Title: Sheffield Vacation Rentals from CA $304: Short-Term Rentals for 2025 | Expedia.ca

 

[Hotels in Sheffield](https://expedia.ca/Sheffield-Hotels.d157238.Travel-Guide-Hotels)[Flights to Sheffield](https://expedia.ca/Cheap-Flights-To-Sheffield.d157238.Travel-Guide-Flights)[Sheffield Car Rentals](https://expedia.ca/Car-Rentals-In-Sheffield.d157238.Car-Rental-Guide)[Sheffield Vacation Packages](https://expedia.ca/Sheffield.d157238.Destination-Travel-Guides)

![](https://mediaim.expedia.com/destination/1/0c91d6ccb27784bad8a181efd70e605a.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Sheffield Vacation Rentals

-   ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)
    
    ### 
    
    Change your mind
    
    Book hotels with free cancellation
    
-   ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)
    
    ### 
    
    Treat yourself
    
    Sign in to save 10% or more on thousands of hotels
    
    [Sign in](https://www.expedia.ca/login)
    
-   ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)
    
    ### 
    
    Be picky
    
    Search almost a million properties worldwide
    

## Check prices for these dates

Tonight

[Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Sheffield

![Dining](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/9fa6f837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/edf60411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/13f82703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/eca50f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

10/10

Exceptional

(9)

"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "

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

Robert B.

CA $546

CA $966 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/46c8a41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/7d583158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/751b9826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/f9623fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Antique Farmhouse Totally Restored

Sheffield

9.8/10

Exceptional

(93)

"Enjoyed the property, location and charming house that was well stocked with everything we needed."

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

Sharon S.

[](https://www.expedia.ca/Sheffield-Hotels-Antique-Farmhouse-Totally-Restored.h27129515.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)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/ebd04e74.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)

![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

(132)

"Perfect location "

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

krystle

CA $272

CA $304 total

includes taxes & fees

Nov 21 - Nov 22

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

![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)

![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.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)

### Pet Friendly Riverfront Home in Great Barrington

Great Barrington

8.8/10

Excellent

(3)

"Close to a great bakery and near to a farm market and shopping mall. "

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

Cristine C.

CA $268

CA $396 total

includes taxes & fees

Nov 14 - Nov 15

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

![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)

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

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/eccd60b1.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

(132)

"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)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/5bf808fb.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)

![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)

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

Lenox

10/10

Exceptional

(17)

"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...

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

Carrie S.

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/a366bf74.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

(32)

"Beautiful property with tons of space and fantastic for a group of friends or family"

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

Greg S.

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

![Dining](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/f8fd77b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/2267bfa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/8b9796c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/b18d7fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Lee

9.6/10

Exceptional

(16)

"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"

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

Annie C.

[](https://www.expedia.ca/Lee-Hotels-Cordelia-By-AvantStay-Amazing-Backyard.h101271254.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)

![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/fb68a83f.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)

![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)

### 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 $595

CA $1,108 total

includes taxes & fees

Dec 1 - Dec 2

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

![Exterior](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547893/9b0a12c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547893/aa174362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547893/5f52ca5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547893/142c6abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Summer Lake Cottage, private beach, Berkshire Hills, small village

Lakeville

9.4/10

Exceptional

(84)

"Wonderful lake retreat 🥾"

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

Elizabeth B.

[](https://www.expedia.ca/Lakeville-Hotels-Summer-Lake-Cottage.h33547893.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/101470000/101469400/101469345/052d8e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101470000/101469400/101469345/04dddce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101470000/101469400/101469345/be2467fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101470000/101469400/101469345/ed51271f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Blue Elm - A Historic Berkshire Cottage

Sheffield

10/10

Exceptional

(12)

"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...

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

Marc R.

CA $252

CA $534 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Sheffield-Hotels-The-Blue-Elm-A-Historic-Berkshire-Cottage.h101469345.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/0f6c9404.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peace and quiet on the lake

Sherwood Forest

9.6/10

Exceptional

(227)

"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "

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

Anika J.

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

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

![TV, fireplace](https://images.trvl-media.com/lodging/20000000/20000000/19992400/19992324/57c3dcba.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

(69)

"We ran all over the Berkshires. Nice central location. "

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

Patrick M.

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

![Property grounds](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/22f66f00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/589cb0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/f9dd0939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/dd2937db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tranquil Lakeside Escape in the Berkshires

Lenox

10/10

Exceptional

(1)

"perfect location to go everywhere in the Berkshires"

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

Edward G.

[](https://www.expedia.ca/Lenox-Hotels-Tranquil-Lakeside-Escape-In-The-Berkshires.h116593874.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/4b89dca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/e427035e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/61b3f659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/w1024h683x0y1-30c5b99d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Island - Largest Fresh Water Reservoir in Mass

Otis

8.6/10

Excellent

(9)

"The house’s position on the water, being further out than all other surrounding homes, makes for beautiful views of the lake and all it activities. The sunrises are beautiful. Unfortunately when you don’t have proper running water and a toilet that flushes without having to put water in the tank almost every time, the experience is less than ideal. The host warned us of the toilet about 15 min before we arrived and never had the kitchen sink fixed in the 5 days we stayed. That was rather...

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

Colleen W.

[](https://www.expedia.ca/Otis-Hotels-Private-Island-On-Largest-Fresh-Water-Reservoir-In-Mass-Ski-Boat-Included.h67255071.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/20000000/19220000/19210700/19210630/4f0cf212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19220000/19210700/19210630/21d7f1c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19220000/19210700/19210630/71823c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19220000/19210700/19210630/22dc99a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Sherwood Forest

9.6/10

Exceptional

(229)

"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."

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

Donald G.

[](https://www.expedia.ca/Becket-Hotels-Quiet-Comfortable-Cabin-5-Min-Walk-To-Swimming-And-Boating.h19210630.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/120000000/119780000/119777200/119777182/832bba64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119780000/119777200/119777182/29d47a86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119780000/119777200/119777182/a13ca413.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119780000/119777200/119777182/8ad1be90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape

West Stockbridge

7.4/10

Good

(3)

"Beautiful quiet escape. Host was very prompt with answers to questions I had. Very nice re-model. I will definitely be back. "

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

Christopher W.

[](https://www.expedia.ca/West-Stockbridge-Hotels-Quiet-2BR1BA-Forest-View-Barn-Apartment-Newly-Renovated.h119777182.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78440000/78432200/78432175/56ecd142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78440000/78432200/78432175/ee760f47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78440000/78432200/78432175/1cc2075b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78440000/78432200/78432175/267faaac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.

Lee

10/10

Exceptional

(25)

"We had another great weekend stay with friends! Can’t say enough good things about the house and property and location"

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

Robin M.

[](https://www.expedia.ca/Lee-Hotels-Lakeview-Retreat-Mins-To-Downtown-Lenox.h78432175.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32820000/32817500/32817492/0e4f366e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32820000/32817500/32817492/4bd052c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32820000/32817500/32817492/4fbbd032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32820000/32817500/32817492/d149954d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Goshen Glass Chalet

Goshen

9.6/10

Exceptional

(41)

"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "

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

Tracy F.

[](https://www.expedia.ca/Goshen-Hotels-The-Goshen-Glass-Chalet.h32817492.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33120000/33119200/33119171/6ac2d2b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33120000/33119200/33119171/3f72fbe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33120000/33119200/33119171/043b4007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33120000/33119200/33119171/d1849562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

East Otis

10/10

Exceptional

(159)

"This was an exceptional spacious lake house with fantastic views of Otis reservoir! Clean clear water. You can walk down to the dock. We saw a bald eagle from the large deck. We were 9 adults, and we all had plenty of space with everything we needed! Lots of hiking spots nearby. "

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

Cyd S.

[](https://www.expedia.ca/Otis-Hotels-4br3bath-Lakefrontski-House-In-Berkshires-Fully-Fitted-Kitchen-Hi-Speed-Wifi.h33119171.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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-15&endDate=2025-11-16&regionId=157238&adults=2&sort=RECOMMENDED&openPlayBack=true)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

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

[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Vacation-Rentals.d157238.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Vacation-Rentals.d157238.Travel-Guide-VacationRentals)

## Top Sheffield Hotel Reviews

![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg)

### The Red Lion Inn

10/10 Excellent

"The Red Lion Hotel was a great place to stay!! I would definitley come back again and stay there! I loved the bar downstairs and the restaurant! Our room was perfect and we had lots of room! The bed was super comfy - a marshmallow bed!! LOL! The location was nice to walk to the different shops in town! Fun place! "

[](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information)

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

### Berkshires Untold

10/10 Excellent

"This property was great for our weekend getaway. It is conveniently located "

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

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

### Berkshire Mountain Lodge

10/10 Excellent

"Excellent all the way around"

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

![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg)

### Quality Inn

10/10 Excellent

"It was really nice staying here. The room was clean, bed was comfortable, and there was a mini-fridge that wasn't full of expensive drinks you're not supposed to touch! It was mostly quiet, except for the trains at night that pass behind the building. It is very close by to shops, cool architecture, and a nice walking path. Very safe area too. The breakfast wasn't the best, but it's free, and you can easily pop in to nearby restaurants if you want something better. The staff are very friendly and helpful. I would recommend staying here! It's a nice place to stay for the price."

[](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//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

"Very clean and roomy lodge (2 bedrooms); conveniently located; has kitchen; recreational facilities a bit dated. Will come back again. "

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

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

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

10/10 Excellent

"Excellent front desk staff. Ask for Steve. Very convenient to Monument Mountain and local ski resorts."

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

![Monument Mountain Motel](//images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg)

### Monument Mountain Motel

10/10 Excellent

"5 stars!"

[](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information)

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg)

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

10/10 Excellent

"View of the lake was lovely! Breakfast was fine—yogurt, eggs, pancakes and cereal. Coffee was plentiful!"

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

![Blackberry River Inn](//images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd_y.jpg)

### Blackberry River Inn

10/10 Excellent

"Charming place. No tv. Small room. Good breakfast. "

[](https://expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information)

## Find out more about Sheffield

**Everything you need to know about** **Sheffield** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sheffield vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sheffield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Sheffield vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Sheffield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sheffield vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sheffield vacation rentals we have selected for you start as low as CA $304 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Sheffield rentals**

At Expedia, we put the best Sheffield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sheffield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sheffield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sheffield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

-   Trending destinations on Expedia.ca
-   All accommodation types in Sheffield

### Trending destinations on Expedia.ca

-   [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals)
-   [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)
-   [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals)
-   [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals)
-   [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
-   [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals)
-   [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals)
-   [Palm Springs Vacation Rentals](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
-   [Tofino Vacation Rentals](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals)
-   [Calgary Vacation Rentals](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals)
-   [Costa Rica Vacation Rentals](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations)
-   [Vancouver Island Vacation Rentals](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals)
-   [Puerto Vallarta Vacation Rentals](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals)
-   [Hawaii Vacation Rentals](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
-   [Toronto Vacation Rentals](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals)
-   [Banff Vacation Rentals](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals)
-   [Penticton Vacation Rentals](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals)
-   [Osoyoos Vacation Rentals](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals)
-   [Mont Tremblant Vacation Rentals](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals)
-   [Big White Ski Resort Vacation Rentals](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals)
-   [Ontario Vacation Rentals](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
-   [British Columbia Vacation Rentals](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
-   [Prince Edward Island Vacation Rentals](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
-   [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

-   [Vacation Homes in Sheffield](https://expedia.ca/Sheffield-Private-Vacation-Homes.d157238-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Cottages in Sheffield](https://expedia.ca/Sheffield-Cottages.d157238-aaCottages.Travel-Guide-Accommodation)
-   [Apartments in Sheffield](https://expedia.ca/Sheffield-Apartments.d157238-aaApartments.Travel-Guide-Accommodation)
-   [B&B in Sheffield](https://expedia.ca/Sheffield-Bed-And-Breakfast.d157238-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Cabin Rentals in Sheffield](https://expedia.ca/Sheffield-Cabins.d157238-aaCabins.Travel-Guide-Accommodation)
-   [Farmstay in Sheffield](https://expedia.ca/Sheffield-Agritourism.d157238-aaAgritourism.Travel-Guide-Accommodation)
-   [Motels in Sheffield](https://expedia.ca/Sheffield-Motels.d157238-aaMotels.Travel-Guide-Accommodation)
-   [Condo Rentals in Sheffield](https://expedia.ca/Sheffield-Condos.d157238-aaCondos.Travel-Guide-Accommodation)
-   [Guest Houses in Sheffield](https://expedia.ca/Sheffield-Guest-Houses.d157238-aaGuestHouses.Travel-Guide-Accommodation)
-   [Inns in Sheffield](https://expedia.ca/Sheffield-Inns.d157238-aaInns.Travel-Guide-Accommodation)
-   [Resorts in Sheffield](https://expedia.ca/Sheffield-Resort-Hotels.d157238-aaResortHotels.Travel-Guide-Accommodation)
-   [Lodges in Sheffield](https://expedia.ca/Sheffield-Lodges.d157238-aaLodges.Travel-Guide-Accommodation)
-   [Aparthotels in Sheffield](https://expedia.ca/Sheffield-Apart-Hotels.d157238-aaApartHotels.Travel-Guide-Accommodation)
-   [Chalets in Sheffield](https://expedia.ca/Sheffield-Chalets.d157238-aaChalets.Travel-Guide-Accommodation)
-   [Villas in Sheffield](https://expedia.ca/Sheffield-Villas.d157238-aaVillas.Travel-Guide-Accommodation)
-   [Condo Resorts in Sheffield](https://expedia.ca/Sheffield-Condominium-Resort.d157238-aaCondominiumResort.Travel-Guide-Accommodation)
-   [Country Houses in Sheffield](https://expedia.ca/Sheffield-Country-House.d157238-aaCountryHouse.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Sheffield?

> Yes, you can find vacation rentals near popular attractions in Sheffield, or you can select a more secluded option if you'd like a relaxing place to stay. Sheffield is known for its casinos and local tours.

### What are some of the best vacation rentals that Sheffield has to offer?

> [Antique Farmhouse Totally Restored](https://www.expedia.ca/Sheffield-Hotels-Antique-Farmhouse-Totally-Restored.h27129515.Hotel-Information) : This highly rated vacation home rental in Sheffield is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

### How many vacation rentals are there in Sheffield?

> With 24 Expedia vacation rentals, you're sure to find just the right place for your Sheffield stay.

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

> Housatonic River and Thom Reed UFO Monument Park are a couple of scenic spots to enjoy the outdoors, whereas Ashley House is one of the cultural attractions. While here, Magnolia Bluffs Casino and Mount Everett State Reservation are other places worth a visit.

### What are vacation rentals like in Sheffield?

> Vacation rentals are private accommodations you can stay in for a couple days or more in Sheffield. Vacation rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip.

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)