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

[Rupert Travel Guide](https://expedia.ca/Rupert.dx3000459728)[Hotels in Rupert](https://expedia.ca/Rupert-Hotels.d3000459728.Travel-Guide-Hotels)[Vacation Rentals in Rupert](https://expedia.ca/Rupert-Vacation-Rentals.d3000459728.Travel-Guide-VacationRentals)[Rupert Car Rentals](https://expedia.ca/Car-Rentals-In-Rupert.d3000459728.Car-Rental-Guide)[Rupert Vacation Packages](https://expedia.ca/Rupert.d3000459728.Destination-Travel-Guides)

![Vermont Foliage](https://images.trvl-media.com/place/3000459728/0596c53e-acf8-4425-a7ad-1840b2dc5352.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/3000459728/0596c53e-acf8-4425-a7ad-1840b2dc5352.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=3000459728&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 two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=3000459728&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)

In three months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=3000459728&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=3000459728&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Rupert 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)

![Interior](https://images.trvl-media.com/lodging/90000000/89710000/89700500/89700465/w505h683x260y0-3895f5aa.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)

![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)

![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)

![Exterior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/29b5b165.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)

![Interior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/0444e51c.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)

![Exterior](https://images.trvl-media.com/lodging/43000000/42540000/42537200/42537185/55ac514e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/43000000/42540000/42537200/42537185/6608b975.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/43000000/42540000/42537200/42537185/2a8a3947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/43000000/42540000/42537200/42537185/d31bb458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in shushan

[](https://www.expedia.ca/Cambridge-Hotels-Cozy-Rustic-Cabin-In-The-Hamlet-Of-Shushan-NY.h42537185.Hotel-Information)

9.6/10

Exceptional

(20 reviews)

"Lovely location, well appointed, dog friendly."

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

Anonymous traveller

CA $312

CA $523 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Cambridge-Hotels-Cozy-Rustic-Cabin-In-The-Hamlet-Of-Shushan-NY.h42537185.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/d295676b.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)

### 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)

![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 | Private kitchen](https://images.trvl-media.com/lodging/108000000/107450000/107440200/107440119/bb9d574f.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)

### 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](https://images.trvl-media.com/lodging/125000000/124540000/124538100/124538047/w1198h799x2y0-00d2a21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124540000/124538100/124538047/w2996h1998x4y0-035fc1b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/125000000/124540000/124538100/124538047/2a7ccda9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/125000000/124540000/124538100/124538047/68e0da24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Wardsboro

[](https://www.expedia.ca/West-Wardsboro-Hotels-Stratton-Woods-Secluded-Vermont-Cabin-Retreat.h124538047.Hotel-Information)

CA $237

CA $343 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/West-Wardsboro-Hotels-Stratton-Woods-Secluded-Vermont-Cabin-Retreat.h124538047.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)

![Exterior](https://images.trvl-media.com/lodging/100000000/100000000/99995200/99995104/5ada38fa.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/108000000/107450000/107442100/107442045/72524433.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)

![Exterior](https://images.trvl-media.com/lodging/108000000/107450000/107442100/107442045/da47d03a.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)

### 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 $904 total

includes taxes & fees

Jan 20 - Jan 21

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

![Interior](https://images.trvl-media.com/lodging/91000000/90950000/90944500/90944434/0304d4d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90950000/90944500/90944434/f9924319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90950000/90944500/90944434/538a1a5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90950000/90944500/90944434/763ae8ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Salem

[](https://www.expedia.ca/Salem-Hotels-ZenBarn-A-Quiet-Getaway.h90944434.Hotel-Information)

10/10

Exceptional

(2 reviews)

"This was a great spot to stay. The ski mountain was a hour away, but this was far more affordable and the drive to Okemo is lovely."

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

Casey O.

CA $417

CA $526 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Salem-Hotels-ZenBarn-A-Quiet-Getaway.h90944434.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)

![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)

![Interior](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/8abb59df.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)

![Exterior](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/59f7968b.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)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/e9ad80e9.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)

### 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 $515

CA $1,390 total

includes taxes & fees

Jan 19 - Jan 20

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/0e44f29d.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)

### 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 $478

CA $1,378 total

includes taxes & fees

Jan 21 - Jan 22

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

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106900000/106898600/106898502/78586c99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106900000/106898600/106898502/78d37ca8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/107000000/106900000/106898600/106898502/07748463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/107000000/106900000/106898600/106898502/74b11c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cambridge

[](https://www.expedia.ca/Cambridge-Hotels-Amanita-Dome-All-Inclusive-Food-And-Drinks.h106898502.Hotel-Information)

CA $415

CA $767 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Cambridge-Hotels-Amanita-Dome-All-Inclusive-Food-And-Drinks.h106898502.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/73000000/72290000/72281200/72281108/9a4f5d8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72290000/72281200/72281108/775424f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/73000000/72290000/72281200/72281108/26b2ee5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/73000000/72290000/72281200/72281108/a019d42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Jamaica

[](https://www.expedia.ca/Jamaica-Hotels-This-House-Is-A-4-Bedroom.h72281108.Hotel-Information)

9.0/10

Wonderful

(6 reviews)

"Great location. House was recently updated but has some older charm in parts. Fun and cozy. Hot tub was great the first day but smell seemed off the next day. Perhaps more chlorine was needed. Great time , great trip. Pet friendly is a bonus and the house looks never used so the cleaning crew is doing great work. Will rent again next year perhaps !"

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

Michael C.

CA $510

CA $1,075 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Jamaica-Hotels-This-House-Is-A-4-Bedroom.h72281108.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/96000000/95920000/95912600/95912570/ac01c9b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/96000000/95920000/95912600/95912570/5defd1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/96000000/95920000/95912600/95912570/1dd37ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95920000/95912600/95912570/8876e163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Wardsboro

[](https://www.expedia.ca/Wardsboro-Hotels-Stratton-Mt-Snow-Family-Getaway-With-Hot-Tub.h95912570.Hotel-Information)

10/10

Exceptional

(15 reviews)

"The house was beautiful and had everything we needed. We would definitely stay again"

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

Bonnie P.

CA $419

CA $1,065 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Wardsboro-Hotels-Stratton-Mt-Snow-Family-Getaway-With-Hot-Tub.h95912570.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)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120120000/120119000/120119000/ca1442d5.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)

![Exterior detail](https://images.trvl-media.com/lodging/121000000/120120000/120119000/120119000/09390848.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 $781 total

includes taxes & fees

Jan 20 - Jan 21

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91550000/91543200/91543112/81431cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91550000/91543200/91543112/fc11d51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91550000/91543200/91543112/13eea7cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91550000/91543200/91543112/6e6cdd0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stratton

[](https://www.expedia.ca/West-Wardsboro-Hotels-Cozy-Home-Mins-From-Stratton-Mount-Snow.h91543112.Hotel-Information)

10/10

Exceptional

(17 reviews)

"This house was amazing! The house was beautifully furnished and clean, and the workout equipment in the barn and the hot tub were great! We rented this with our extended family, and everyone agreed that this was one of the nicest houses that we have stayed in! We would definitely stay here again!"

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

Vicki W.

CA $667

CA $1,432 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/West-Wardsboro-Hotels-Cozy-Home-Mins-From-Stratton-Mount-Snow.h91543112.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)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91760000/91754400/91754323/7cb3cf11.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)

![Living area](https://images.trvl-media.com/lodging/114000000/113430000/113421000/113420944/abe6d0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113430000/113421000/113420944/35cee95a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113430000/113421000/113420944/db19ed42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113430000/113421000/113420944/77de0f67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Londonderry

[](https://www.expedia.ca/Londonderry-Hotels-Gorgeous-Couples-Barn-With-WiFi-Hot-Tub-In-Lovely-Londonderry.h113420944.Hotel-Information)

10/10

Exceptional

(2 reviews)

"The converted barn was absolutely stunning. Kitchen was well appointed and the family room spacious and comfortible."

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

Tim M.

CA $1,166

CA $1,774 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Londonderry-Hotels-Gorgeous-Couples-Barn-With-WiFi-Hot-Tub-In-Lovely-Londonderry.h113420944.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=2026-01-29&endDate=2026-01-30&regionId=3000459728&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Condos

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Private vacation homes

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America&regionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America&regionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CABIN)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America&regionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VILLA)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America&regionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CHALET)

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## Top Rupert Hotel Reviews

![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8_y.jpg)

### The Manchester View

10/10 Excellent

"Rooms were clean and they went above and beyond to check us in very early. I will definitely book again."

[](https://expedia.ca/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information)

![Sun Lodge](https://images.trvl-media.com/lodging/2000000/1160000/1157400/1157354/3e494820_y.jpg)

### Sun Lodge

10/10 Excellent

"Robin was very attentive. He has a very welcoming personality. I hope his hard work doesn’t go unnoticed! The hotel is beautiful. The bed was supper comfortable. "

[](https://expedia.ca/Bennington-Hotels-The-Lodge-At-Bromley.h1157354.Hotel-Information)

![Weathervane Motel](https://images.trvl-media.com/lodging/11000000/10430000/10429400/10429394/17ddc189_y.jpg)

### Weathervane Motel

10/10 Excellent

"Great everything"

[](https://expedia.ca/Bennington-Hotels-Weathervane-Motel.h10429394.Hotel-Information)

![Toll Road Inn](https://images.trvl-media.com/lodging/8000000/7660000/7652200/7652200/94368990_y.jpg)

### Toll Road Inn

10/10 Excellent

"Very cleen and friendly"

[](https://expedia.ca/Bennington-Hotels-Toll-Road-Inn.h7652200.Hotel-Information)

![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg)

### Hampton Inn and Suites Manchester

10/10 Excellent

"Super friendly staff! Pool and hot tub were also a hit. Room was very clean and spacious, bath was clean! I'd return! "

[](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information)

![The Olympia Lodge](https://images.trvl-media.com/lodging/10000000/9260000/9257700/9257616/c701f02d_y.jpg)

### The Olympia Lodge

10/10 Excellent

"Staff was nice"

[](https://expedia.ca/Bennington-Hotels-The-Olympia-Lodge.h9257616.Hotel-Information)

![The Inn at Manchester](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/534fcc92_y.jpg)

### The Inn at Manchester

10/10 Excellent

"super cute and clean, felt like home after not living there for 4 years!"

[](https://expedia.ca/Bennington-Hotels-The-Inn-At-Manchester.h1505817.Hotel-Information)

![Bromley View Inn](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/85d1c6cb_y.jpg)

### Bromley View Inn

10/10 Excellent

"Really cute simple clean ski lodge everything that you need and a great breakfast in the morning!"

[](https://expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information)

![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg)

### The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent

"Every thing was excellent "

[](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information)

## Find out more about Rupert

## Rupert Vacation Homes information

| Number of reviews | 258                |
| ----------------- | ------------------ |
| Accommodation     | 365 Vacation Homes |
| Lowest Price      | CA $342            |
| Highest Price     | CA $2,846          |

## Explore a world of travel with Expedia

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