Title: Holiday Rentals Winchendon from £198: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

[Winchendon Travel Guide](https://expedia.co.uk/Winchendon.dx3000441689)[Hotels in Winchendon](https://expedia.co.uk/Winchendon-Hotels.d3000441689.Travel-Guide-Hotels)[Winchendon Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchendon.d3000441689.Car-Hire-Guide)[Winchendon Holidays](https://expedia.co.uk/Winchendon.d3000441689.Holidays-City-Breaks)

![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

[20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=3000441689&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=3000441689&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[1 May - 3 May](https://www.expedia.co.uk/Hotel-Search?regionId=3000441689&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=3000441689&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchendon holiday 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)

![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)

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

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

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

Ashburnham

£265

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/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)

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

£374

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/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)

![Dining](https://images.trvl-media.com/lodging/115000000/114350000/114347300/114347249/32163bc8.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)

### Cottage beside a waterfall

[](https://www.expedia.co.uk/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

£215

includes taxes & fees

9 Feb - 10 Feb

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

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

![Private kitchen](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/94e00bfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy & Bright Guest Suite

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

Peterborough

£142

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Peterborough-Hotels-Cozy-Bright-Guest-Suite.h125299924.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)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104350000/104348200/104348182/w1277h850x0y0-2b21b4c5.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)

![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.co.uk/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.

£151

includes taxes & fees

9 Feb - 10 Feb

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

![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)

![Hair dryer](https://images.trvl-media.com/lodging/91000000/90710000/90703700/90703684/5d0df046.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)

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

[](https://www.expedia.co.uk/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.

£155

includes taxes & fees

18 Feb - 19 Feb

[](https://www.expedia.co.uk/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)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/57c0c927.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)

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

[](https://www.expedia.co.uk/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

£102

includes taxes & fees

9 Feb - 10 Feb

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

![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)

![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)

### River Room overlooking the waterfall

[](https://www.expedia.co.uk/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.

£215

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Wilton-Hotels-River-Room-Overlooking-The-Waterfall.h114487594.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)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/94000000/93400000/93397300/93397251/629b3c49.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.co.uk/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.

£173

includes taxes & fees

9 Feb - 10 Feb

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

![Property grounds](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/89a0b30d.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)

![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.co.uk/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.

£250

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Rindge-Hotels-2-Bed.h88302089.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/107000000/106480000/106477000/106476934/9396f37e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/450474c7.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)

### Finnish Cabin with Sauna on Lake Monomonac

[](https://www.expedia.co.uk/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.

£219

includes taxes & fees

9 Feb - 10 Feb

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

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

£198

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/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)

![Exterior](https://images.trvl-media.com/lodging/98000000/97010000/97004400/97004400/aea2bcfd.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)

![3 bedrooms, travel cot, 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.co.uk/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.

£377

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/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/107000000/106490000/106490000/106489950/56fde17e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/2bae6b8f.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)

![Lobby](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/920497ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grey Cabin with Sauna on Lake Monomonac

[](https://www.expedia.co.uk/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

£239

includes taxes & fees

9 Feb - 10 Feb

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

![Interior](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/0545aa58.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)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/d2180d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Adirondack Cabin with Sauna on Lake Monomonac

[](https://www.expedia.co.uk/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.

£292

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Rindge-Hotels-Beautiful-Adirondack-Cabin-With-Sauna-On-Lake-Monomonac.h106335693.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/b4c71f0d.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)

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

[](https://www.expedia.co.uk/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.

£227

includes taxes & fees

26 Feb - 27 Feb

[](https://www.expedia.co.uk/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.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)

![2 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/123000000/122250000/122242200/122242101/0b77f63f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122250000/122242200/122242101/2c0325d5.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.co.uk/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.

£257

includes taxes & fees

15 Feb - 16 Feb

[](https://www.expedia.co.uk/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)

![Interior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/e0a6d5c3.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)

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

[](https://www.expedia.co.uk/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.

£374

includes taxes & fees

9 Feb - 10 Feb

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

![Property grounds](https://images.trvl-media.com/lodging/118000000/117030000/117026300/117026212/081b1dd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117030000/117026300/117026212/fd5b30e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117030000/117026300/117026212/46634a08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117030000/117026300/117026212/bd896670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Unique Cozy private 1-bedroom apartment in charming Temple

[](https://www.expedia.co.uk/Temple-Hotels-Unique-Cozy-Private-1-Bedroom-Apartment-In-Charming-Temple.h117026212.Hotel-Information)

Temple

9.8/10

Exceptional

(7 reviews)

"Our stay was great. I loved the apartment and wish we had been there longer to enjoy the outdoors as well."

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

Julia P.

£318

includes taxes & fees

12 Feb - 13 Feb

[](https://www.expedia.co.uk/Temple-Hotels-Unique-Cozy-Private-1-Bedroom-Apartment-In-Charming-Temple.h117026212.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)

![5 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/c4e70041.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.co.uk/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.

£851

includes taxes & fees

16 Feb - 17 Feb

[](https://www.expedia.co.uk/Dublin-Hotels-5-Bedroom-Cozy-New-England-Home-Cobb-Meadow-House.h74153605.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.co.uk/Hotel-Search?startDate=2026-02-22&endDate=2026-02-23&regionId=3000441689&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find holiday rentals that suit your style

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=APARTMENT)

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=COTTAGE)

Cabins

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CABIN)

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## Top Winchendon Hotel Reviews

![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.co.uk/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.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

"Great 😊 "

[](https://expedia.co.uk/Leominster-Hotels-Motel-6-Leominster.h996152.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

"Very good, we will return soon."

[](https://expedia.co.uk/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.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.co.uk/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.co.uk/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.co.uk/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.co.uk/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.co.uk/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.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.co.uk/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.Hotel-Information)

## Find out more about Winchendon

**Everything you need to know about** **Winchendon** **holiday rentals**

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchendon holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchendon holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Winchendon holiday rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Winchendon. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchendon holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Winchendon holiday rentals we have selected for you start as low as £198 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Winchendon rentals**

At Expedia, we put the best Winchendon holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchendon rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchendon holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchendon. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

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- [South Wales Holiday Rentals ](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals)
- [North Wales Holiday Rentals ](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals)
- [London Holiday Rentals ](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals)
- [York Holiday Rentals ](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals)
- [Blackpool Holiday Rentals ](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals)
- [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations)
- [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals)
- [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals)
- [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals)
- [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals)
- [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations)
- [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations)
- [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations)
- [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations)
- [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations)

## Frequently asked questions

### Are there holiday rentals in Winchendon?

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

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

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

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

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