Middlefield Holiday Rentals, Massachusetts: Private House Rentals

A snow-covered forest with a stone bridge in the background.

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

Go beyond your typical stay in Middlefield

Pet friendly

Apartment

Pool

Condo

Family friendly

Hot tub

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Middlefield hotels

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

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

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

1. Quality Inn Lee - Lenox South

Lee

Lucinda

฿3,097

฿3,459 total

includes taxes & fees

8 Nov - 9 Nov

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

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.

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

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

2. The Yankee Inn

Lenox

Basil

฿3,543

฿3,957 total

includes taxes & fees

1 Nov - 2 Nov

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

A hotel room with a bed, a desk, a chair, and a carpeted floor.

A room with a blue armchair, a wooden cabinet with a coffee maker, a television on the wall, and a small table with a cup.

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

3. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

฿3,665

฿4,094 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A covered outdoor area with stone pillars and a view of a road and green hills.

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

4. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

฿4,198

฿4,690 total

includes taxes & fees

1 Nov - 2 Nov

A hotel patio with outdoor seating and a fire pit.

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

A modern reception area with a green textured wall, a reception desk, and a coffee machine.

A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.

5. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

฿4,274

฿4,774 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A lakeside lodge with a dock, fishing rods, and outdoor seating.

A lakeside dock with kayaks and a covered boat ramp.

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

Lee

Gustavo

฿3,807

฿4,252 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Pittsfield

Ginger

฿3,175

฿3,547 total

includes taxes & fees

17 Nov - 18 Nov

A calm lake at dusk with a wooden dock and two chairs facing the water.

A small, modern room with a desk, chair, and a flat-screen TV mounted on the wall.

A two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

A room with two beds, a round mirror, a red box, and a hanging light fixture.

8. Berkshire Lake Lodge

Lee

mike

฿4,738

฿5,292 total

includes taxes & fees

1 Nov - 2 Nov

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

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

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

9. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

฿2,641

฿2,949 total

includes taxes & fees

19 Oct - 20 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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

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

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

10. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

฿3,262

฿3,643 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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.

11. Berkshires Untold

Lenox

Madhavi R

฿4,351

฿4,861 total

includes taxes & fees

1 Nov - 2 Nov

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

A spacious lobby with a fireplace, seating area, and a bar.

A garden with wooden Adirondack chairs and a stone pathway.

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

12. Berkshire Mountain Lodge

Pittsfield

Joel

฿2,892

฿3,977 total

includes taxes & fees

10 Nov - 11 Nov

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

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

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

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

13. Hotel On North

Pittsfield

Lawrence

฿4,482

฿5,007 total

includes taxes & fees

1 Nov - 2 Nov

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

14. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

฿4,801

฿5,363 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

15. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

฿5,129

฿5,883 total

includes taxes & fees

27 Oct - 28 Oct

A building with a porch and multiple windows, surrounded by purple flowers.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

A living room with a sofa, armchair, coffee table, and a patterned rug.

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

16. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

Michael

฿3,911

฿5,022 total

includes taxes & fees

20 Oct - 21 Oct

A modern hotel lobby with seating areas, tables, and a reception desk.

A kitchenette with a microwave, coffee maker, and coffee cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

A coffee station with two coffee machines and a variety of coffee pods and cups.

17. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Cynthia

฿2,774

฿3,099 total

includes taxes & fees

17 Nov - 18 Nov

A building with a flat roof, multiple windows, and a satellite dish.

A dining area with a round table set for four, surrounded by dark chairs. A white door is visible in the background, leading to a kitchen area with white appliances.

A hotel room with a large bed, a chair, a nightstand with a lamp, and a window with blinds.

An outdoor patio with a table and chairs, surrounded by wooden deck and greenery.

18. Becket Motel

Becket

Paul

฿3,677

฿5,227 total

includes taxes & fees

19 Oct - 20 Oct

A restaurant with tables and chairs, a bar area, and a view of the street outside.

A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

19. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

฿3,510

฿3,920 total

includes taxes & fees

7 Nov - 8 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 covered porch with wicker furniture and hanging flower baskets.

20. The Red Lion Inn

Stockbridge

Stephan

฿5,265

฿7,541 total

includes taxes & fees

4 Nov - 5 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Middlefield attractions

Skyline Trail

You can take time to visit Skyline Trail during your travels to Middlefield. Stroll along the area's lakeside or simply savour its cosy cafes.

See properties

Learn more about Middlefield

Explore attractions like Skyline Trail and Fox Den Wildlife Management Area as you discover things to see and do in Middlefield.

See all hotels in Middlefield

Top Middlefield Hotel Reviews

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

10/10 Excellent

"Very clean facility comfortable room and very helpful staff"

Hotel On North

10/10 Excellent

"This was an excellent hotel. Super convenient right in the middle of town, clean, huge rooms, historic, and comfortable, I would love to stay here again I would recommend it to anyone!"

The Yankee Inn

10/10 Excellent

"Well run and worth it!Hot tub closed for maintenance."

The Ellery

10/10 Excellent

"This was the perfect place to stay and visit Smith College and our daughter. It was well appointed, cozy, and comfortable. The breakfasts were delicious, the staff was hospitable and friendly and the common spaces were uplifted and quiet."

The Red Lion Inn

10/10 Excellent

"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"

Hotel Northampton

10/10 Excellent

"Historic Hotel with an old tavern. Very comfortable bed & clean room. Check in & out went smoothly."

Berkshires Untold

10/10 Excellent

"Great room and great bar. It takes time but is worth it"

The Whitlock

10/10 Excellent

"This property was the perfect location to enjoy downtown Lennox and very close to our friends’ son’s wedding at Tanglewood. I’d stay again!"

FairBridge Inn Express

10/10 Excellent

"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"

More cheap stays in Middlefield

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

฿2,376

฿2,655 total

19 Oct - 20 Oct

includes taxes & fees

5.4/10 (924 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

฿2,529

฿2,824 total

8 Nov - 9 Nov

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

฿2,641

฿2,949 total

19 Oct - 20 Oct

includes taxes & fees

7.6/10 Good! (927 reviews)

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

1055 South Street Pittsfield MA

฿3,175

฿3,547 total

17 Nov - 18 Nov

includes taxes & fees

9.4/10 Exceptional! (239 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿3,543

฿3,957 total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,004 reviews)

Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA

฿4,091

฿4,570 total

8 Nov - 9 Nov

includes taxes & fees

7.2/10 Good! (1,000 reviews)

Frequently asked questions

What's the best place for a stay in Middlefield?

Located 20.5 mi (33 km) from the heart of Middlefield, Vacation Village in the Berkshires is a top choice for your stay, based on our traveller data. Other good options for your trip to the area are Berkshire Mountain Lodge and Quality Inn Great Barrington. See all available top hotels, or vacation rentals in Middlefield.

If I need to cancel my hotel reservation in Middlefield, will I receive a refund?

Yes, most hotel reservations are refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of check in. If you booked a non-refundable reservation, you may still be able to cancel and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Middlefield.

What is staying in Middlefield like?

Visitors will definitely enjoy all that Middlefield has to offer. In Middlefield, there are 4 hotels and other accommodation options to choose from. Find out more about Middlefield.

What are the top places to visit in Middlefield?

A couple of favourite places to visit are Skyline Trail and Fox Den Wildlife Management Area. You'll also find Jacob's Pillow and Goose Pond Reservation in the area. Take a look at what more there is to see and do in Expedia's Middlefield guide.

What's the weather like in Middlefield?

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 Middlefield are January, February, November and March, with each month seeing an average of 15 cm of snowfall.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Middlefield on Expedia.com

Find hotels in Middlefield, MA from ฿2,655

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Middlefield

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Middlefield hotels

1. Quality Inn Lee - Lenox South

2. The Yankee Inn

3. Hampton Inn & Suites Berkshires-Lenox

4. Courtyard by Marriott Lenox Berkshires

5. Hilton Garden Inn Lenox Pittsfield

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

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

8. Berkshire Lake Lodge

9. Howard Johnson by Wyndham Lenox

10. Best Western Plus Berkshire Hills Inn & Suites

11. Berkshires Untold

12. Berkshire Mountain Lodge

13. Hotel On North

14. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

15. The Cornell Inn, Lenox & The Berkshires

16. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

17. Holiday Inn Express Hotel & Suites Great Barrington by IHG

18. Becket Motel

19. Holiday Inn & Suites Pittsfield-Berkshires by IHG

20. The Red Lion Inn

Stay near popular Middlefield attractions

Skyline Trail

Learn more about Middlefield

Top Middlefield Hotel Reviews

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

Hotel On North

The Yankee Inn

The Ellery

The Red Lion Inn

Hotel Northampton

Berkshires Untold

The Whitlock

FairBridge Inn Express

More cheap stays in Middlefield

FairBridge Inn Express

Quality Inn Great Barrington

Howard Johnson by Wyndham Lenox

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

The Yankee Inn

Quality Inn & Suites Northampton - Amherst

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app