Western Massachusetts Holiday Rentals, Massachusetts: Private House Rentals

A lake with a rocky shoreline and a forested island.

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Our top choices for Western Massachusetts hotels

A modern hotel lobby with a stone wall, a fireplace, a bar area, and seating arrangements.

A modern lounge area with a stone wall, a fireplace, a sofa, and two blue armchairs.

A modern kitchen with stainless steel appliances, a microwave, and a dishwasher. There is a dining area with a table and chairs.

An outdoor seating area with chairs and tables, a covered patio with string lights, and potted plants.

1. Homewood Suites by Hilton Hadley Amherst

Hadley

Rebecca

฿5,220

฿5,830 total

includes taxes & fees

1 Nov - 2 Nov

A hotel with a covered entrance, a flag, and a sign.

A spacious living area with a fireplace, sofas, and a coffee table.

A hotel room with a sofa, a small table, a red stool, a kitchenette, and a bed.

A hotel room with a bed, a sofa, a round coffee table, and a nightstand.

2. Comfort Inn & Suites Hadley - Amherst

Hadley

John

฿3,945

฿4,406 total

includes taxes & fees

4 Nov - 5 Nov

A modern living room with a stone fireplace, a white sofa, a round coffee table, and a green armchair.

An indoor swimming pool with clear glass walls, a poolside seating area, and a reception desk.

A modern hotel dining area with multiple tables and chairs, pendant lighting, and a view of the city through large windows.

A reception area with a counter, a refrigerator stocked with snacks, and a wall with a tree pattern.

3. Fairfield Inn & Suites Springfield Northampton/Amherst

Northampton

rob

฿4,838

฿5,404 total

includes taxes & fees

25 Oct - 26 Oct

A modern living room with a fireplace, red curtains, and a wooden dining table.

A registration desk with a sign above it, a receptionist, and several people standing in line.

A modern building with a grid-like facade, multiple balconies, and a spacious courtyard with geometric sculptures.

A modern hotel lobby with a large TV screen displaying the hotel name, red chairs, wooden shelves, and a clock on the wall.

4. Hotel UMass

Amherst

Lisa

฿3,695

฿4,174 total

includes taxes & fees

7 Oct - 8 Oct

A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.

An outdoor cafe with tables and chairs, surrounded by hanging flower baskets and a brick building in the background.

A hotel room with a desk, chair, lamp, and a large mirror. There is a staircase leading to an outdoor area with a railing.

A hotel lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.

5. Hotel Northampton

Northampton

Beth

฿4,168

฿4,656 total

includes taxes & fees

12 Oct - 13 Oct

A large, historic building with a prominent tower and a well-lit entrance labeled "Bollywood".

A spacious living room with a fireplace, comfortable seating, and elegant chandeliers.

A spacious outdoor seating area with a fire feature, white brick walls, and multiple windows with shutters.

A long dining table set with white tableware, flanked by windows and a skylight.

6. Inn on Boltwood

Amherst

pam

฿5,764

฿6,438 total

includes taxes & fees

3 Nov - 4 Nov

An outdoor seating area with wicker furniture, a fire pit, and decorative lamps.

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

A dining table set with multiple wine glasses, a centerpiece with flowers, and candles.

A spacious lobby with a central seating area, a reception desk, and a television screen.

7. Courtyard by Marriott Hadley Amherst

Hadley

Yuki

฿4,820

฿5,384 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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.

8. The Yankee Inn

Lenox

William

฿3,557

฿3,973 total

includes taxes & fees

1 Nov - 2 Nov

A breakfast area with a waffle station, coffee machine, and various food options.

A modern hotel room with a large bed, a desk, and a chair.

A modern hotel room with a flat-screen TV on a wooden desk, a blue office chair, and a large window with abstract art.

9. Tru by Hilton Chicopee Springfield

Chicopee

Laura

฿3,680

฿4,175 total

includes taxes & fees

1 Nov - 2 Nov

A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.

A brick building with a sign reading "The Ellery."

A hotel room with a bed, a sofa, a dining table, and a chair. There are two nightstands with lamps and a framed picture on the wall.

A modern hotel room with a bed, sofa, dining table, and chairs.

10. The Ellery

Northampton

Travis

฿4,266

฿4,765 total

includes taxes & fees

27 Oct - 28 Oct

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.

An outdoor seating area with stone fire pit, chairs, and a red building in the background.

A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

A spacious living area with a fireplace, wooden beams, and a large window.

11. The Williams Inn

Williamstown

Soleil

฿6,267

฿7,000 total

includes taxes & fees

2 Nov - 3 Nov

A bar area with wooden tables and chairs, a central bar counter with taps, and a brick wall with shelves of bottles and glasses.

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

A casino with multiple blackjack tables, slot machines, and a large chandelier.

A modern hotel lobby with leather furniture, a bar area, and a large TV screen.

12. MGM Springfield

Metro Center

Carla

฿5,000

฿6,434 total

includes taxes & fees

1 Nov - 2 Nov

A Fairfield Inn & Suites by Marriott hotel with a modern design, a covered entrance, and landscaped areas.

A spacious lobby with a reception desk, a blue decorative wall, and a wooden floor.

A hotel lobby with a reception desk, seating area, and large windows.

A hotel lobby with a seating area, a bar, and a TV screen.

13. Fairfield Inn & Suites Springfield Holyoke

Holyoke

MONA

฿4,393

฿4,907 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

A modern interior with a large window, a wooden table, and bar stools.

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

14. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Augusta

฿4,015

฿4,484 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio with white chairs and tables, a central fire feature, and string lights.

A hotel with a sign reading "D. HOTEL & SUITES" on the facade.

A hotel room with a striped sofa, a bed with a decorative headboard, a large wall painting, and a sunburst light fixture.

A bedroom with a four-poster bed, a leather sofa, a wooden coffee table, and a view of greenery through the window.

15. D. Hotel Suites & Spa

Holyoke

Patricia

฿4,082

฿4,776 total

includes taxes & fees

4 Nov - 5 Nov

An indoor swimming pool with blue walls, large windows, and several lounge chairs.

A modern hotel lobby with a dining area, seating, and a TV screen on the wall.

A Hampton Inn hotel with a modern design, featuring a large entrance, a well-lit parking area, and multiple flags.

A snack display with various packaged foods and a microwave.

16. Hampton Inn Chicopee/Springfield

Chicopee

Melissa

฿3,890

฿4,413 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio area with seating, a fire feature, and a view of the building's exterior.

A hotel room with two beds, a large window with a view of trees, and a wall mural.

A modern bar area with a long counter, multiple screens, and a seating area with metal chairs.

A modern bar area with a long counter, multiple bar stools, and a wooden accent wall.

17. Courtyard by Marriott West Springfield

West Springfield

Amy

฿4,401

฿5,036 total

includes taxes & fees

1 Nov - 2 Nov

A patio area with a stone fire pit, wicker furniture, and a view of the building's interior.

A spacious lobby with comfortable seating, a fireplace, and large windows.

A spacious hotel lobby with a high ceiling, a fireplace, seating areas, and a large TV screen.

A hotel exterior with a sign reading "Residence Inn Marriott."

18. Residence Inn Springfield Chicopee

Chicopee

Ronald

฿5,677

฿6,440 total

includes taxes & fees

18 Oct - 19 Oct

A laundry room with white appliances, green stools, and a colorful artwork on the wall.

An outdoor patio with a barbecue grill, seating area, and pergola.

A hotel room with a bed, two bedside tables with lamps, a nightstand, and a carpeted floor.

A conference room with a rectangular table surrounded by chairs, large windows with curtains, and a patterned carpet.

19. Homewood Suites by Hilton Holyoke-Springfield/North

Holyoke

Andrew

฿5,137

฿5,738 total

includes taxes & fees

25 Oct - 26 Oct

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."

A cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.

A hallway with a collection of plates on the walls, leading to a staircase.

20. The Porches Inn at Mass MoCA

North Adams

Ram

฿5,563

฿6,966 total

includes taxes & fees

4 Nov - 5 Nov

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Holiday Rentals in Western Massachusetts

Aparthotel

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

A spacious living room with large windows, a fireplace, and a variety of seating options.

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

Vacation Village in the Berkshires

Williamstown

"Very pleased with our stay -great place for the family we will G-d willing return"

Aparthotel

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.

Berkshire Mountain Lodge

Pittsfield

"Our visit was very nice. Facilities were beautiful!"

Aparthotel

A large, multi-story house with a reflective pond in front, surrounded by stone walls and trees.

A stone bench by a calm lake with a stone wall and grass in the foreground.

A serene pond with a stone bridge, surrounded by lush greenery and a house in the background.

The Ponds at Foxhollow

Lenox

"Quiet property. Convenient location."

Cottage

A wooden deck with outdoor seating and a view of a forest.

A cozy dining area with a round table, chairs, and a hanging light fixture.

A cozy attic room with a sloped ceiling, wooden beams, a ceiling fan, and a large window with a view of the outdoors.

A wooden cabin with a balcony, surrounded by a stone wall and a forest.

A-frame Cabin w/ Furnished Deck in Becket!

Becket

"This cabin has absolutely everything you can think of!! Shampoo, conditioner, pots and pans, cutlery, towels, bug spray, firewood, fans, AC, even a car charger!! I was a little worried because I didn’t connect with the property manager but I had received all the check in information I needed. Absolutely no worries needed! Check in and check out was totally seamless."

Cottage

A dining area with a wooden table, white chairs, a brick column, a vase with sunflowers, and a basket with bread and tomatoes.

A kitchen with a wooden island, a brick wall, a vintage stove, and a large wooden door.

A two-story house with a front porch, a brick chimney, and a well-maintained garden.

An outdoor dining area with a wooden table and white chairs, surrounded by lush greenery and trees.

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Lee

"What a charming home! The bathrooms and bedrooms were updated beautifully. The downstairs was updated enough while keeping the character."

Apartment

A lakeside view with a red building, trees, and a calm lake.

A spacious kitchen with a large oven and a dining area with a round table and chairs.

A compact kitchen with a refrigerator, microwave, and sink. There is a dining table with chairs and a vase of flowers. The room has wooden beams on the ceiling and a ceiling fan.

A two-story house with a deck overlooking a lake, surrounded by trees and a small fenced area.

Lakefront Orange Vacation Rental - Pet Friendly!

Orange

"Lovely, very clean, and well appointed. Host was amazing, 2 rocking chairs on front stoop overlooking the water was beautiful, peaceful.The interiorand decor was beautiful and very comfortable. We used our kayaks, which was great. It is an in̈cline downhill to carry your kayak. "

Cottage

A rustic wooden cabin with a porch, a bench, and a chair.

A spacious living room with a ceiling fan, a sofa, a coffee table, and a dining area with chairs and a table.

A dining area with a table and chairs, large windows, and a hanging light fixture.

A kitchen with wooden cabinets, a stove, a microwave, and a refrigerator. There is a window with a curtain and a door leading to another room.

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Charlemont

"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "

Cottage

A spacious living room with a fireplace, leather sofas, a coffee table, and a dining area with a table and chairs.

A sign for Balderdash Cellars with a wooden fence, a tree, and a parking lot in the background.

A rustic wooden interior with a counter displaying various items, a sign for 'MERLOT', and a view of the outdoors.

A modern kitchen with light grey cabinets, stainless steel appliances, and a large window providing a view of greenery.

3 Acres, Mtn Views, Hot Tub, Steps to Winery

Richmond

"This home is exceptional in all respects --beautifully situated on lovely property, well located in southern Berkshires. Newly remodeled. Great outdoor space. Fabulous kitchen with new appliances, extremely well-outfitted. Host easily accessible. Exceeded all expectations. Would definitely return if plans allow."

Cottage

A wooden deck with outdoor furniture and a red umbrella, overlooking a grassy yard and a forested hill.

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

A cozy living room with a fireplace, leather sofas, and a wooden interior.

A living room with a blue sofa, a wooden coffee table, a fan, and a patterned rug.

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Charlemont

"Loved this old home! Record player and records were fun to listen to. Pickle ball across the street was excellent! Well stocked kitchen great for cooking in. I had a tough time with water pressure and temperature but it could have been user error. Beds were comfortable except for the twin, which was a bit too firm! Would definitely rent here again "

Cottage

A spacious living room with exposed wooden beams, a fireplace, and comfortable seating.

A dining area with a wooden table and chairs, a chandelier, and a view of the outdoors through a window.

A two-story house with a large tree in front, surrounded by lush greenery.

A wooden deck with a stone wall, a grill, and outdoor furniture.

Charlemont Retreat on Chickley River w/ EV Charger

Charlemont

"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...

Apartment

A two-story house with a stone patio, outdoor seating, and a grill.

A small, rustic cabin with a stone foundation and a wooden structure covered in climbing vines.

A spacious living room with a blue sofa, a red armchair, and a wooden dining table.

A single-story house with a sloped roof, a front door, and a small porch area.

Vacation Rental Home in the Berkshires!

Williamstown

"This little guest house is a gem. Charming, comfortable and with a location that can’t be beat as a base for touring the northern Berkshires and southern Vermont. Everything was in good order, check-in was easy, and the place is well equipped with kitchen essentials. The views are gorgeous. "

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Stay near popular Western Massachusetts attractions

A forested hillside with a clear path and a small building at the top.

Jiminy Peak Mountain Resort

8.8/10 (311 reviews)

Southern New England's largest ski resort transforms into a summer playground with thrilling attractions. Glide down 45 winter trails or ride the Mountain Coaster through Berkshire Mountain scenery.

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A roller coaster at an amusement park with a clear sky.

Six Flags New England

8.4/10 (599 reviews)

New England's largest amusement park thrills with 11 roller coasters, including the top-rated Superman The Ride. Experience heart-pounding drops on Wicked Cyclone, or cool off at Hurricane Harbour water park.

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A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 reviews)

Tanglewood enchants as the summer home of the Boston Symphony Orchestra, set in the picturesque Berkshire Hills. Enjoy world-class performances while picnicking on the expansive lawns as the sun sets over the mountains.

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A basketball court with spectators, a scoreboard, and a wall of portraits.

Naismith Memorial Basketball Hall of Fame

8.6/10 (481 reviews)

The Basketball Hall of Fame celebrates the sport's greatest legends in Springfield, basketball's birthplace. Explore interactive exhibits, test your skills on Centre Court, and immerse yourself in the game's rich history.

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A snowy cityscape with various buildings and a large sports stadium.

Amherst College

9.2/10 (300 reviews)

Explore Amherst College's historic College Row and impressive art and natural history museums. Wander through the tranquil Yushien Japanese Garden or attend one of the many public cultural events on campus.

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A food court with various food stalls, including one for batter fried cheese curds and another for popcorn.

Eastern States Exposition

8.4/10 (260 reviews)

New England's largest fair, The Big E draws 1.6 million visitors annually with agricultural exhibits and entertainment. Explore the Avenue of States and Storrowton Village while sampling diverse regional cuisine.

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A historic building with ivy-covered brick walls, a large lawn, and a clear blue sky.

Williams College

9.4/10 (534 reviews)

Williams College offers a prestigious liberal arts education amid the scenic Berkshire Mountains. Visitors can explore the renowned Williams College Museum of Art and attend public lectures in this intellectual haven.

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Eastern States Exposition

8.6/10 (302 reviews)

This beloved New England fair showcases all six states' cultures through exhibits, food, and entertainment. Explore the Avenue of States, sample iconic cream puffs, or catch a live concert during its September run.

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Learn more about Western Massachusetts

Rolling hills and charming towns define this picturesque region, where art lovers flock to MASS MoCA in North Adams. Outdoor enthusiasts can hike Mount Greylock, while history buffs explore Norman Rockwell's studio in Stockbridge.

See all hotels in Western Massachusetts

A panoramic view of a valley with autumn foliage, a town in the distance, and rolling hills.

Top Western Massachusetts Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent

"Great staff,Spotless facility decent price"

Berkshire Mountain Lodge

8/10 Good

"Loved our stay. Room was nice and clean. Some things a little dated but great for the price!"

Holiday Inn Express Springfield Downtown by IHG

8/10 Good

"The room was clean and comfortable"

MGM Springfield

10/10 Excellent

"Clean"

Vacation Village in the Berkshires

10/10 Excellent

"Love the fireplace in our room! The amenities always make this place worth the money, and the views to top it all off!!"

Hotel UMass

8/10 Good

"Excellent"

Hotel On North

10/10 Excellent

"Beautiful boutique hotel. We will be back!"

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"I would recommend for families or large groups."

The Red Lion Inn

10/10 Excellent

"Great staff, heated bathroom floors."

More cheap stays in Western Massachusetts

Quality Inn Great Barrington

372 Main Street Great Barrington MA

฿2,562

฿2,861 total

1 Nov - 2 Nov

includes taxes & fees

8.6/10 Excellent! (1,004 reviews)

Quality Inn West Springfield

1150 Riverdale St West Springfield MA

฿2,954

฿3,381 total

2 Nov - 3 Nov

includes taxes & fees

7.2/10 Good! (1,012 reviews)

Holiday Inn Express Springfield Downtown by IHG

145 State Street Springfield MA

฿3,353

฿3,803 total

3 Nov - 4 Nov

includes taxes & fees

9/10 Wonderful! (1,323 reviews)

Hotel UMass

1 Campus Center Way Amherst MA

฿3,695

฿4,174 total

7 Oct - 8 Oct

includes taxes & fees

9/10 Wonderful! (1,014 reviews)

Comfort Inn & Suites Hadley - Amherst

400 Russell St Hadley MA

฿3,945

฿4,406 total

4 Nov - 5 Nov

includes taxes & fees

9.2/10 Wonderful! (1,008 reviews)

Hampton Inn West Springfield

1011 Riverdale St West Springfield MA

฿4,100

฿4,693 total

1 Nov - 2 Nov

includes taxes & fees

Explore a world of travel with Expedia

More ways to book

Book Hotels in Western Massachusetts on Expedia.com

Find hotels in Western Massachusetts, MA from ฿2,861

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Western Massachusetts

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Western Massachusetts hotels

1. Homewood Suites by Hilton Hadley Amherst

2. Comfort Inn & Suites Hadley - Amherst

3. Fairfield Inn & Suites Springfield Northampton/Amherst

4. Hotel UMass

5. Hotel Northampton

6. Inn on Boltwood

7. Courtyard by Marriott Hadley Amherst

8. The Yankee Inn

9. Tru by Hilton Chicopee Springfield

10. The Ellery

11. The Williams Inn

12. MGM Springfield

13. Fairfield Inn & Suites Springfield Holyoke

14. Hotel Downstreet, an Ascend Collection Hotel

15. D. Hotel Suites & Spa

16. Hampton Inn Chicopee/Springfield

17. Courtyard by Marriott West Springfield

18. Residence Inn Springfield Chicopee

19. Homewood Suites by Hilton Holyoke-Springfield/North

20. The Porches Inn at Mass MoCA

Holiday Rentals in Western Massachusetts

Vacation Village in the Berkshires

Berkshire Mountain Lodge

The Ponds at Foxhollow

A-frame Cabin w/ Furnished Deck in Becket!

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Lakefront Orange Vacation Rental - Pet Friendly!

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3 Acres, Mtn Views, Hot Tub, Steps to Winery

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Charlemont Retreat on Chickley River w/ EV Charger

Vacation Rental Home in the Berkshires!

Stay near popular Western Massachusetts attractions

Jiminy Peak Mountain Resort

Six Flags New England

Tanglewood Music Center

Naismith Memorial Basketball Hall of Fame

Amherst College

Eastern States Exposition

Williams College

Eastern States Exposition

Learn more about Western Massachusetts

Top Western Massachusetts Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

Berkshire Mountain Lodge

Holiday Inn Express Springfield Downtown by IHG

MGM Springfield

Vacation Village in the Berkshires

Hotel UMass

Hotel On North

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Red Lion Inn

More cheap stays in Western Massachusetts

Quality Inn Great Barrington

Quality Inn West Springfield

Holiday Inn Express Springfield Downtown by IHG

Hotel UMass

Comfort Inn & Suites Hadley - Amherst

Hampton Inn West Springfield

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