Title: Middlefield Vacation Rentals from CA $174: Short-Term Rentals for 2026 | Expedia.ca

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![Beautiful every time of the year ](https://images.trvl-media.com/place/132966/c928e3a4-90c5-4fe2-b9e6-d63b3da86513.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Elizabeth Massa Peroulakis

![](https://images.trvl-media.com/place/132966/c928e3a4-90c5-4fe2-b9e6-d63b3da86513.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=132966&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=132966&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=132966&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=132966&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Middlefield vacation rentals

![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/9e460e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/8168a5fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Village in the Berkshires

[](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

Williamstown

8.8/10

Excellent

(2,229 reviews)

"I great place to stay!!"

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Maricel

CA $142

CA $174 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/3f592f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/b35035ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jiminy Peak Mountain Resort

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

Hancock

8.2/10

Very good

(989 reviews)

"nice and clean, good customer service, but the room is smell. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Huang

CA $259

CA $289 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow | Living area](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/1e2d02da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/a965b40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/65ba1b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Huttopia Berkshires 

[](https://www.expedia.ca/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

Williamstown

9.4/10

Exceptional

(8 reviews)

"Healthy food too!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

GEORGINA

CA $230

CA $257 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/4626de59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/e3cded0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/08d859c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/e43c1750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Creation Station is a cozy place so make yourself at home.

[](https://www.expedia.ca/Easthampton-Hotels-The-Creation-Station-Is-A-Cozy-Place-So-Make-Yourself-At-Home.h34080135.Hotel-Information)

Easthampton Ma.

10/10

Exceptional

(73 reviews)

"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Connie P.

CA $246

CA $383 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Easthampton-Hotels-The-Creation-Station-Is-A-Cozy-Place-So-Make-Yourself-At-Home.h34080135.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/ded0f208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/6065c0a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/33f72fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/f2798a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Button's Modern Luxury Walkup Downtown Northampton

[](https://www.expedia.ca/Northampton-Hotels-Buttons-Modern-Luxury-Walkup-Downtown-Northampton.h117659835.Hotel-Information)

Northampton

10/10

Exceptional

(2 reviews)

"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

AMY

CA $450

CA $832 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Northampton-Hotels-Buttons-Modern-Luxury-Walkup-Downtown-Northampton.h117659835.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/79e104d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/a233230f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/7a56f82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/ed6f8836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Valley View Post & Beam Villa!

[](https://www.expedia.ca/South-Deerfield-Hotels-Cozy-Valley-View-Post-Beam-Villa.h92050515.Hotel-Information)

Whately

10/10

Exceptional

(8 reviews)

"Thanks for a great stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrea M.

CA $821

CA $1,048 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/South-Deerfield-Hotels-Cozy-Valley-View-Post-Beam-Villa.h92050515.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/7377fc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/2350af4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/f63afa55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/0f27818f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Big farmhouse in the foothills of the Berkshires

[](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information)

Russell

10/10

Exceptional

(143 reviews)

"Perfect spot for a family celebration!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kerry P.

CA $246

CA $470 total

includes taxes & fees

Feb 13 - Feb 14

[](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/f305b62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/597105fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/037efde9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/38972098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Riverbend Berkshire East Basecamp - 3 bedrooms available

[](https://www.expedia.ca/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information)

Charlemont

10/10

Exceptional

(2 reviews)

"Very nice house and the stay was unproblematic!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Noah K.

CA $219

CA $582 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/dba15cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/2281e60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/4e64ac0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/af01e53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information)

Sherwood Forest

9.8/10

Exceptional

(11 reviews)

"My wife and I wanted a quick get away in the Berkshires with our dog and this property couldn't have been more perfect. The house was wonderful, clean, cozy, and had everything we needed from towels, to kitchen utensils and appliances, to smart TVs. The location is set back in the woods in an already very quiet town, giving plenty of peace, quiet, and privacy. The hot tub was the highlight of the stay. The host is excellent with communication and was eager to be of assistance if needed. We...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Zack D.

CA $219

CA $540 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/9f36ff80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/fc000043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/8d6ee530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/9751d742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat

[](https://www.expedia.ca/Charlemont-Hotels-1920s-Inspired-Spacious-5-Bedroom-Home-Minutes-To-Berkshire-East.h122227227.Hotel-Information)

Charlemont

10/10

Exceptional

(2 reviews)

"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jason F.

CA $353

CA $889 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Charlemont-Hotels-1920s-Inspired-Spacious-5-Bedroom-Home-Minutes-To-Berkshire-East.h122227227.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/w4000h2662x0y5-f1ed56ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/4fb8018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/7d4bb1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/669a10ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

[](https://www.expedia.ca/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information)

Hinsdale

9.8/10

Exceptional

(36 reviews)

"Amazing, peaceful, immaculately clean property. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cec C.

CA $354

CA $744 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/dcb799f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/6137aab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home in Great Barrington

[](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information)

Great Barrington

9.8/10

Exceptional

(27 reviews)

"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cameron M.

CA $220

CA $368 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/ec2d4d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/w1008h683x16y0-6785a02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/cbafac8b_edited_20ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/0789534a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

[](https://www.expedia.ca/Hancock-Hotels-Mountain-Getaway-Suite-Ski-OnOff-Jiminy-Peak-Fully-Redone-Decor.h124014382.Hotel-Information)

Hancock

10/10

Exceptional

(2 reviews)

"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeffrey R.

CA $187

CA $377 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Hancock-Hotels-Mountain-Getaway-Suite-Ski-OnOff-Jiminy-Peak-Fully-Redone-Decor.h124014382.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/c64df1b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/a0875211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/edf0cab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/4b9dab09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Penthouse Apartment on Park Street

[](https://www.expedia.ca/Adams-Hotels-Penthouse-Apartment-On-Park-Street.h122136838.Hotel-Information)

Adams

9.6/10

Exceptional

(14 reviews)

"Clean property, easy check in, and the owner was super communicative. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amanda W.

CA $198

CA $383 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Adams-Hotels-Penthouse-Apartment-On-Park-Street.h122136838.Hotel-Information)

![TV, fireplace, books](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/3201c410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/74649c70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/ff859ff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/ba39107a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike

[](https://www.expedia.ca/Charlemont-Hotels-Joia-Verde-ChaletSleeps-8.h123354233.Hotel-Information)

Charlemont

CA $438

CA $1,083 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Charlemont-Hotels-Joia-Verde-ChaletSleeps-8.h123354233.Hotel-Information)

![TV, fireplace, DVD player, offices](https://images.trvl-media.com/lodging/120000000/119240000/119237000/119236971/0ca83843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119240000/119237000/119236971/a71c2fa9_edited_793c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119240000/119237000/119236971/478690d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/120000000/119240000/119237000/119236971/a294f9a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

[](https://www.expedia.ca/Hancock-Hotels-Luxury-Jiminy-Ski-On-Off-Village-Ctr-Condo-Sleeps4.h119236971.Hotel-Information)

Hancock

10/10

Exceptional

(3 reviews)

"Excellent instructions by the owner for the check in process, which was easy. The room was beautiful and very clean, and exactly as advertised. We would absolutely recommend and stay again!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chad J.

CA $178

CA $384 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Hancock-Hotels-Luxury-Jiminy-Ski-On-Off-Village-Ctr-Condo-Sleeps4.h119236971.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/cd1323be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/25e02c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/621adf1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/d3c8327e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun Filled Lenox Retreat - Minutes to Tanglewood!

[](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information)

Lee

9.6/10

Exceptional

(4 reviews)

"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah D.

CA $247

CA $628 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/3bd0d6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/c34ecca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/399488d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/8b16599a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sweet Cozy Victorian in Housatonic. Close to everything. 

[](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information)

Housatonic

10/10

Exceptional

(3 reviews)

"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cheryl F.

CA $185

CA $365 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/8de4c71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/6b5af50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/06261f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/43b40eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Near Tanglewood: Historic Summer Retreat

[](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information)

New Lebanon

9.4/10

Exceptional

(26 reviews)

"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paul S.

CA $148

CA $461 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information)

![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/8d87241a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/d712468a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/64f95c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/87b97def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Great Barrington Get Away

[](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information)

Great Barrington

9.4/10

Exceptional

(26 reviews)

"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Deb W.

CA $390

CA $716 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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## Find vacation rentals that suit your style

Private vacation homes

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Villas

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Apartments

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Condos

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Middlefield%2C+Massachusetts%2C+United+States+of+America&regionId=132966&latLong=42.348419%2C-73.015099&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Middlefield%2C+Massachusetts%2C+United+States+of+America&regionId=132966&latLong=42.348419%2C-73.015099&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CABIN)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Middlefield%2C+Massachusetts%2C+United+States+of+America&regionId=132966&latLong=42.348419%2C-73.015099&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CHALET)

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## Top Middlefield Hotel Reviews

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay."

[](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg)

### Vacation Village in the Berkshires

10/10 Excellent

"Spacious 2 bed 2 bath!"

[](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg)

### Berkshires Untold

10/10 Excellent

"loved "

[](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

![Fairfield Inn & Suites Springfield Northampton/Amherst](https://images.trvl-media.com/lodging/9000000/8450000/8449800/8449737/e6abed3c_y.jpg)

### Fairfield Inn & Suites Springfield Northampton/Amherst

10/10 Excellent

"Gorgeous room amazing stay"

[](https://expedia.ca/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-NorthamptonAmherst.h8449737.Hotel-Information)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"We had a lovely extended family weekend here. The staff was outstanding, every staff member was helpful, friendly and courteous. The large room in back of the lobby was especially helpful for our large group to hang out in and be comfortable. Everyone enjoyed the pool and hot tub despite it being so cold out. The hotel is well maintained. The only small complaint I had was that the bathroom in our room needs to be refreshed. We have already started talking about coming back in the warmer weather to enjoy some of the outdoor activities in in the area."

[](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

![Quality Inn & Suites Northampton - Amherst](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/f86e1269_y.jpg)

### Quality Inn & Suites Northampton - Amherst

10/10 Excellent

"Great room, very clean and welcoming, helpful staff. Breakfast was pretty good too!"

[](https://expedia.ca/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.Hotel-Information)

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Great clean room. Staff great. Breakfast and selection great! "

[](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

![Hotel Northampton](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/fe4b5272_y.jpg)

### Hotel Northampton

10/10 Excellent

"The staff were amazing and the room was perfect. "

[](https://expedia.ca/Springfield-Hotels-Hotel-Northampton.h17876.Hotel-Information)

![The Ellery](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/0b76727c_y.jpg)

### The Ellery

10/10 Excellent

"Comfortable room, great breakfast with cozy fireplace. Friendly and efficient staff. Easy parking. Walkable area amidst Smith College and fifteen minute walk to downtown Northampton attractions and restaurants. "

[](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.Hotel-Information)

## Find out more about Middlefield

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlefield. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Middlefield ](https://expedia.ca/Middlefield-Private-Vacation-Homes.d132966-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Condo Rentals in Middlefield ](https://expedia.ca/Middlefield-Condos.d132966-aaCondos.Travel-Guide-Accommodation)
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- [Motels in Middlefield ](https://expedia.ca/Middlefield-Motels.d132966-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Middlefield ](https://expedia.ca/Middlefield-Cabins.d132966-aaCabins.Travel-Guide-Accommodation)
- [Guest Houses in Middlefield ](https://expedia.ca/Middlefield-Guest-Houses.d132966-aaGuestHouses.Travel-Guide-Accommodation)
- [Chalets in Middlefield ](https://expedia.ca/Middlefield-Chalets.d132966-aaChalets.Travel-Guide-Accommodation)
- [Inns in Middlefield ](https://expedia.ca/Middlefield-Inns.d132966-aaInns.Travel-Guide-Accommodation)
- [Aparthotels in Middlefield ](https://expedia.ca/Middlefield-Apart-Hotels.d132966-aaApartHotels.Travel-Guide-Accommodation)
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- [Lodges in Middlefield ](https://expedia.ca/Middlefield-Lodges.d132966-aaLodges.Travel-Guide-Accommodation)
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## Frequently asked questions

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### What are some of the best vacation home rentals in Middlefield?

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