

3.067.056 ₫

3.373.762 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

A spacious living room with a high ceiling, wooden beams, a staircase, and a large window.

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.

7. Greenbrier Inn

Killington

Hilary

4.379.382 ₫

5.047.238 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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

A cozy living room with a stone fireplace, leather sofas, a round coffee table, and a large window offering a view of the outdoors.

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

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

8. Mountain Meadows Lodge

Killington

caroline

3.582.854 ₫

4.590.385 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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

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

9. Hampton Inn Rutland

Rutland

Brent

3.982.853 ₫

4.381.139 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

A two-story house with a snow-covered roof and a front porch.

10. On The River Inn

West Woodstock

Laura

6.155.319 ₫

7.342.331 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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

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

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

A modern gym with a large window, wooden paneling, and illuminated vertical lights.

11. Emrose Luxury Cabins

Brandon

Michael

4.207.788 ₫

4.754.801 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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

12. The Trailside Inn

North Sherburne

Niall

4.140.526 ₫

4.554.579 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A large, multi-story hotel with a covered entrance and multiple windows.

A hotel room with a fireplace, a bed with red bedding, a red armchair, a wooden coffee table, and a kitchenette.

A lobby with a sofa, armchairs, and a coffee table. There is a painting on the wall and a door in the background.

A digital display in a hotel lobby showing the local weather and news.

13. Courtyard Middlebury

Middlebury

Nikhil

4.649.346 ₫

5.114.280 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

14. Brandon Inn

Brandon

Sharon

3.545.451 ₫

3.899.996 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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

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

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

A two-story lodge with a stone facade, wooden balconies, and a well-maintained lawn.

15. Summit Lodge

Killington

Alex

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.

A room with a bed, a wooden wall-mounted bike rack, a microwave, a coffee maker, and a small refrigerator.

16. Après Inn Killington

Killington

Christian

4.002.593 ₫

4.402.852 ₫ 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 Best Western Inn & Suites with a well-maintained lawn, a parking area, and a building with a porch.

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

17. Best Western Inn & Suites Rutland-Killington

Rutland

Christian

4.184.671 ₫

4.603.138 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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

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

A reception desk with a wooden finish, a black textured wall, and a blue mat with 'Days Inn' text.

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.

18. Days Inn by Wyndham Rutland/Killington Area

Rutland

Charlotte

3.068.828 ₫

3.375.711 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

A cozy living room with a stone fireplace, leather sofa, and a patterned rug.

19. The Mountain Top Inn & Resort

Chittenden

cynthia

7.175.317 ₫

7.821.096 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

A patio area with a fire pit, outdoor seating, and a swimming pool.

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.

20. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington

Richard

4.238.437 ₫

4.662.280 ₫ 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

Emrose Luxury Cabins

10/10 Excellent

"This is a unique property. Very clean, great shampoos, comfortable beds. Bring your own food and snacks. The grounds are super clean and in a safe, private area. We had an issue with the arrival instructions not opening in email but a call to the property phone number got our issue resolved quickly. Everything was great."

Comfort Inn Rutland - Killington

8/10 Good

"Only there for one night. Good clean room with friendly and knowledgeable staff."

The Mountain Inn at Killington

8/10 Good

"The property is beautiful and it’s convenient to the golf course. The rooms small but clean. Not a lot of privacy in the bathroom due to sliding door. Also, no coffee machines in the room"

Mountain Meadows Lodge

10/10 Excellent

"This place was beautifully decorated. Bed was very comfortable, hot tub, and sitting by the lake was phenomenal. The community jigsaw puzzle was a nice touch. The breakfast was delicious and a staff of super nice. We’ve never had an experience like that at a hotel."

The Shire Woodstock

10/10 Excellent

"Great views"

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent

"Great outdoor hot tub"

Sleep Woodstock Motel

10/10 Excellent

"This place is amazing! Keyless check-in and entry was a breeze. Will stay again. Loved it!"

North Star Lodge and Resort

10/10 Excellent

"We love staying here. The staff are friendly. Great coffee. Heated pool."

Woodstock Inn & Resort

10/10 Excellent

"Wonderful inn! Everything was wonderful: rooms, food, etc!!"

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