Richmond Holiday Rentals, Massachusetts: Private House Rentals

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Our top choices for Richmond hotels

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

1. The Yankee Inn

Lenox

Basil

2.748.792 ₫

3.070.402 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

A conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.

A room with a blue armchair, an orange armchair, a round table, a floor lamp, and a wardrobe.

2. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

2.843.444 ₫

3.176.128 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

3. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

3.257.319 ₫

3.638.425 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A garden with wooden Adirondack chairs and a stone pathway.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

4. Berkshire Mountain Lodge

Pittsfield

Kathleen

2.222.957 ₫

3.062.364 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

A cozy library with bookshelves, a fireplace, and comfortable seating.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

5. Berkshires Untold

Lenox

Madhavi R

3.376.067 ₫

3.771.067 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

A hotel patio with outdoor seating and a fire pit.

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

6. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

3.308.511 ₫

3.695.556 ₫ total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

A snack bar with shelves of snacks and a refrigerated display.

7. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Ginger

2.567.268 ₫

2.867.638 ₫ total

includes taxes & fees

10 Nov - 11 Nov

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lakeside dock with kayaks and a covered boat ramp.

A dining area with large windows, wooden furniture, and a view of a lake.

A lodge with a large building and a dock by a lake, surrounded by forest.

8. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Gustavo

2.975.697 ₫

3.323.853 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A dining area with a glass table, red walls, and framed artwork.

A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

9. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

3.970.214 ₫

4.553.835 ₫ total

includes taxes & fees

28 Oct - 29 Oct

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

10. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

2.043.888 ₫

2.283.022 ₫ total

includes taxes & fees

22 Oct - 23 Oct

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

11. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

2.424.123 ₫

2.707.745 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A bar with wooden floors and shelves filled with bottles.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

12. The Red Lion Inn

Stockbridge

Stephan

4.084.808 ₫

5.851.032 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A large house with a covered patio area featuring outdoor seating and a fire pit.

A cozy lounge area with plush seating, a fireplace, and large windows offering a view of the outdoors.

A corner dining area with a wooden table set for four, surrounded by upholstered chairs.

A well-lit room with a large window, a clock, and a fireplace. There are several chairs and a table with a vase.

13. The Whitlock

Lenox

Michael

3.777.312 ₫

4.219.258 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

An outdoor seating area with Adirondack chairs and a fire feature.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

14. Element by Marriott Lenox Berkshires

Lenox

Kirsty

3.708.276 ₫

4.142.145 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A red building with a sign reading "Shaker Mill Inn."

A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

15. Shaker Mill Inn

West Stockbridge

Steven

3.415.104 ₫

3.746.369 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

16. Quality Inn Lee - Lenox South

Lee

Christine

2.402.600 ₫

2.683.704 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A building entrance with a large planter with purple flowers and a small tree.

A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

A library with bookshelves, a television, and two armchairs.

17. Hotel On North

Pittsfield

Lawrence

3.477.481 ₫

3.884.346 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A garden with a white gazebo, a brick pathway, and various plants and flowers.

A breakfast buffet with various dishes and beverages.

A spacious living room with a grand piano, a red armchair, and a chandelier.

A courtyard with stone steps, potted plants, and a small wooden structure.

18. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

4.877.809 ₫

5.448.572 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

A dining table set with a vase of flowers, a book, and cutlery.

A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

19. Brook Farm Inn

Lenox

Carrie

5.032.363 ₫

5.828.186 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A group of people performing yoga in an outdoor setting with grass and trees.

A hotel room with a flat-screen TV, a microwave, a refrigerator, a wooden dresser, a bedside lamp, and a framed picture on the wall.

A hotel room with a bed, two chairs, a small table, and a lamp.

A motel with a row of rooms, a parking lot, and a hilly backdrop.

20. Pleasant Valley Motel West Stockbridge

West Stockbridge

James

1.773.008 ₫

1.944.990 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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Stay near popular Richmond attractions

Lenox Mountain

10.0/10 (2 reviews)

Commune with nature and explore the great outdoors at Lenox Mountain during your travels in Richmond. Wander the lakeside in this quaint area.

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Furnace Brook Winery at Hilltop Orchards

10.0/10 (1 review)

You can enjoy a tasting or tour at Furnace Brook Winery at Hilltop Orchards during your travels to Richmond. Wander the lakeside in this family-friendly area.

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Fairfield Brook WMA

You can take time to visit Fairfield Brook WMA during your travels to Richmond. Discover the mountain views while you're in the area.

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Lenox Mountain Reserve

You can take time to visit Lenox Mountain Reserve during your travels to Richmond. Discover the mountain views while you're in the area.

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Nordeen Marsh Natural Heritage Area

You can take time to visit Nordeen Marsh Natural Heritage Area during your travels to Richmond. Discover the mountain views while you're in the area.

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Richmond Conservation

You can take time to visit Richmond Conservation during your travels to Richmond. Discover the mountain views while you're in the area.

See properties

Balderdash Cellars

You can enjoy a tasting or tour at Balderdash Cellars during your travels to Richmond. Discover the mountain views while you're in the area.

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Richmond Free Public Library

After visiting Richmond Free Public Library, make a plan to see the other sights and activities in Richmond. Discover the mountain views while you're in the area.

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Learn more about Richmond

Get away to relaxing Richmond! Enjoy the horse riding, wineries and local cuisine.

See all hotels in Richmond

A forested area with a calm lake and a wooden bridge.

Top Richmond Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Amazing pool and great full kitchens in rooms."

Hotel On North

10/10 Excellent

"This is a great hotel.. likely the best place to stay in Pittsfield. Just an overnight stop so not time to get a good read on the area but a good option for the Berkshires if you you don't want to pay the Lenox/Stockbridge premium."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"O"

The Yankee Inn

8/10 Good

"Everything at the Yankee Inn was very good with the exception of, wasn’t the most comfortable bed I’ve ever slept in, but everything else was very good"

Quality Inn Great Barrington

10/10 Excellent

"Beds were comfortable, room was clean, train was not often"

Berkshire Mountain Lodge

10/10 Excellent

"The room was fantastic. Great place to stay in the Berkshires. The hot tub wasn't working, but things happen. Other than that, it was a perfect stay."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"It's a perfect stop on our little Berkshires trip. The Inn had everything we needed and more. The property was beautiful, and the staff was beyond helpful. We will certainly be back."

The Red Lion Inn

8/10 Good

"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"It was good"

More cheap stays in Richmond

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.606.651 ₫

1.794.629 ₫ total

15 Oct - 16 Oct

includes taxes & fees

5.4/10 (923 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

2.012.583 ₫

2.248.055 ₫ total

10 Nov - 11 Nov

includes taxes & fees

8.6/10 Excellent! (1,006 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

2.043.888 ₫

2.283.022 ₫ total

22 Oct - 23 Oct

includes taxes & fees

7.6/10 Good! (923 reviews)

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

1055 South Street Pittsfield MA

2.567.268 ₫

2.867.638 ₫ total

10 Nov - 11 Nov

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.748.792 ₫

3.070.402 ₫ total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,005 reviews)

The Whitlock

16 Church St Lenox MA

3.777.312 ₫

4.219.258 ₫ total

2 Nov - 3 Nov

includes taxes & fees

Hotels in Richmond with star rating

Frequently asked questions

What's the seasonal weather like in Richmond?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Richmond are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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Book Hotels in Richmond on Expedia.com

Find hotels in Richmond, MA from 1.794.629 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Richmond

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Richmond hotels

1. The Yankee Inn

2. Hampton Inn & Suites Berkshires-Lenox

3. Courtyard by Marriott Lenox Berkshires

4. Berkshire Mountain Lodge

5. Berkshires Untold

6. Hilton Garden Inn Lenox Pittsfield

7. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8. The Black Swan Lee - Lenox, an Ascend Collection Hotel

9. The Cornell Inn, Lenox & The Berkshires

10. Howard Johnson by Wyndham Lenox

11. Best Western Plus Berkshire Hills Inn & Suites

12. The Red Lion Inn

13. The Whitlock

14. Element by Marriott Lenox Berkshires

15. Shaker Mill Inn

16. Quality Inn Lee - Lenox South

17. Hotel On North

18. Whistler's Inn Bed & Breakfast

19. Brook Farm Inn

20. Pleasant Valley Motel West Stockbridge

Stay near popular Richmond attractions

Lenox Mountain

Furnace Brook Winery at Hilltop Orchards

Fairfield Brook WMA

Lenox Mountain Reserve

Nordeen Marsh Natural Heritage Area

Richmond Conservation

Balderdash Cellars

Richmond Free Public Library

Learn more about Richmond

Top Richmond Hotel Reviews

Vacation Village in the Berkshires

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Yankee Inn

Quality Inn Great Barrington

Berkshire Mountain Lodge

The Cornell Inn, Lenox & The Berkshires

The Red Lion Inn

Hampton Inn & Suites Berkshires-Lenox

More cheap stays in Richmond

FairBridge Inn Express

Quality Inn Great Barrington

Howard Johnson by Wyndham Lenox

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

The Yankee Inn

The Whitlock

Hotels in Richmond with star rating

Frequently asked questions

Explore a world of travel with Expedia

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