Title: Winchendon Vacation Rentals from CA $221: 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

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two 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)

In three months

[Jul 3 - Jul 5](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 31 - Aug 2](https://www.expedia.ca/Hotel-Search?regionId=3000441689&startDate=2026-07-31&endDate=2026-08-02&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

![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)

![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)

![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 $549

CA $728 total

includes taxes & fees

Apr 8 - Apr 9

[](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)

![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)

![Interior](https://images.trvl-media.com/lodging/115000000/114350000/114347300/114347249/2569f54f.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)

### Cottage beside a waterfall

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

Wilton

10/10

Exceptional

(12 reviews)

"BEAUTIFUL surroundings and very peaceful. Would definitely recommend staying here!! "

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

Vicki L.

CA $223

CA $405 total

includes taxes & fees

Apr 8 - Apr 9

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

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/6c4ecd64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/e7a2f4c6.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)

### Cabin & Sauna on Lake Monomonac near Mt. Monadnock

[](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 $291

CA $461 total

includes taxes & fees

Apr 8 - Apr 9

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

![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)

![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)

### 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)

"Place was a very nice stay, area was close to nice places."

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

Rui V.

CA $176

CA $280 total

includes taxes & fees

Apr 8 - Apr 9

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

![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)

![Exterior](https://images.trvl-media.com/lodging/94000000/93400000/93397300/93397251/0f5f225a.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

(18 reviews)

"Amazing place very happy will stay again 10 stars "

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

Dean S.

CA $192

CA $322 total

includes taxes & fees

Apr 8 - Apr 9

[](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/92000000/91900000/91892000/91891970/544c6c17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91900000/91892000/91891970/050c1d5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/92000000/91900000/91892000/91891970/8e772eed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91900000/91892000/91891970/bace89a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

[](https://www.expedia.ca/Westminster-Hotels-Lakefront-At-Base-Of-Ski-Resort.h91891970.Hotel-Information)

Westminster

9.6/10

Exceptional

(30 reviews)

"Cutest home! My family loved it! "

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

Shanna D.

CA $209

CA $604 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Westminster-Hotels-Lakefront-At-Base-Of-Ski-Resort.h91891970.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)

![Interior](https://images.trvl-media.com/lodging/114000000/113250000/113244100/113244057/cb8c986c.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)

![Living area](https://images.trvl-media.com/lodging/114000000/113250000/113244100/113244057/324c5fbd.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

10/10

Exceptional

(15 reviews)

"Charming location and beautiful setting. "

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

Cherie G.

CA $257

CA $367 total

includes taxes & fees

Apr 8 - Apr 9

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

(27 reviews)

"Great family spot. Very clean and comfortable. Convenient to local attractions and shopping. "

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

Dennyse M.

CA $313

CA $716 total

includes taxes & fees

Apr 12 - Apr 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)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114490000/114487600/114487594/09fa9c50.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)

### 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 $223

CA $405 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Wilton-Hotels-River-Room-Overlooking-The-Waterfall.h114487594.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/c6092f96.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/107000000/106480000/106477000/106476934/6faf555f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin & Sauna on Lake Monomonac near Mt. Monadnock

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

Rindge

10/10

Exceptional

(12 reviews)

"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "

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

Rebecca

CA $228

CA $367 total

includes taxes & fees

Apr 8 - Apr 9

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

![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)

![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/89000000/88310000/88302100/88302089/18e29612.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 $232

CA $500 total

includes taxes & fees

Apr 13 - Apr 14

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

![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/98000000/97320000/97317700/97317603/89c4c4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/d85bd4e5.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)

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

[](https://www.expedia.ca/Keene-Hotels-Modern-Downtown-12ppl-Hot-Tub-Fire-Pit-Games.h97317603.Hotel-Information)

Keene

9.6/10

Exceptional

(22 reviews)

"Nice house in a nice location. "

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

Rob B.

CA $189

CA $406 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Keene-Hotels-Modern-Downtown-12ppl-Hot-Tub-Fire-Pit-Games.h97317603.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/107000000/106490000/106490000/106489950/14aa4f5f.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)

### Cabin & Sauna on Lake Monomonac near Mt. Monadnock

[](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 $249

CA $409 total

includes taxes & fees

Apr 19 - Apr 20

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

![Exterior](https://images.trvl-media.com/lodging/91000000/90710000/90703700/90703684/1335ce74.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)

![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 $154

CA $274 total

includes taxes & fees

Apr 18 - Apr 19

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

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/e861780f.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

(33 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 $106

CA $221 total

includes taxes & fees

Apr 13 - Apr 14

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

![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)

![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)

### Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

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

Dublin

10/10

Exceptional

(26 reviews)

"Good place to stay during a wedding week"

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

Veronique S.

CA $584

CA $1,014 total

includes taxes & fees

Apr 8 - Apr 9

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

![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)

![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)

### 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)

"Host was wonderful and very accommodating! Home was very welcoming and comfortable. Highly recommend!"

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

Robin Q.

CA $282

CA $562 total

includes taxes & fees

Apr 12 - Apr 13

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

![Exterior](https://images.trvl-media.com/lodging/127000000/126960000/126954700/126954614/0e552df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/127000000/126960000/126954700/126954614/c44f994b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/127000000/126960000/126954700/126954614/b438235e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/127000000/126960000/126954700/126954614/d485dbea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 Cabins & Sauna on Lake Monomonac

[](https://www.expedia.ca/Rindge-Hotels-2-Cabins-Sauna-On-Lake-Monomonac.h126954614.Hotel-Information)

Rindge

CA $750

CA $1,100 total

includes taxes & fees

Apr 19 - Apr 20

[](https://www.expedia.ca/Rindge-Hotels-2-Cabins-Sauna-On-Lake-Monomonac.h126954614.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/110000000/109200000/109193700/109193661/e89dbf4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109200000/109193700/109193661/639c69b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109200000/109193700/109193661/c1277686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109200000/109193700/109193661/9914171c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3 Cabins/Houses and Sauna on Lake Monomonac near Mt. Monadnock

[](https://www.expedia.ca/Rindge-Hotels-3-CabinsHouses-And-Sauna-On-Lake-Monomonac-Near-Mt-Monadnock.h109193661.Hotel-Information)

Rindge

CA $938

CA $1,505 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Rindge-Hotels-3-CabinsHouses-And-Sauna-On-Lake-Monomonac-Near-Mt-Monadnock.h109193661.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)

![Interior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/4e846ae7.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 $267

CA $669 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Keene-Hotels-The-Leverett-House-In-Charming-Keene.h117913271.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=2026-04-21&endDate=2026-04-22&regionId=3000441689&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

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=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VACATION_HOME)

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=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=COTTAGE)

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=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CABIN)

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=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APARTMENT)

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=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CONDO)

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## Top Winchendon Hotel Reviews

![Great Wolf Lodge Boston / Fitchburg, MA](https://images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/08aa09e5_y.jpg)

### Great Wolf Lodge Boston / Fitchburg, MA

6/10 Okay

"Yes but the room is a lot dusk"

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

![Hampton Inn & Suites Keene](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/f95623cd_y.jpg)

### Hampton Inn & Suites Keene

10/10 Excellent

"The front desk staff was exceptional! Very friendly and accommodating!"

[](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/4000000/3880000/3878900/3878809/94272c61_y.jpg)

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

10/10 Excellent

"Always dependable, comfortable, clean rooms and friendly staff."

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

"Great hotel for a weekend getaway. Very walkable neighborhood too!"

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

![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca_y.jpg)

### Best Western Plus Keene Hotel

10/10 Excellent

"Nice place"

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

![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/ad889baf_y.jpg)

### The Colonial Hotel

8/10 Good

"Bathroom should have a safety grab bar in the shower as well as hooks for towels."

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

![The Burrell House](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/a0cdde49_y.jpg)

### The Burrell House

10/10 Excellent

"The room was very nice and quaint. We loved the location. It was so quick and easy to walk to downtown Keene. We had to rent a cot to make it accommodate 3 people. I guess we had missed the fine print in the Expedia listing that said it would work for 3 if a cot was added. The building felt secure and was well taken care of. We’d consider staying here again if we return to the area. "

[](https://expedia.ca/Keene-Hotels-The-Burrell-House.h72611296.Hotel-Information)

![Motel 6 Leominster, MA](https://images.trvl-media.com/lodging/1000000/1000000/996200/996152/e5860404_y.jpg)

### Motel 6 Leominster, MA

10/10 Excellent

"It's fine for the price. Clean and functional."

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

![Econo Lodge](https://images.trvl-media.com/lodging/2000000/1210000/1202500/1202406/636b63b9_y.jpg)

### Econo Lodge

10/10 Excellent

"Very clean comfortable a in d staff was excellent "

[](https://expedia.ca/Westminster-Hotels-Econo-Lodge.h1202406.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)
- [Apartments in Winchendon ](https://expedia.ca/Winchendon-Apartments.d3000441689-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Winchendon ](https://expedia.ca/Winchendon-Cottages.d3000441689-aaCottages.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)
- [B&B in Winchendon ](https://expedia.ca/Winchendon-Bed-And-Breakfast.d3000441689-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Lodges in Winchendon ](https://expedia.ca/Winchendon-Lodges.d3000441689-aaLodges.Travel-Guide-Accommodation)
- [Chalets in Winchendon ](https://expedia.ca/Winchendon-Chalets.d3000441689-aaChalets.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)
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- [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?

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

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- [Car rentals in Halifax](https://expedia.ca/Car-Rentals-In-Halifax.d6139204.Car-Rental-Guide)

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- [Halifax Vacations](https://expedia.ca/Halifax.d6139204.Destination-Travel-Guides)
- [Nantucket Vacations](https://expedia.ca/Nantucket.d285.Destination-Travel-Guides)

General

- [Visit Great Barrington](https://expedia.ca/Great-Barrington.dx110336)
- [Visit Worcester](https://expedia.ca/Worcester.dx6023336)
- [Visit Shelburne Falls](https://expedia.ca/Shelburne-Falls.dx6294302)
- [Visit Rockport](https://expedia.ca/Rockport.dx6350)
- [Visit Centerville](https://expedia.ca/Centerville.dx88031)
- [Visit Nantucket](https://expedia.ca/Nantucket.dx285)
- [Visit Dennis Port](https://expedia.ca/Dennis-Port.dx6665)
- [Visit Manchester-by-the-Sea](https://expedia.ca/Manchester-By-The-Sea.dx129363)

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