Title: Winchendon Vacation Rentals from $154: Search Short-Term Rentals | Expedia.com

[Winchendon Travel Guide](https://expedia.com/Winchendon.dx3000441689)[Hotels in Winchendon](https://expedia.com/Winchendon-Hotels.d3000441689.Travel-Guide-Hotels)[Flights to Winchendon](https://expedia.com/Cheap-Flights-To-Winchendon.d3000441689.Travel-Guide-Flights)[Car Rentals in Winchendon](https://expedia.com/Car-Rentals-In-Winchendon.d3000441689.Car-Rental-Guide)[Winchendon Vacation Packages](https://expedia.com/Winchendon.d3000441689.Destination-Travel-Guides)

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

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=3000441689&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/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 three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=3000441689&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=3000441689&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winchendon%2C+Massachusetts%2C+United+States+of+America&regionId=3000441689&latLong=42.685719%2C-72.044746&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=APARTMENT)

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## Top Winchendon Hotel Reviews

![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 and the staff was friendly. "

[](https://expedia.com/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.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

"Me and my family is so proud with our stay "

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

"The room was spotless, well-appointed with amenities. The staff was courteous and helpful. Outside access doors were proximal to parking. Dog friendly by observation. Coffee available 24 hr/day. Good breakfast selection.21st century charm and comfort at a good price."

[](https://expedia.com/Keene-Hotels-Holiday-Inn-Express-Keene.h14439.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

"Perfect "

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

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

### Doubletree by Hilton Hotel Leominster

10/10 Excellent

"Everything was great"

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

![The Burrell House](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/3cda440a_y.jpg)

### The Burrell House

10/10 Excellent

"The room was clean and comfortable. Within walking distance to Keene downtown. "

[](https://expedia.com/Keene-Hotels-The-Burrell-House.h72611296.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

"Great "

[](https://expedia.com/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.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, comfortable. "

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

"Although we had to cancel our reservation, everyone we spoke with on the telephone was professional, understanding, and kind."

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

## Find out more about Winchendon

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

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchendon vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Winchendon vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchendon in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $154 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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

At Expedia, we put the best Winchendon vacation 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 vacation.

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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- All accommodation types in Winchendon

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- [Vacation Homes in Winchendon ](https://expedia.com/Winchendon-Private-Vacation-Homes.d3000441689-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Winchendon ](https://expedia.com/Winchendon-Cottages.d3000441689-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Winchendon ](https://expedia.com/Winchendon-Apartments.d3000441689-aaApartments.Travel-Guide-Accommodation)
- [Cabin Rentals in Winchendon ](https://expedia.com/Winchendon-Cabins.d3000441689-aaCabins.Travel-Guide-Accommodation)
- [Farmstay in Winchendon ](https://expedia.com/Winchendon-Agritourism.d3000441689-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Winchendon ](https://expedia.com/Winchendon-Bed-And-Breakfast.d3000441689-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Chalets in Winchendon ](https://expedia.com/Winchendon-Chalets.d3000441689-aaChalets.Travel-Guide-Accommodation)
- [Lodges in Winchendon ](https://expedia.com/Winchendon-Lodges.d3000441689-aaLodges.Travel-Guide-Accommodation)
- [Villas in Winchendon ](https://expedia.com/Winchendon-Villas.d3000441689-aaVillas.Travel-Guide-Accommodation)
- [Motels in Winchendon ](https://expedia.com/Winchendon-Motels.d3000441689-aaMotels.Travel-Guide-Accommodation)
- [Resorts in Winchendon ](https://expedia.com/Winchendon-Resorts.d3000441689-aaResorts.Travel-Guide-Accommodation)
- [Inns in Winchendon ](https://expedia.com/Winchendon-Inns.d3000441689-aaInns.Travel-Guide-Accommodation)
- [Guest Houses in Winchendon ](https://expedia.com/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

Hotels

- [Amherst Hotels](https://expedia.com/Amherst-Hotels.d5948.Travel-Guide-Hotels)
- [Springfield Hotels](https://expedia.com/Springfield-Hotels.d6047669.Travel-Guide-Hotels)
- [Chatham Hotels](https://expedia.com/Chatham-Hotels.d10743.Travel-Guide-Hotels)
- [Fall River Hotels](https://expedia.com/Fall-River-Hotels.d6057.Travel-Guide-Hotels)
- [Foxborough Hotels](https://expedia.com/Foxborough-Hotels.d8136.Travel-Guide-Hotels)
- [Hyannis Hotels](https://expedia.com/Hyannis-Hotels.d1544.Travel-Guide-Hotels)
- [Provincetown Hotels](https://expedia.com/Provincetown-Hotels.d2909.Travel-Guide-Hotels)
- [Plymouth Hotels](https://expedia.com/Plymouth-Hotels.d9512.Travel-Guide-Hotels)
- [Newburyport Hotels](https://expedia.com/Newburyport-Hotels.d8938.Travel-Guide-Hotels)
- [South Yarmouth Hotels](https://expedia.com/South-Yarmouth-Hotels.d7627.Travel-Guide-Hotels)
- [Lowell Hotels](https://expedia.com/Lowell-Hotels.d8422.Travel-Guide-Hotels)
- [Brockton Hotels](https://expedia.com/Brockton-Hotels.d7068.Travel-Guide-Hotels)
- [Nantucket Hotels](https://expedia.com/Nantucket-Hotels.d285.Travel-Guide-Hotels)
- [West Springfield Hotels](https://expedia.com/West-Springfield-Hotels.d7738.Travel-Guide-Hotels)
- [Rockport Hotels](https://expedia.com/Rockport-Hotels.d6350.Travel-Guide-Hotels)
- [Northampton Hotels](https://expedia.com/Northampton-Hotels.d9187.Travel-Guide-Hotels)
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Cars

- [Car rentals in Mansfield](https://expedia.com/Car-Rentals-In-Mansfield.d8456.Car-Rental-Guide)
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Activities

- [Things to do in Hyannis](https://expedia.com/Things-To-Do-In-Hyannis.d1544.Travel-Guide-Activities)

Packages

- [Trip to Nantucket](https://expedia.com/Nantucket.d285.Destination-Travel-Guides)

Vacation Rentals

- [Vacation Rentals Nantucket](https://expedia.com/Nantucket-Vacation-Rentals.d285.Travel-Guide-VacationRentals)

General

- [Visit Manchester-by-the-Sea](https://expedia.com/Manchester-By-The-Sea.dx129363)
- [Visit Rockport](https://expedia.com/Rockport.dx6350)

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