Title: Bennington Vacation Home Rentals from CA $342: Search Top Private Vacation Homes for Rent | Expedia.ca

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![Historic Henry Covered bridge over the Walloomsac River e in Bennington, Vermont](https://images.trvl-media.com/place/6057349/ddd79da6-d04a-4703-8452-12989539524e.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6057349/ddd79da6-d04a-4703-8452-12989539524e.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

Next weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Bennington vacation homes

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89710000/89700500/89700465/w906h683x59y0-81ea00c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89710000/89700500/89700465/w905h683x60y0-69b1532d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89710000/89700500/89700465/w506h639x259y44-0fd7b2c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/90000000/89710000/89700500/89700465/w904h683x60y0-62d4a56d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Shaftsbury

[](https://www.expedia.ca/Shaftsbury-Hotels-Peaceful-Country-Getaway-Birds-Of-A-Feather-Farm.h89700465.Hotel-Information)

9.8/10

Exceptional

(30 reviews)

"Great place!!"

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

Margaret D.

CA $137

CA $342 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Shaftsbury-Hotels-Peaceful-Country-Getaway-Birds-Of-A-Feather-Farm.h89700465.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/493cc38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/aac07fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/775a6169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/e8d7246a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bennington

[](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h61478133.Hotel-Information)

8.6/10

Excellent

(34 reviews)

"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."

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

Malika R.

CA $139

CA $377 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h61478133.Hotel-Information)

![House, 4 Bedrooms | View from property](https://images.trvl-media.com/lodging/108000000/107450000/107440200/107440119/0ea6dc03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 4 Bedrooms | Living area](https://images.trvl-media.com/lodging/108000000/107450000/107440200/107440119/bd3444bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 4 Bedrooms | Exterior](https://images.trvl-media.com/lodging/108000000/107450000/107440200/107440119/e18f03fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 4 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/108000000/107450000/107440200/107440119/bb9d574f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Arlington

[](https://www.expedia.ca/Arlington-Hotels-Bear-Pass-Mountain-View-4-Bedroom-Home.h107440119.Hotel-Information)

8.0/10

Very good

(1 review)

"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "

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

Manish

CA $351

CA $953 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Arlington-Hotels-Bear-Pass-Mountain-View-4-Bedroom-Home.h107440119.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/100000000/100000000/99995200/99995104/f89f88e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/100000000/99995200/99995104/96f31790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/100000000/99995200/99995104/c1c7a003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/100000000/99995200/99995104/6a0a6f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Dorset

[](https://www.expedia.ca/Dorset-Hotels-Charming-Dorset-Cottage-Retreat.h99995104.Hotel-Information)

10/10

Exceptional

(7 reviews)

"We had a wonderful stay at this beautiful, cozy cottage in Dorset. It’s close to multiple ski mountains and the charming town of Manchester, and the hosts were super friendly and helpful. Check-in and check-out were easy, and the place was just as advertised."

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

Sarah S.

CA $412

CA $1,017 total

includes taxes & fees

Jan 23 - Jan 24

[](https://www.expedia.ca/Dorset-Hotels-Charming-Dorset-Cottage-Retreat.h99995104.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/620d544b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/cea2d009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/a4954c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, internet, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/5f732777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stratton

[](https://www.expedia.ca/Stratton-Hotels-Stratton-Mountain-Condo-With-Shared-Pool.h44577227.Hotel-Information)

7.8/10

Good

(53 reviews)

"Location was great, pool, hot tubs and sauna were great"

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

Lin M.

CA $208

CA $555 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Stratton-Hotels-Stratton-Mountain-Condo-With-Shared-Pool.h44577227.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/f70a0c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/ef3ff692.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/a4c7760d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/3b2bff89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Manchester Center

[](https://www.expedia.ca/Manchester-Center-Hotels-6-Bed-7-Bath-VT-Retreat-Rent-A-Former-BB-Greybourne-House.h62953803.Hotel-Information)

10/10

Exceptional

(51 reviews)

"Had a great time."

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

Neetesh B.

CA $1,340

CA $2,846 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Manchester-Center-Hotels-6-Bed-7-Bath-VT-Retreat-Rent-A-Former-BB-Greybourne-House.h62953803.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/108000000/107450000/107442100/107442045/72524433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/108000000/107450000/107442100/107442045/7ad5d53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107450000/107442100/107442045/da47d03a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/108000000/107450000/107442100/107442045/bb7a012d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sunderland

[](https://www.expedia.ca/Arlington-Hotels-NEW-LISTING-Bear-Pass-Mountain-View.h107442045.Hotel-Information)

9.6/10

Exceptional

(5 reviews)

"We loved our stay at Bear Pass! The kitchen was more than adequately stocked. The hous was great for our extended family and our 3 dogs"

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

Megan G.

CA $349

CA $953 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Arlington-Hotels-NEW-LISTING-Bear-Pass-Mountain-View.h107442045.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/59f7968b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/f45bf329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/27adae20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/1562dce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Jamaica

[](https://www.expedia.ca/Bondville-Hotels-The-Mountain-Escape.h96211209.Hotel-Information)

9.6/10

Exceptional

(23 reviews)

"Absolutely a wonderful place to vacation. The house is comfortable and warming. The hosts went above and beyond to make our stay great and responded to our questions promptly. We will definitely rent again. "

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

Lee Anna C.

CA $514

CA $1,425 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Bondville-Hotels-The-Mountain-Escape.h96211209.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/125000000/124840000/124831400/124831341/w1468h1698x5y7-0fca0d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/125000000/124840000/124831400/124831341/9f02519d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124840000/124831400/124831341/48c4f4f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124840000/124831400/124831341/3a451809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winhall

[](https://www.expedia.ca/Bondville-Hotels-Vacation-On-Stratton-Mountain-On-The-High-Meadow-Ski-Shuttle-Route.h124831341.Hotel-Information)

CA $1,666

CA $2,642 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Bondville-Hotels-Vacation-On-Stratton-Mountain-On-The-High-Meadow-Ski-Shuttle-Route.h124831341.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/61fb65d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/60ac265f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/395f0ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/2e63fc6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Jamaica

[](https://www.expedia.ca/Bondville-Hotels-Mountain-Oasis-Hot-Tub.h76905876.Hotel-Information)

9.8/10

Exceptional

(27 reviews)

"EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)."

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

s w.

CA $434

CA $1,323 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Bondville-Hotels-Mountain-Oasis-Hot-Tub.h76905876.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/c7eb5681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic House](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/8c452d97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic House | Private kitchen](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/f721b80c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic House | Water view](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/7c1d02ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bennington

[](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h83780792.Hotel-Information)

4.8/10

(3 reviews)

"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...

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

Hunter

[](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h83780792.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120120000/120119000/120119000/b59ee24f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/121000000/120120000/120119000/120119000/09390848.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120120000/120119000/120119000/23b2b069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120120000/120119000/120119000/bf994535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Manchester

[](https://www.expedia.ca/Manchester-Center-Hotels-Cozy-3-Bedroom.h120119000.Hotel-Information)

CA $317

CA $787 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Manchester-Center-Hotels-Cozy-3-Bedroom.h120119000.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113720000/113710300/113710276/w1393h936x1y12-5bebcec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113720000/113710300/113710276/w1420h947x0y5-a2305446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113720000/113710300/113710276/w1423h949x1y5-23f99f41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113720000/113710300/113710276/w1394h930x1y12-1cf69565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stratton

[](https://www.expedia.ca/Stratton-Hotels-Luxury-Slopeside-Ski-Inski-Out-Getaway-With-Hot-Tub.h113710276.Hotel-Information)

10/10

Exceptional

(1 review)

"Katherine was a perfect host. The house is beautiful and had everything we needed for our family vacation. Thank you so much! "

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

Katryn B.

CA $1,667

CA $2,410 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Stratton-Hotels-Luxury-Slopeside-Ski-Inski-Out-Getaway-With-Hot-Tub.h113710276.Hotel-Information)

![TV, fireplace, books, music library](https://images.trvl-media.com/lodging/112000000/111940000/111931800/111931794/37921a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111940000/111931800/111931794/fab14dd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111940000/111931800/111931794/ae326dac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111940000/111931800/111931794/ed0261b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winhall

[](https://www.expedia.ca/Bondville-Hotels-Spacious-Mountain-Retreat.h111931794.Hotel-Information)

10/10

Exceptional

(9 reviews)

"Great location, large space for family, good amenities, love the fireplace and coffee set up."

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

Eitan S.

CA $719

CA $1,511 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Bondville-Hotels-Spacious-Mountain-Retreat.h111931794.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109090000/109080100/109080071/c88b308c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/110000000/109090000/109080100/109080071/ef1f0e3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/110000000/109090000/109080100/109080071/5ae4ca5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109090000/109080100/109080071/eef373e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winhall

[](https://www.expedia.ca/Bondville-Hotels-Gorgeous-Views.h109080071.Hotel-Information)

9.6/10

Exceptional

(15 reviews)

"Beautiful, very comfortable and cozy house. We enjoyed staying here. Probably will come more."

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

olena d.

CA $833

CA $1,582 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Bondville-Hotels-Gorgeous-Views.h109080071.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91760000/91754400/91754323/c7361572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/92000000/91760000/91754400/91754323/75682f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/92000000/91760000/91754400/91754323/5cb1eef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91760000/91754400/91754323/49345747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winhall

[](https://www.expedia.ca/Bondville-Hotels-Stratton-ChaletbrBeautiful-Pet-Friendly-Chalet-With-Hot-Tub.h91754323.Hotel-Information)

9.6/10

Exceptional

(33 reviews)

"Our family had a wonderful time staying in this home."

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

Meghan C.

CA $508

CA $1,187 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Bondville-Hotels-Stratton-ChaletbrBeautiful-Pet-Friendly-Chalet-With-Hot-Tub.h91754323.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/6c6cf45f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/5dc2bebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/12b81391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/972c3b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Florida

[](https://www.expedia.ca/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.Hotel-Information)

10/10

Exceptional

(4 reviews)

"Place was super clean. Beds were comfortable. Location was great."

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

Tristan e.

CA $255

CA $474 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/c4a5d927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/ba382757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/98acb809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/929abf3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hoosick Falls

[](https://www.expedia.ca/Hoosick-Falls-Hotels-Cozy-Ski-Retreat-With-New-Pet-Yard-And-Many-Upgrades-Close-To-3-Ski-Areas.h40226569.Hotel-Information)

9.8/10

Exceptional

(101 reviews)

"Beautiful, serene location with great penned in area for my lovable, niece pup! Spacious house with all the key amenities. Easy access for my elederly mom. "

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

Lynn F.

CA $161

CA $429 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Hoosick-Falls-Hotels-Cozy-Ski-Retreat-With-New-Pet-Yard-And-Many-Upgrades-Close-To-3-Ski-Areas.h40226569.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/2f78aa12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/20e7ddaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/09a3de30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/04847bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Charlemont

[](https://www.expedia.ca/Charlemont-Hotels-Charlemont-Chalet-Where-The-Mountains-Meet-Luxury.h121902882.Hotel-Information)

CA $510

CA $939 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Charlemont-Hotels-Charlemont-Chalet-Where-The-Mountains-Meet-Luxury.h121902882.Hotel-Information)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/3e9df2f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/0444e51c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/098ed9b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/29b5b165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Londonderry

[](https://www.expedia.ca/Londonderry-Hotels-Enjoy-This-Authentic-And-Cozy-VT-Barn-With-Brand-New-Hot-Tub.h106674947.Hotel-Information)

8.0/10

Very good

(1 review)

"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "

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

Christine M.

CA $352

CA $693 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Londonderry-Hotels-Enjoy-This-Authentic-And-Cozy-VT-Barn-With-Brand-New-Hot-Tub.h106674947.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=2026-01-30&endDate=2026-01-31&regionId=6057349&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=APART_HOTEL)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CHALET)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America&regionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VILLA)

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## Top Bennington Hotel Reviews

![The Four Chimneys Inn](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/a1fa9bf1_y.jpg)

### The Four Chimneys Inn

10/10 Excellent

"This is a quintessential Vermont inn in beautiful historic Bennington. The inn was lovingly cared for by the owner who was very attentive to his guests. We will stay again."

[](https://expedia.ca/Bennington-Hotels-The-Four-Chimneys-Inn.h2394036.Hotel-Information)

![Harwood Hill Motel](https://images.trvl-media.com/lodging/13000000/12360000/12354600/12354542/ffee6d77_y.jpg)

### Harwood Hill Motel

10/10 Excellent

"Clean room & courteous staff. "

[](https://expedia.ca/Bennington-Hotels-Harwood-Hill-Motel.h12354542.Hotel-Information)

![Hotel Vervana, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/b33626c2_y.jpg)

### Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent

"Staff were great and very accommodating. Room is very nice and spacious. Great hotel"

[](https://expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information)

![Hampton Inn Bennington](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/aadd5504_y.jpg)

### Hampton Inn Bennington

10/10 Excellent

"Good Beautiful stay"

[](https://expedia.ca/Bennington-Hotels-Hampton-Inn-Bennington.h1191981.Hotel-Information)

![Knotty Pine](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/439bea3f_y.jpg)

### Knotty Pine

10/10 Excellent

"Check in was great"

[](https://expedia.ca/Bennington-Hotels-Knotty-Pine.h119106200.Hotel-Information)

![South Shire](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/0f420ffa_y.jpg)

### South Shire

10/10 Excellent

"A+ service, room we stayed in was perfect size with king bed. had an issue with heater first night but Inn Keeper was great to deal with and provided alternative heat source on first evening plus they have working fireplace (bonus++). We stayed 3 nights and just enjoyed ourselves during our visit. would definitely stay here again."

[](https://expedia.ca/Bennington-Hotels-South-Shire.h76163190.Hotel-Information)

![Best Western Bennington](https://images.trvl-media.com/lodging/1000000/20000/16400/16323/5ad1b90e_y.jpg)

### Best Western Bennington

10/10 Excellent

"Clean room and comfortable "

[](https://expedia.ca/Bennington-Hotels-Best-Western-Bennington.h16323.Hotel-Information)

![Charming 2-bedroom apartment in superb Bennington with WiFi](https://images.trvl-media.com/lodging/111000000/110940000/110935900/110935832/95f762a8_y.jpg)

### Charming 2-bedroom apartment in superb Bennington with WiFi

10/10 Excellent

"One of the coolest places ive stayed from vrbo"

[](https://expedia.ca/Bennington-Hotels-Charming-2-Bedroom-Apartment-In-Superb-Bennington-With-WiFi.h110935832.Hotel-Information)

![One of a kind VT Renovated Barn- Cozy All Season and Holiday Retreat](https://images.trvl-media.com/lodging/55000000/54130000/54124000/54123926/8992719c_y.jpg)

### One of a kind VT Renovated Barn- Cozy All Season and Holiday Retreat

10/10 Excellent

"Incredible converted barn made such an atmospheric place to stay after hiking the green mountains with our dog. All was clean and worked really well. We really enjoyed sitting by the huge fireplace every evening - we’d return immediately if we could!"

[](https://expedia.ca/Bennington-Hotels-Cozy-One-Of-A-Kind-Renovated-Barn-Ultimate-Getaway.h54123926.Hotel-Information)

## Find out more about Bennington

## Bennington Vacation Homes information

| Number of reviews | 367                |
| ----------------- | ------------------ |
| Accommodation     | 238 Vacation Homes |
| Lowest Price      | CA $342            |
| Highest Price     | CA $3,677          |

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- [Book Vacation Homes in Bennington on Expedia.com ](https://www.expedia.com/Bennington-Private-Vacation-Homes.d6057349-aaPrivateVacationHomes.Travel-Guide-Accommodation)