Title: Winchendon Vacation Home Rentals from CA $390: Search Top Private Vacation Homes for Rent | Expedia.ca

[Hotels in Winchendon](https://expedia.ca/Winchendon-Hotels.d3000441689.Travel-Guide-Hotels)[Vacation Rentals in Winchendon](https://expedia.ca/Winchendon-Vacation-Rentals.d3000441689.Travel-Guide-VacationRentals)[Winchendon Car Rentals](https://expedia.ca/Car-Rentals-In-Winchendon.d3000441689.Car-Rental-Guide)[Winchendon Vacation Packages](https://expedia.ca/Winchendon.d3000441689.Destination-Travel-Guides)

![The Millers River in Winchendon, Massachusetts](https://images.trvl-media.com/place/3000441689/ee34b0fc-35dd-4fd4-bfe5-cd47ccc3b39d.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/3000441689/ee34b0fc-35dd-4fd4-bfe5-cd47ccc3b39d.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=3000441689&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=3000441689&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=3000441689&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=3000441689&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 Winchendon vacation homes

![WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124220000/124215600/124215586/a7ea3011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/125000000/124220000/124215600/124215586/7b34fd8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/125000000/124220000/124215600/124215586/ed45b7cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/125000000/124220000/124215600/124215586/f7a202b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Ashburnham

[](https://www.expedia.ca/Winchendon-Hotels-Spacious-Lakeside-4-Bedroom-House-In-Beautiful-Ashburnham.h124215586.Hotel-Information)

CA $278

CA $490 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Winchendon-Hotels-Spacious-Lakeside-4-Bedroom-House-In-Beautiful-Ashburnham.h124215586.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/bb59d3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/ee57533b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/0e213458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/af204105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winchendon

[](https://www.expedia.ca/Winchendon-Hotels-Enjoy-Your-Stay-In-An-Antique-Home-In-An-Antique-Toy-Museum.h83064044.Hotel-Information)

9.4/10

Exceptional

(8 reviews)

"What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!"

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

Katja Z.

CA $550

CA $728 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Winchendon-Hotels-Enjoy-Your-Stay-In-An-Antique-Home-In-An-Antique-Toy-Museum.h83064044.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/019323ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/ee17c612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/89c4c4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/b4c71f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Keene

[](https://www.expedia.ca/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.Hotel-Information)

9.6/10

Exceptional

(21 reviews)

"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."

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

Jack P.

CA $176

CA $390 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/125000000/124610000/124608400/124608310/4bf1abc7_edited_e750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124610000/124608400/124608310/w1162h877x25y27-a79385d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/125000000/124610000/124608400/124608310/05574cfb_edited_de51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124610000/124608400/124608310/0ce9bd25_edited_9861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Jaffrey

[](https://www.expedia.ca/Jaffrey-Hotels-Johns-Mountain-Hideaway.h124608310.Hotel-Information)

CA $282

CA $508 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Jaffrey-Hotels-Johns-Mountain-Hideaway.h124608310.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/8d9f525d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/e0a6d5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/4e846ae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/6cc8f8eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Keene

[](https://www.expedia.ca/Keene-Hotels-The-Leverett-House-In-Charming-Keene.h117913271.Hotel-Information)

10/10

Exceptional

(2 reviews)

"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...

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

Xilin J.

CA $294

CA $848 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Keene-Hotels-The-Leverett-House-In-Charming-Keene.h117913271.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/a9fb4c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/23ddfec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/65c29758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/fa175e1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Dublin

[](https://www.expedia.ca/Dublin-Hotels-5-Bedroom-Cozy-New-England-Home-Cobb-Meadow-House.h74153605.Hotel-Information)

10/10

Exceptional

(25 reviews)

"Good place to stay during a wedding week"

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

Veronique S.

CA $367

CA $738 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Dublin-Hotels-5-Bedroom-Cozy-New-England-Home-Cobb-Meadow-House.h74153605.Hotel-Information)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/123000000/122980000/122979900/122979859/807a35e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122980000/122979900/122979859/affd76f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Internet, bed sheets](https://images.trvl-media.com/lodging/123000000/122980000/122979900/122979859/80d199f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/123000000/122980000/122979900/122979859/0defd94d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Ashburnham

[](https://www.expedia.ca/Ashburnham-Hotels-NEW-Cushing-Home-Family-Cabin-Near-Wachusett-Mtn.h122979859.Hotel-Information)

[](https://www.expedia.ca/Ashburnham-Hotels-NEW-Cushing-Home-Family-Cabin-Near-Wachusett-Mtn.h122979859.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=2026-02-01&endDate=2026-02-02&regionId=3000441689&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=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=COTTAGE)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=VACATION_HOME)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CHALET)

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## Top Winchendon Hotel Reviews

![Chocksett Inn and Restaurant](https://images.trvl-media.com/lodging/2000000/1210000/1202200/1202140/2e99d26e_y.jpg)

### Chocksett Inn and Restaurant

10/10 Excellent

"The staff was very accommodating and friendly. Quaint place to stay. "

[](https://expedia.ca/Sterling-Hotels-Chocksett-Inn-And-Restaurant.h1202140.Hotel-Information)

![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg)

### The Colonial Hotel

10/10 Excellent

"Well-kept hotel with a great restaurant."

[](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information)

![Motel 6 Leominster, MA](https://images.trvl-media.com/lodging/1000000/1000000/996200/996152/fe9126d0_y.jpg)

### Motel 6 Leominster, MA

10/10 Excellent

"Clean room and friendly staff!"

[](https://expedia.ca/Leominster-Hotels-Motel-6-Leominster.h996152.Hotel-Information)

![Doubletree by Hilton Hotel Leominster](https://images.trvl-media.com/lodging/1000000/20000/16700/16645/7570cba8_y.jpg)

### Doubletree by Hilton Hotel Leominster

10/10 Excellent

"yes and yes"

[](https://expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.Hotel-Information)

![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg)

### Best Western Plus Keene Hotel

10/10 Excellent

"There was a college sports team staying there and were slamming doors until 1am. Send someone to walk the halls occasionally."

[](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information)

![Great Wolf Lodge Boston / Fitchburg, MA](https://images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/19aa1fc1_y.jpg)

### Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent

"Room was clean. Hotel was wonderful. Great activities. The staff was so friendly!! "

[](https://expedia.ca/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.Hotel-Information)

![Fairfield Inn & Suites by Marriott Keene Downtown](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/41372bd7_y.jpg)

### Fairfield Inn & Suites by Marriott Keene Downtown

10/10 Excellent

"Everything was clean, comfortable and the staff quite conversational"

[](https://expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.Hotel-Information)

![Hampton Inn & Suites Keene](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/189b6d07_y.jpg)

### Hampton Inn & Suites Keene

10/10 Excellent

"I reserved 2 rooms to accommodate my daughter and 4 grandchildren. We were met by a very welcoming staff who gave me adjoining rooms. The rooms provided enough individual spots for building Lego’s and playing with dinosaurs and even space for the youngest to safely run between the rooms. The heated pool was the highlight of our weekend; it was secure, well lit and a place where we all had the most family time fun."

[](https://expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information)

![Riverhouse by Weekender (Formerly Jack Daniels Inn)](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/5d62062a_y.jpg)

### Riverhouse by Weekender (Formerly Jack Daniels Inn)

10/10 Excellent

"Beds were sooo comfortable "

[](https://expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.Hotel-Information)

## Find out more about Winchendon

## Winchendon Vacation Homes information

| Number of reviews | 48                |
| ----------------- | ----------------- |
| Accommodation     | 45 Vacation Homes |
| Lowest Price      | CA $390           |
| Highest Price     | CA $848           |

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