Title: Winchendon Vacation Rentals from CA $360: Short-Term Rentals for 2026 | Expedia.ca

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![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

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two 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 three 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)

In four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2026-06-05&endDate=2026-06-07&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 rentals

![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)

![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)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124220000/124215600/124215586/9ef8fd65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious lakeside 4-bedroom house in beautiful Ashburnham

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

Ashburnham

CA $271

CA $489 total

includes taxes & fees

Feb 23 - Feb 24

[](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)

![Dining](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/870b92e3.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)

### Enjoy your stay in an antique home in an antique toy museum!

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

Winchendon

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 $535

CA $709 total

includes taxes & fees

Feb 17 - Feb 18

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

![Property grounds](https://images.trvl-media.com/lodging/115000000/114350000/114347300/114347249/w906h683x59y0-4987278f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/115000000/114350000/114347300/114347249/32163bc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/115000000/114350000/114347300/114347249/w906h683x59y0-8a316277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114350000/114347300/114347249/w507h683x259y0-5a689048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage beside a waterfall

[](https://www.expedia.ca/Wilton-Hotels-Cottage-Beside-A-Waterfall.h114347249.Hotel-Information)

Wilton

10/10

Exceptional

(11 reviews)

"Very nice property"

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

Nick

CA $217

CA $391 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Wilton-Hotels-Cottage-Beside-A-Waterfall.h114347249.Hotel-Information)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/9b2c42ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/ad9f4a52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/89a0b30d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/c66c8a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

[](https://www.expedia.ca/Rindge-Hotels-2-Bed.h88302089.Hotel-Information)

Rindge

10/10

Exceptional

(23 reviews)

"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."

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

Nicole B.

CA $207

CA $466 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Rindge-Hotels-2-Bed.h88302089.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/94000000/93400000/93397300/93397251/12a3ac85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/94000000/93400000/93397300/93397251/0f5f225a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93400000/93397300/93397251/6ecce540.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/94000000/93400000/93397300/93397251/c5b51bb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Cabin in a Rural Setting #16 near Temple,NH

[](https://www.expedia.ca/Temple-Hotels-Cozy-Cabin-In-A-Rural-Setting-16-Near-Temple.h93397251.Hotel-Information)

Temple

9.4/10

Exceptional

(17 reviews)

"The cabin was very clean and had everything you need for a few days. The location is perfect to go spend the day hiking and close enough to good restaurants, Milton's Pizza, Porter's and Ben's sugar shack that you can find great food."

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

Jon S.

CA $187

CA $313 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Temple-Hotels-Cozy-Cabin-In-A-Rural-Setting-16-Near-Temple.h93397251.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/25e52beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/6faf555f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/9396f37e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/e9dcc51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Finnish Cabin with Sauna on Lake Monomonac

[](https://www.expedia.ca/Rindge-Hotels-Finnish-Cabin-With-Sauna-On-Lake-Monomonac.h106476934.Hotel-Information)

Rindge

10/10

Exceptional

(11 reviews)

"Amazing place. We really enjoyed our brief stay. Great host. "

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

Gary S.

CA $205

CA $402 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Rindge-Hotels-Finnish-Cabin-With-Sauna-On-Lake-Monomonac.h106476934.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/105000000/104350000/104348200/104348182/1fa17254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104350000/104348200/104348182/df3a4490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104350000/104348200/104348182/f2388fcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/105000000/104350000/104348200/104348182/179827a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Cabin in a Rural setting-14

[](https://www.expedia.ca/Temple-Hotels-Cozy-Cabin-In-A-Rural-Setting-14.h104348182.Hotel-Information)

Temple

9.4/10

Exceptional

(8 reviews)

"Overall a nice stay!"

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

Jaymes R.

CA $171

CA $273 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Temple-Hotels-Cozy-Cabin-In-A-Rural-Setting-14.h104348182.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/3696f739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/67976cd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/1fd17ad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/8d109570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Adirondack Cabin with Sauna on Lake Monomonac

[](https://www.expedia.ca/Rindge-Hotels-Beautiful-Adirondack-Cabin-With-Sauna-On-Lake-Monomonac.h106335693.Hotel-Information)

Rindge

9.8/10

Exceptional

(25 reviews)

"This is a great property, and Jim is a wonderful host. He accommodated all our requests for sauna use and provided helpful tips about the area. We hope to return again one day!"

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

Leigh C.

CA $256

CA $507 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Rindge-Hotels-Beautiful-Adirondack-Cabin-With-Sauna-On-Lake-Monomonac.h106335693.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/114000000/113250000/113244100/113244057/1ee34890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/114000000/113250000/113244100/113244057/324c5fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113250000/113244100/113244057/f0a4aaca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113250000/113244100/113244057/38ded52f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi

[](https://www.expedia.ca/Greenfield-Hotels-Charming-Cabin-In-Delightful-Greenfield-New-Hampshire-With-WiFi-Access.h113244057.Hotel-Information)

Greenfield

9.8/10

Exceptional

(10 reviews)

"Its was great clean, quite and comfortable. "

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

John G.

CA $251

CA $360 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Greenfield-Hotels-Charming-Cabin-In-Delightful-Greenfield-New-Hampshire-With-WiFi-Access.h113244057.Hotel-Information)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/91000000/90710000/90703700/90703684/0ff8aab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90710000/90703700/90703684/87dfad16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer](https://images.trvl-media.com/lodging/91000000/90710000/90703700/90703684/5d0df046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/91000000/90710000/90703700/90703684/w1279h853x0y0-c309a337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Cabin in a rural setting (#10) In Temple, NH

[](https://www.expedia.ca/Temple-Hotels-Cozy-Cabin-In-A-Rural-Setting.h90703684.Hotel-Information)

Temple

9.0/10

Wonderful

(19 reviews)

"Nice little cabin, clean other cabins are a little close other than that everything was fine "

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

Lisa G.

CA $161

CA $280 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Temple-Hotels-Cozy-Cabin-In-A-Rural-Setting.h90703684.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/98000000/97010000/97004400/97004400/fc080d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/98000000/97010000/97004400/97004400/2745dbcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/98000000/97010000/97004400/97004400/aea2bcfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97010000/97004400/97004400/ed7fc300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

[](https://www.expedia.ca/Westminster-Hotels-Our-Pondside-Cabin-A-Charming-Retreat-With-Modern-Amenities-Near-Wachusett-Mtn.h97004400.Hotel-Information)

Westminster

10/10

Exceptional

(24 reviews)

"Our family stayed at the house for 2 nights to attend a nearby wedding. The house was just as pictured - lovely, clean, and perfect for our stay. The hosts have been very thoughtful about every detail from easy check-in to a well stocked kitchen to cozy blankets for the comfy couch. We had a wonderful time and highly recommend! "

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

Kelly G.

CA $305

CA $702 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Westminster-Hotels-Our-Pondside-Cabin-A-Charming-Retreat-With-Modern-Amenities-Near-Wachusett-Mtn.h97004400.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114490000/114487600/114487594/w906h683x59y0-02edd292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114490000/114487600/114487594/b5f81a63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114490000/114487600/114487594/w904h683x60y0-a89fabde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114490000/114487600/114487594/09fa9c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Room overlooking the waterfall

[](https://www.expedia.ca/Wilton-Hotels-River-Room-Overlooking-The-Waterfall.h114487594.Hotel-Information)

Wilton

10/10

Exceptional

(3 reviews)

"Had a great time, the grounds are spectacular with the river waterfall in the background. The Bathroom was stunning. Had everything we needed. The bed was super comfy too. The screened-in porch was convenient, too."

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

Romie G.

CA $217

CA $391 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Wilton-Hotels-River-Room-Overlooking-The-Waterfall.h114487594.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/5dd08019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/53ea3769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/94d9ae76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/303ca4c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grey Cabin with Sauna on Lake Monomonac

[](https://www.expedia.ca/Rindge-Hotels-Grey-Cabin-With-Sauna-On-Lake-Monomonac.h106489950.Hotel-Information)

Rindge

7.6/10

Good

(4 reviews)

"Great location host was on it.anything u needed he was there.no ac was the only thing.but it was unusally hot.i would go again"

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

Brian

CA $206

CA $446 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Rindge-Hotels-Grey-Cabin-With-Sauna-On-Lake-Monomonac.h106489950.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/fb54d968.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/8c094e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/06a81bab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/57c0c927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

[](https://www.expedia.ca/Peterborough-Hotels-Studio-Apt-With-Full-Kitchen-1-Minute-Stroll-Over-Picturesque-Bridge-Into-Town.h102238328.Hotel-Information)

Peterborough

9.8/10

Exceptional

(31 reviews)

"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"

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

Mark

CA $110

CA $222 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Peterborough-Hotels-Studio-Apt-With-Full-Kitchen-1-Minute-Stroll-Over-Picturesque-Bridge-Into-Town.h102238328.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/98000000/97320000/97317700/97317603/31e9eac5.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)

![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)

### Modern Downtown 12ppl Hot Tub Fire Pit Games

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

Keene

9.6/10

Exceptional

(22 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 $203

CA $418 total

includes taxes & fees

Feb 26 - Feb 27

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

![Exterior](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/f2b21706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/5d550d48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/bf758959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/88c9bc33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy & Bright Guest Suite

[](https://www.expedia.ca/Peterborough-Hotels-Cozy-Bright-Guest-Suite.h125299924.Hotel-Information)

Peterborough

CA $108

CA $259 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Peterborough-Hotels-Cozy-Bright-Guest-Suite.h125299924.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/123000000/122250000/122242200/122242101/70984371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122250000/122242200/122242101/2c3f1377.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/123000000/122250000/122242200/122242101/0b77f63f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/123000000/122250000/122242200/122242101/9133e4a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School

[](https://www.expedia.ca/Wilton-Hotels-Spacious-Historic-2-Bed-5-Min-Drive-To-High-Mowing.h122242101.Hotel-Information)

Wilton

10/10

Exceptional

(3 reviews)

"Wonderful and thoughtful hosts that went above and beyond to make us feel at home. We appreciated the coziness of the house and your kindness. "

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

Kadie H.

CA $220

CA $481 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Wilton-Hotels-Spacious-Historic-2-Bed-5-Min-Drive-To-High-Mowing.h122242101.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)

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

![Exterior detail](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/0113e9e7.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)

### Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

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

Keene

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 $286

CA $688 total

includes taxes & fees

Feb 16 - Feb 17

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

![Dining](https://images.trvl-media.com/lodging/123000000/122980000/122979900/122979859/0defd94d.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)

![TV, foosball, table tennis, books](https://images.trvl-media.com/lodging/123000000/122980000/122979900/122979859/c8f62078.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW! Cushing Home | Family Cabin Near Wachusett Mtn

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

Ashburnham

CA $424

CA $1,148 total

includes taxes & fees

Feb 13 - Feb 14

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

![Private kitchen](https://images.trvl-media.com/lodging/126000000/125510000/125509100/125509057/c518608e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125510000/125509100/125509057/567302b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125510000/125509100/125509057/049fd1c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/126000000/125510000/125509100/125509057/fe0b5860.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large 3BR Apartment in Marlborough NH: Sleeps 8-10: Close to Keene!

[](https://www.expedia.ca/Marlborough-Hotels-Large-3BR-Apartment-In-Marlborough-NH-Sleeps-8-10-Close-To-Keene.h125509057.Hotel-Information)

Marlborough

CA $190

CA $482 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Marlborough-Hotels-Large-3BR-Apartment-In-Marlborough-NH-Sleeps-8-10-Close-To-Keene.h125509057.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=2026-02-25&endDate=2026-02-26&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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CABIN)

Cottages

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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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=VACATION_HOME)

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## Top Winchendon Hotel Reviews

![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

"Good "

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

"Amazing staff and very clear rooms "

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

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

### Chocksett Inn and Restaurant

10/10 Excellent

"Updated rooms, clean throughout. Staff were welcoming. "

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

"Amazing breakfast "

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

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

### The Colonial Hotel

10/10 Excellent

"What's clean staff was friendly food was good bar was nice the buildings a little bit old "

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

![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg)

### Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"Reasonably priced and clean."

[](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.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

"Clean room. Comfortable bed. Quiet. Nice breakfast."

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

![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)

## Find out more about Winchendon

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winchendon. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Winchendon ](https://expedia.ca/Winchendon-Private-Vacation-Homes.d3000441689-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Winchendon ](https://expedia.ca/Winchendon-Cottages.d3000441689-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Winchendon ](https://expedia.ca/Winchendon-Apartments.d3000441689-aaApartments.Travel-Guide-Accommodation)
- [Cabin Rentals in Winchendon ](https://expedia.ca/Winchendon-Cabins.d3000441689-aaCabins.Travel-Guide-Accommodation)
- [Farmstay in Winchendon ](https://expedia.ca/Winchendon-Agritourism.d3000441689-aaAgritourism.Travel-Guide-Accommodation)
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- [Chalets in Winchendon ](https://expedia.ca/Winchendon-Chalets.d3000441689-aaChalets.Travel-Guide-Accommodation)
- [Lodges in Winchendon ](https://expedia.ca/Winchendon-Lodges.d3000441689-aaLodges.Travel-Guide-Accommodation)
- [Villas in Winchendon ](https://expedia.ca/Winchendon-Villas.d3000441689-aaVillas.Travel-Guide-Accommodation)
- [Motels in Winchendon ](https://expedia.ca/Winchendon-Motels.d3000441689-aaMotels.Travel-Guide-Accommodation)
- [Resorts in Winchendon ](https://expedia.ca/Winchendon-Resort-Hotels.d3000441689-aaResortHotels.Travel-Guide-Accommodation)
- [Inns in Winchendon ](https://expedia.ca/Winchendon-Inns.d3000441689-aaInns.Travel-Guide-Accommodation)
- [Guest Houses in Winchendon ](https://expedia.ca/Winchendon-Guest-Houses.d3000441689-aaGuestHouses.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Winchendon?

### What are some of the best vacation rentals that Winchendon has to offer?

### How many vacation rentals will I find in Winchendon?

### What’s there to see and do in Winchendon?

### What’s a vacation rental in Winchendon like?

### Expedia's Latest Trends

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Flights

- [Cheap Flights to Springfield](https://expedia.ca/Cheap-Flights-To-Springfield.d6047669.Travel-Guide-Flights)

Cars

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## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app