Title: Windsor Vacation Home Rentals from CA $233: Search Top Private Vacation Homes for Rent | Expedia.ca

  

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# Windsor Vacation Rentals

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## Check prices for these dates

Next weekend

[Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Windsor Vacation Homes

![Interior](https://images.trvl-media.com/lodging/64000000/63950000/63942500/63942414/815e1d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/64000000/63950000/63942500/63942414/5ad0db17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/64000000/63950000/63942500/63942414/450d67d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/64000000/63950000/63942500/63942414/af77614e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful home offering privacy on 7 acres with private pond

West Windsor

10/10

Exceptional

(30)

"Very relaxing house, we all enjoyed the fireplaces and pellet stove and the well-equipped kitchen allowed us to cook beautiful meals. The property is gorgeous and neighbors are far away. This was the perfect place for a friends reunion/ski trip!"

CA $308

CA $715 total

includes taxes & fees

Oct 19 - Oct 20

[](https://www.expedia.ca/Windsor-Hotels-Beautiful-Home-Offering-Privacy-On-7-Acres-With-Private-Pond.h63942414.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/ea91e459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/906f227a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097860/2fbac199.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/120000000/119100000/119097900/119097860/d8ed7a65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Condo Tucked in the Heart of Killington

Killington

CA $141

CA $424 total

includes taxes & fees

Oct 7 - Oct 8

[](https://www.expedia.ca/Killington-Hotels-Luxury-Condo-Tucked-In-The-Heart-Of-Killington.h119097860.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/c9400bbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/acc10e06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/adb899cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100510000/100501900/100501897/f1b12770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### CozyDen - AC, Grill, Bike to Mountain, Porch!

Killington

10/10

Exceptional

(1)

"Very quiet and private feeling even though it is in a condo like setting. Very clean, and had all the conveniences we needed (A/C, coffee maker, full kitchen appliances). And so kind and personal to leave some souvenirs of the area. We felt very comfortable when every we finished our day of sightseeing to come back to our home away from home. "

CA $131

CA $404 total

includes taxes & fees

Oct 23 - Oct 24

[](https://www.expedia.ca/Killington-Hotels-CozyDen-AC.h100501897.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/dcbc9b92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/42b859a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/47ba2040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105780000/105777700/105777639/53d0c8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

Killington

10/10

Exceptional

(1)

"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "

CA $238

CA $765 total

includes taxes & fees

Oct 7 - Oct 8

[](https://www.expedia.ca/Killington-Hotels-Fun-In-Fun-Out-Ski-Home-Main-Floor-Renovated-3BR2BA-Hot-Tub-Lift-Tickets.h105777639.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/9e5ceac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/6b0e5b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/83d1a856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/367a6860.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lake Front Family Friendly Escape

Newport

10/10

Exceptional

(4)

"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"

CA $206

CA $552 total

includes taxes & fees

Oct 15 - Oct 16

[](https://www.expedia.ca/Newport-Hotels-Lake-Front-Family-Friendly-Escape.h100538389.Hotel-Information)

![Golf](https://images.trvl-media.com/lodging/102000000/101250000/101243900/101243826/c575999d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101250000/101243900/101243826/404aed07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101250000/101243900/101243826/deca5e87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/102000000/101250000/101243900/101243826/45e652e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Grizz- AC, Pool, Sauna, Gym, Near Resort

Killington

10/10

Exceptional

(4)

"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "

CA $154

CA $614 total

includes taxes & fees

Oct 7 - Oct 8

[](https://www.expedia.ca/Killington-Hotels-TheGrizz-Bike-And-Ski-Shuttle-On-Off-By-Golf.h101243826.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60670000/60662500/60662471/aff31f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/61000000/60670000/60662500/60662471/9636317e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/61000000/60670000/60662500/60662471/9e08470f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/61000000/60670000/60662500/60662471/67f97b9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic Farmhouse Decor | Deck w/View

Sunapee

10/10

Exceptional

(51)

"Great cabin about 2 minutes from Mt. Sunapee resort and state park, as well as several lake towns. Beds are extra comfortable and the kitchen has everything we needed. "

CA $280

CA $599 total

includes taxes & fees

Oct 6 - Oct 7

[](https://www.expedia.ca/Sunapee-Hotels-Chic-Farmhouse-Decor-Deck-Wview.h60662471.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/108000000/107610000/107603000/107602909/91d96e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107610000/107603000/107602909/9aa73663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/108000000/107610000/107603000/107602909/7a3d64b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/108000000/107610000/107603000/107602909/fbaf812d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### @SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

Sunapee

10/10

Exceptional

(16)

"We greatly enjoyed a quick get away to this beautiful sun-filled house! The house was exceptionally clean and comfortable, very relaxing place to stay! "

CA $251

CA $648 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Sunapee-Hotels-SunapeeSeasonsAcross-From-Dewey-Beach.h107602909.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/8d25e78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/96ddc65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/ac990b4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/85ba9de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Carol - 10 minutes to Okemo & Newly Renovated

Cavendish

10/10

Exceptional

(6)

"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"

CA $220

CA $415 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Cavendish-Hotels-The-Carol-Styled-And-Freshly-Renovated-Stay10-Minutes-To-Okemo.h101895664.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/4a76f043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/3018839a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/1083183d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/121000000/120660000/120652400/120652390/28fc792a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Killington

CA $200

CA $532 total

includes taxes & fees

Oct 6 - Oct 7

[](https://www.expedia.ca/Killington-Hotels-Cozy-2BR-Mountain-Retreat-Near-Killington-Resort-Pet-Friendly-W-Fireplace.h120652390.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104790000/104789700/104789606/1c960e95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104790000/104789700/104789606/c038023d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104790000/104789700/104789606/be338c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/105000000/104790000/104789700/104789606/b4350eb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Powder Park Place: Lower Unit. Cozy and close to the Mountain! Discounted ski rentals.

Killington

10/10

Exceptional

(2)

"A very comfortable stay for a family of four. Close to everything, clean, well stocked for breakfast making, and just enough room for everyone. We really enjoyed the fireplace after a day of skiing.Not sure why the heat setting turned to low 60s every night, but our blankets were warm."

CA $178

CA $593 total

includes taxes & fees

Oct 6 - Oct 7

[](https://www.expedia.ca/Killington-Hotels-Powder-Park-Place-Lower-Unit-Cozy-And-Close-To-The-Mountain-Discounted-Lift-Tickets.h104789606.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/56000000/55190000/55184800/55184767/eec7f68a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/56000000/55190000/55184800/55184767/aa49b005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, streaming services, music library, video library](https://images.trvl-media.com/lodging/56000000/55190000/55184800/55184767/8ea18e84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, streaming services, music library, video library](https://images.trvl-media.com/lodging/56000000/55190000/55184800/55184767/fd2ba366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Breakaway House: Renovated Killington Duplex, Unit A. Close to Resort.

Killington

7.6/10

Good

(4)

"Great location, clean and quiet."

CA $204

CA $644 total

includes taxes & fees

Oct 6 - Oct 7

[](https://www.expedia.ca/Killington-Hotels-Breakaway-House-Renovated-Killington-Duplex.h55184767.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114880000/114878200/114878131/w1920h1286x0y3-bf724441.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/115000000/114880000/114878200/114878131/w1920h1286x0y3-6166af9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114880000/114878200/114878131/w1920h1286x0y3-6a24e5ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video library, stereo](https://images.trvl-media.com/lodging/115000000/114880000/114878200/114878131/3db9aac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 2BR/3BA Killington Condo w/ EV Charger, Ski Discounts & Pool

The Woods

10/10

Exceptional

(1)

"Great location! Check in and check out process was super easy. Loved it!"

CA $206

CA $613 total

includes taxes & fees

Oct 7 - Oct 8

[](https://www.expedia.ca/Killington-Hotels-Spacious-2BR3BA-Killington-Condo-W-EV-Charger.h114878131.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/0a51ad2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/17915502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/4a020446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/f922de49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Bridgewater

9.4/10

Exceptional

(16)

"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "

CA $191

CA $686 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Bridgewater-Corners-Hotels-NEW-Blueberry-Hill-Escape-Pet-Friendly-King-Bed-Fire-Pit-Grill.h78342432.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/47000000/46560000/46559000/46558949/4a6f7251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/47000000/46560000/46559000/46558949/a51a1789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/47000000/46560000/46559000/46558949/50d52884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/47000000/46560000/46559000/46558949/2672846a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Brook Road Condo

Goshen

8.8/10

Excellent

(14)

"Nice place close to the mountain!"

CA $225

CA $436 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Goshen-Hotels-Brook-Road-Condo.h46558949.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/112000000/111420000/111411200/111411190/5e2fb8ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111420000/111411200/111411190/0326abbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111420000/111411200/111411190/5200e83b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111420000/111411200/111411190/d6f36570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Pomfret

10/10

Exceptional

(1)

"Beautiful, spacious, clean, relaxing home and property. Loved it! Would stay here again."

CA $426

CA $806 total

includes taxes & fees

Oct 22 - Oct 23

[](https://www.expedia.ca/South-Pomfret-Hotels-Peaceful-Oasis.h111411190.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/103000000/102050000/102041800/102041769/5e4f8629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/103000000/102050000/102041800/102041769/e0adb8d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102050000/102041800/102041769/99f67bb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102050000/102041800/102041769/a8742ff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hot Tub | Firepit | Dog-Friendly | Golf | Foliage

Killington

8.0/10

Very good

(1)

"Place was nice a cozy. Had a minor issue that was communicated quickly and resolved."

CA $345

CA $993 total

includes taxes & fees

Oct 15 - Oct 16

[](https://www.expedia.ca/Killington-Hotels-Hot-Tub-Sauna-The-Tower-House.h102041769.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116020000/116017200/116017103/e0bce399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116020000/116017200/116017103/f43678e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116020000/116017200/116017103/71cad224.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/117000000/116020000/116017200/116017103/c75315f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Main Street Retreat 4-bedroom w Hot Tub, Walk to Beach, Harbor & Restaurants

Sunapee

10/10

Exceptional

(2)

"Great location. Fun weekend. House nicely maintained and supplied. "

CA $488

CA $1,114 total

includes taxes & fees

Oct 6 - Oct 7

[](https://www.expedia.ca/Sunapee-Hotels-Main-Street-Retreat-4-Bedroom-Vacation-House-W-Hot-Tub-Walk-To-Beach-Harbor.h116017103.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/4e6773ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/0d26f53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/1f2d7230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/dd9dbbe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Whimsical Room & Private Bathroom in Historic Inn

Chester Depot

8.8/10

Excellent

(9)

"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"

CA $138

CA $233 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Chester-Hotels-Whimsical-Room-Private-Bathroom-In-Historic-Inn.h87135975.Hotel-Information)

![Smart TV, video games, books](https://images.trvl-media.com/lodging/118000000/117410000/117401300/117401265/53577443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117410000/117401300/117401265/e6bcf0dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117410000/117401300/117401265/599dc856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117410000/117401300/117401265/5cc5dbc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

Sunapee

9.0/10

Wonderful

(4)

"Great location to walk into town."

CA $488

CA $943 total

includes taxes & fees

Oct 12 - Oct 13

[](https://www.expedia.ca/Sunapee-Hotels-Charming-3-Bedroom-House-Walk-To-Sunapee-Harbor-And-Short-Drive-To-Mt-Sunapee.h117401265.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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## Top Windsor Hotel Reviews

![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg)

### Jackson Gore Village

10/10 Excellent

"We checked in and it went great. The staff was very friendly and accommodating at the front desk. We went to the restaurant for dinner around seven and were unable to be seated being told. It would be 835, we were good with that and waited at the bar. We never received a call. We followed up a couple of times with the hostess and ultimately ordered takeout from the bar.… jimmy at the bar was very helpful in getting our order in and out to us before the kitchen closed, which was in less than 10 minutes . We got we got to the room and first appearance It looked great until we retired for the night and the are bedding still had stain from previous use. Ultimately there has been some great and some really not so great experience – we’ll see what tomorrow brings.. "

[](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information)

![Hotel Coolidge](//images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg)

### Hotel Coolidge

10/10 Excellent

"Staff was so charming upon arrival. He offered us water and coffee. It was almost as if he knew we had a long journey. The room, we slept like babies. The twin sized beds were most comfortable for sleep. Living it up the hotel Coolidge. Such a lovely place!"

[](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.Hotel-Information)

![Holiday Inn Express Hotel & Suites White River Junction by IHG](//images.trvl-media.com/lodging/2000000/1140000/1138300/1138208/634c6a80_y.jpg)

### Holiday Inn Express Hotel & Suites White River Junction by IHG

10/10 Excellent

"A/c worked great. Big room. Clean. The free breakfast was good and had a wide variety. I liked that there were pillow options as well. "

[](https://expedia.ca/White-River-Junction-Hotels-Holiday-Inn-Express-Hotel-Suites-White-River-Junction.h1138208.Hotel-Information)

![Mountain Sports Inn](//images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg)

### Mountain Sports Inn

10/10 Excellent

"Great "

[](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information)

![Best Western West Lebanon-Hanover Hotel](//images.trvl-media.com/lodging/2000000/1210000/1200500/1200405/ef1c5364_y.jpg)

### Best Western West Lebanon-Hanover Hotel

10/10 Excellent

"Very quiet. Clean room. Hot breakfast included. Free coffee all day."

[](https://expedia.ca/Lebanon-Hotels-Best-Western-West-Lebanon-Hanover-Hotel.h1200405.Hotel-Information)

![White River Inn and Suites](//images.trvl-media.com/lodging/1000000/30000/28000/27933/f779e2ff_y.jpg)

### White River Inn and Suites

10/10 Excellent

"Clean quiet room"

[](https://expedia.ca/White-River-Junction-Hotels-White-River-Inn-And-Suites.h27933.Hotel-Information)

![Hilton Garden Inn Hanover Lebanon](//images.trvl-media.com/lodging/22000000/21500000/21490500/21490448/0ffc6821_y.jpg)

### Hilton Garden Inn Hanover Lebanon

10/10 Excellent

"Jess was great getting me checked in. Always so welcoming "

[](https://expedia.ca/Lebanon-Hotels-Hilton-Garden-Inn-HanoverLebanon.h21490448.Hotel-Information)

![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](//images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg)

### Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"Wonderful accommodation "

[](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information)

![Killington Mountain Lodge, Tapestry Collection by Hilton](//images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg)

### Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent

"Best place in Killington!"

[](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information)

## Find out more about Windsor

## Windsor Vacation Homes information

| Number of reviews | 112 |
| --- | --- |
| Accommodation | 763 Vacation Homes |
| Lowest Price | CA $233 |
| Highest Price | CA $1,114 |

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-   [Mt Ascutney State Park](https://www.expedia.ca/Mt-Ascutney-State-Park-Vermont.d6175264.Vacation-Attraction)
-   [Visit Perkinsville](https://www.expedia.ca/Perkinsville.dx184065)
-   [Quechee Gorge Bridge](https://www.expedia.ca/Quechee-Gorge-Bridge-White-River-Junction.d6139298.Vacation-Attraction)
-   [Visit South Woodstock](https://www.expedia.ca/South-Woodstock.dx6149659)
-   [The Sustainable Farmer](https://www.expedia.ca/The-Sustainable-Farmer-Windsor.d553248621532666964.Vacation-Attraction)

-   [Avis Rental Cars in Hartland](https://www.expedia.ca/Avis-Car-Rentals-In-Hartland.d6052375-c41.Car-Rental-Guide-Suppliers)

-   [Book Vacation Homes in Windsor on Expedia.com](https://www.expedia.com/Windsor-Private-Vacation-Homes.d7881-aaPrivateVacationHomes.Travel-Guide-Accommodation)