Title: Sheffield Vacation Rentals from CA $219: Short-Term Rentals for 2025 | Expedia.ca

 

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# Sheffield Vacation Rentals

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## Check prices for these dates

Tonight

[Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-11-04&endDate=2025-11-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-11-05&endDate=2025-11-06&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

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

Next weekend

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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)

![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)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/565807cf.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 $548

CA $969 total

includes taxes & fees

Nov 11 - Nov 12

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

![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/99d3f85f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/af920cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cheerful 3-bedroom cottage with woodstove

Sheffield

10/10

Exceptional

(40)

"The property was centrally located for skiing, and was a comfortable stay."

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

Kelly R.

CA $277

CA $634 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/220997f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/837f847a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/dd672984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/1ebb7045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sugar Shack - 300 square feet of pure sweetness.

Chatham

10/10

Exceptional

(3)

"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "

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

Sue G.

CA $302

CA $507 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Chatham-Hotels-Sugar-Shack-300-Square-Feet-Of-Pure-Sweetness.h107109194.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/84000000/83780000/83773100/83773039/72279dd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83780000/83773100/83773039/17688c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83780000/83773100/83773039/f53734be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83780000/83773100/83773039/1894b59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### HunnyHAUS: Deluxe TINY\*private spa\*walk to town

Chatham

10/10

Exceptional

(9)

"We had the best time here. The house is even cuter and cozier in person (which says a lot because the pictures are great!). The hot tub was a great luxury and the house is literally a 3 minute walk to town. So convenient! We also had a fire in the Viking tent one night which was fun. Heidi was super helpful and quick to respond to any queries during our stay. She even left rose petals on the bed and a bottle of Prosecco chilling in the fridge for us upon our arrival. I would stay here again in a...

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

Megan H.

CA $316

CA $580 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chatham-Hotels-HunnyHAUS-Deluxe-TINYprivate-Spawalk-To-Town.h83773039.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/143defff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/f7d742eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/10a12328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/c465f1b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### BLUSH: Boutique TINY home\*private spa\*walk to town

Chatham

10/10

Exceptional

(6)

"Perfect blend of decore, comfort, and function. We went to Tanglewood which was only a half hour away. Came back to hot tub and fire pit. Beds here are soooo comfy! This is our 2nd time here and won’t be our last."

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

Melissa D.

CA $282

CA $482 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Chatham-Hotels-BLUSH-Boutique-TINY-Home-W-Private-Spa-Walk-To-New-Yorks-Cutest-Village.h102806391.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)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f5477a61.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 $196

CA $219 total

includes taxes & fees

Dec 5 - Dec 6

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

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/3db87cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/e729bc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/1c3ab355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/31d52781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### CT Gate House Goshen CT, Gate House Goshen CT

Goshen

9.8/10

Exceptional

(7)

"Wonderful stay. It really is a gate house. The property is beautiful and the house is spacious. If I was eloquent,I could go on and on... "

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

Wilford

CA $166

CA $916 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.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)

![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/e0f691bb.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/85000000/84680000/84672900/84672833/c50e9e6c.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)

### Home in Great Barrington

Great Barrington

9.8/10

Exceptional

(25)

"We had a lovely one week stay at this property. The location was very convenient to all the restaurants and shops. The fall foliage was spectacular and truly enjoyed biking and hiking in the Berkshires."

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

Farida K.

CA $253

CA $413 total

includes taxes & fees

Nov 17 - Nov 18

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

![Property grounds](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/2278baae.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)

![Dining](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/80124d14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest

9.6/10

Exceptional

(8)

"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."

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

James D.

CA $225

CA $551 total

includes taxes & fees

Nov 6 - Nov 7

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

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/83d3f833_edited_d758.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)

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

### Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest

10/10

Exceptional

(3)

"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 $205

CA $530 total

includes taxes & fees

Nov 12 - Nov 13

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

![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)

![Exterior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/c57b8d60.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 $285

CA $415 total

includes taxes & fees

Nov 6 - Nov 7

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/505c31c2.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)

![Property grounds](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/53261c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/1bcf2f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Great Barrington Get Away

Great Barrington

9.4/10

Exceptional

(25)

"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"

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

Elizabeth G.

CA $401

CA $732 total

includes taxes & fees

Nov 6 - Nov 7

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

![TV, offices](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413825/4bb2b020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413825/5e3915f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413825/30b55645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413825/19d02397.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Brooks Motel: Exceptional Suite

Hillsdale

9.2/10

Wonderful

(5)

"The motel was well equipped, clean, and comfortable. It was especially suited for my travel with my dog."

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

Susan S.

CA $223

CA $282 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Hillsdale-Hotels-The-Brooks-Motel-Exceptional-Suite.h104413825.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/329257ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/a7b21f81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/a0287de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/04c3bec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bungalow in the Berkshires

Lee

10/10

Exceptional

(4)

"We had a lovely stay. Easy check in and communication was great. "

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

Dale G.

CA $387

CA $542 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Lee-Hotels-Bungalow-In-The-Berkshires.h111821595.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)

![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)

### 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 $599

CA $1,115 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)

![Interior](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/21b3ce2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/8f88ebfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/6f907e45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/eb2f9471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### rural, serene + sophisticated space

Red Hook

10/10

Exceptional

(7)

"A beautifully curated barn overlooking a picturesque landscape. Gregg, the owner, really cares and wants to make sure you have everything you need. We stayed over a weekend when we were attending a wedding in the area. It was so nice to have a place to relax amidst all the festivities. The birdsong and bullfrog chorus led us to some of the soundest sleep we’ve enjoyed in a long time. "

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

Kathryn

CA $275

CA $442 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Red-Hook-Hotels-Rural.h36245067.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/cef7f580.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/cc6d7fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/48ee7521.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/fc31b289.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The George is an elegant restored home in the Hudson Valley

Stanfordville

9.2/10

Wonderful

(5)

"Our group had a lovely experience at this idyllic horse farm in the Hudson Valley. The rental was very well appointed and spacious on beautiful grounds. Communication with the property owner was friendly, welcoming and prompt which is always appreciated when arranging a joint family vacation! Would highly recommend as a picturesque escape from the City to any country loving folks!"

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

Christina S.

CA $810

CA $1,288 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Stanfordville-Hotels-The-George-Is-An-Elegant-Restored-Home-In-The-Hudson-Valley.h104751955.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/772f14ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/61aeb8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/69c2e8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/2cdfc6fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

10/10

Exceptional

(1)

"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"

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

Roberta

CA $796

CA $1,867 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/9eeeead4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/0cd1f311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/6873f6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/4f2c31bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

CA $478

CA $826 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/ffa8b349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/f9a0c9d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/b650005a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/db74a893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale

8.4/10

Very good

(5)

"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "

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

Stefanie K.

CA $370

CA $870 total

includes taxes & fees

Dec 6 - Dec 7

[](https://www.expedia.ca/Hillsdale-Hotels-Perfect-House-In-Hillsdale.h100053078.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=2025-11-19&endDate=2025-11-20&regionId=157238&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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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

![Courtyard by Marriott Lenox Berkshires](//images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/b4c52f47_y.jpg)

### Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Yes, shops nearby. "

[](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.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

"I had a smooth check in. A little later I went back to the front desk to get an extra key, was asked my room number and last name. The associate, knew that I had asked for extra pillows when I made the reservation. I don't think he was even on my reservation on the computer yet to see the note. Asked if I had the extra pillows in the room and were they ok! Often hotels don't even notice this request, never mind remember it or ask about it. Great attention to details!"

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

![Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires](//images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551_y.jpg)

### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"The staff was welcoming and friendly and our room was excellent"

[](https://expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information)

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

### Berkshire Mountain Lodge

10/10 Excellent

"Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you"

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

"Clean and friendly "

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

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

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Staff was friendly, nice area, near things but set back so you didn’t hear the traffic."

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

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

### Monument Mountain Motel

10/10 Excellent

"Yes"

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

![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)

![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

"The room was spotless. The staff at arrival were very helpful. They sent texts that were helpful and reassuring. "

[](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.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 $219 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

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-   [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)
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-   [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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)