Title: Middlefield Vacation Rentals from CA $176: 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

# Middlefield Vacation Rentals

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## Check prices for these dates

Tonight

[Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=132966&startDate=2025-12-09&endDate=2025-12-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=132966&startDate=2025-12-10&endDate=2025-12-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=132966&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=132966&startDate=2025-12-19&endDate=2025-12-21&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

![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining room](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/16150550.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)

![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Village in the Berkshires

Williamstown

8.8/10

Excellent

(2168)

"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"

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

Karla

CA $144

CA $176 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 | Private kitchen](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/2d5c8478.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/bc7f49dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/fd380371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Huttopia Berkshires 

Williamstown

10/10

Exceptional

(7)

"Perfect place for a relaxing getaway! We loved everything! "

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

Cammie

CA $236

CA $263 total

includes taxes & fees

Dec 14 - Dec 15

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

![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/ebd04e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f251fc45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Ponds at Foxhollow

Lenox

8.6/10

Excellent

(136)

"A good place for vacation that you can enjoy and rest. Very nice and safe place."

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

Cyril

[](https://www.expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830.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)

![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/9c53d20e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 Bedroom Condo 1/2 mile from base | In-room dining](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/40940c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jiminy Peak Mountain Resort

Hancock

8.2/10

Very good

(987)

"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 $262

CA $292 total

includes taxes & fees

Dec 10 - Dec 11

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

![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/406cc767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, eco-friendly cleaning products](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/780d89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/59edf6fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pet Friendly Riverfront Home in Great Barrington

Great Barrington

9.4/10

Exceptional

(6)

CA $280

CA $412 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/afd0b229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/2598e461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/f26456ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/bc016b9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peace and quiet on the lake

Sherwood Forest

9.6/10

Exceptional

(230)

"Great communication, comfortable home, love the location"

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

Susan C.

[](https://www.expedia.ca/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/5bf808fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/d7946d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/aa306e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/92ba9b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Kemble- Built by a US Secretary of State in Lenox

Lenox

10/10

Exceptional

(17)

"Perfect house for our family reunion. Everything was perfect."

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

Michael C.

[](https://www.expedia.ca/Lenox-Hotels-The-Kemble-Built-By-A-US-Secretary-Of-State-In-Lenox.h76003386.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/58b0972d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/d06b32cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/636f9a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/8b34823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 5-bedroom house in charming Lee with WiFi

Lee

8.0/10

Very good

(1)

"House was large, clean, and comfortable. "

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

John Z.

CA $530

CA $1,030 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information)

![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/be941bed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![7 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/9e7f1a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/4ebdefe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/d795e81b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington

10/10

Exceptional

(28)

"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "

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

Johnathan B.

[](https://www.expedia.ca/Great-Barrington-Hotels-Minutes-From-Ski-Butternut.h78701034.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121220000/121211000/121210927/486f914e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121211000/121210927/b5fe1e13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121220000/121211000/121210927/c2e5501a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121220000/121211000/121210927/83beab49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Experience Three Sisters Sanctuary in Goshen, MA

Goshen

10/10

Exceptional

(2)

"We had such a great time staying here as always. "

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

David F.

[](https://www.expedia.ca/Goshen-Hotels-Experience-Three-Sisters-Sanctuary-In-Goshen.h121210927.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96240000/96232500/96232485/2573bb0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96240000/96232500/96232485/039badcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96240000/96232500/96232485/b765881e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/97000000/96240000/96232500/96232485/92c47af4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. 

Hinsdale

9.8/10

Exceptional

(19)

"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"

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

maria f.

[](https://www.expedia.ca/Hinsdale-Hotels-Berkshire-Ashmere-Lake-Lodging-Quiet-Room.h96232485.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/18066543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/dcf5df54_edited_d00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/e43d10e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/f076ba69_edited_5004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfortable Berkshires retreat on mtn resort, SISO

Hancock

9.0/10

Wonderful

(7)

"Kind and responsive host."

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

Javier

CA $446

CA $1,015 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Hancock-Hotels-Comfortable-Berkshires-Retreat-On-Mtn-Resort.h109434975.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/63595554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/7d7a19ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/62b3ce52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/35eff0e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge

10/10

Exceptional

(135)

"Clean house, well appointed, great location, responsive owner"

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

sara m.

[](https://www.expedia.ca/West-Stockbridge-Hotels-Location-Location-Berkshire-Glamour.h33932760.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/02c7301e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/e175fcb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/b2d17216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/960bf7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amore Estate - beautiful room with many places to explore and relax in.

Lenox

9.2/10

Wonderful

(33)

"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."

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

Jacquie S.

[](https://www.expedia.ca/Lenox-Hotels-October-Mountain-Escape.h91593496.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/70000000/69740000/69737600/69737532/f418f910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/70000000/69740000/69737600/69737532/5d175d8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/70000000/69740000/69737600/69737532/7d7c96e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/70000000/69740000/69737600/69737532/866c485c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Great Escape Ski Cottage w/HOT TUB @ Great Barrington 

Great Barrington

10/10

Exceptional

(53)

"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."

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

Carol R.

[](https://www.expedia.ca/Great-Barrington-Hotels-The-Great-Escape-Ski-Cottage-WHOT-TUB-Great-Barrington.h69737532.Hotel-Information)

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

![Smart TV, books, music library, video library](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/d59ece13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/73d09dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/c74cafb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Easthampton Ma.

10/10

Exceptional

(72)

"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 $249

CA $373 total

includes taxes & fees

Jan 6 - Jan 7, 2026

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

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/ecdea449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/4bbc4f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/162d61f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest

10/10

Exceptional

(5)

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

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

Sharon K.

CA $202

CA $523 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/5d0aa061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/ed3ffaa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/w1440h1084x0y1-9f76bc91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c8837e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hancock Village Inn Near Jiminy Peak

Hancock

10/10

Exceptional

(16)

"Amazing Inn. Cozy and everything we needed. "

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

Price F.

CA $816

CA $1,522 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/a5ddb496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/7e362400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/63cb703a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/89102e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield

9.8/10

Exceptional

(150)

"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."

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

Sarah A.

[](https://www.expedia.ca/Pittsfield-Hotels-Beautiful-8-Bedroom.h33492239.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/20000000/20000000/19992400/19992324/18f8b7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/20000000/20000000/19992400/19992324/1a566e6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/20000000/20000000/19992400/19992324/709f9f9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/20000000/19992400/19992324/bdc9a74c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lee

9.4/10

Exceptional

(71)

"Wonderful time !! Location was perfect and we really enjoyed our time here "

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

Sue P.

[](https://www.expedia.ca/Lee-Hotels-Elegant-19th-Century-New-England-Newly-Renovated-1BR-Vacation-Rental.h19992324.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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## Top Middlefield Hotel Reviews

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg)

### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"Excellent stay, nice, clean 2 bedroom Villa, staff excellent, amenities excellent, great location would definitely stay again "

[](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg)

### Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Great staff especially Katherine "

[](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

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

### The Ellery

10/10 Excellent

"Breakfast could be improved. Homemade muffins, fresh croissant, etc. "

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

![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg)

### Hotel On North

10/10 Excellent

"Spacious rooms. Attentive staff. Free parking behind the hotel."

[](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information)

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"It was all well cared for."

[](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

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

### Berkshire Mountain Lodge

10/10 Excellent

"I am a cross country traveling nurse. The Berkshire Mountain Lodge was perfect for my needs. A fully functioning well appointed kitchen. Spacious living quarters with excellent views. The best water pressure on a shower that I have ever known. Fantastic after a long day of work or out hiking the many nature trails here. And the bed was so perfectly firm and cozy that I drifted effortlessly to sleep. The grounds, the amenities and the coordinated activities to bring you together in community made me feel included. Definitely a place I will continue to return to for many years."

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

"The staff was very friendly, and the hotel room was basically a small condo. The overall experience was heavenly."

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

![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 room was spacious and clean, the jetted tub was a nice treat, and the breakfast was fresh. "

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

"I first visited here 9 years ago for one night only and told myself I’d have to come back, which I did this year for an entire week. The hotel itself was lovely (great breakfast options, clean, affordable, attentive staff) and Northampton has now become one of my favorite cities. So much to do and see!"

[](https://expedia.ca/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.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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## Frequently asked questions

### Are there vacation rentals in Middlefield?

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

### What’s there to see and do in Middlefield?

### What’s a vacation rental in Middlefield like?

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