Holiday Rentals Winchendon from £119: Find Short-Term Rentals & Holiday Accommodations

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

Cozy Lakefront Cottage : This highly rated holiday home rental in Winchendon is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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In two weeks

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Our top choices for Winchendon holiday rentals

A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

1. Enjoy your stay in an antique home in an antique toy museum!

Winchendon

Katja Z.

includes taxes & fees

9 Nov - 10 Nov

A sunlit room with a large window, a bench, and a sofa.

2. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

Rindge

Susan G.

includes taxes & fees

9 Nov - 10 Nov

A lake surrounded by trees, with a wooden deck leading to a white railing.

3. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

Fitzwilliam

Margaret

includes taxes & fees

9 Nov - 10 Nov

A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

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

Peterborough

Basmattee B.

includes taxes & fees

10 Nov - 11 Nov

A wooden fence with a rustic appearance, surrounded by lush greenery and purple flowers.

5. Two Bedroom Guesthouse near many attractions pet friendly with private deck

Gardner

Kristin R.

includes taxes & fees

1 Dec - 2 Dec

A stone pathway leading to a large, multi-story building surrounded by trees and shrubs.

6. Cottage beside a waterfall

Wilton

Shane

includes taxes & fees

9 Nov - 10 Nov

A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

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

Westminster

Shreya

includes taxes & fees

11 Nov - 12 Nov

A modern living room with a fireplace, a mounted TV, and a leather couch.

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

Temple

fran f.

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a wooden door, a sofa, a dining table with chairs, and a mounted TV.

9. Cozy Tiny House on Main Street. Fully Renovated.

Dublin

David W.

includes taxes & fees

9 Nov - 10 Nov

A small, single-story house with a front door open, revealing a kitchen area with a sink and cabinets.

10. Cozy Cabin in a rural setting #12 in Temple NH

Temple

Dean S.

includes taxes & fees

9 Nov - 10 Nov

A red house with a stone pathway leading to it, surrounded by autumn foliage.

11. Cobb Meadow House: Cozy 5 Bedroom Retreat

Dublin

Veronique S.

includes taxes & fees

9 Nov - 10 Nov

A modern hotel room with a large flat-screen TV mounted on a wooden wall, a bed with a white comforter, and a carpeted floor.

12. Spacious 2 bedroom sanctuary in the heart of Fitchburg

Fitchburg

includes taxes & fees

9 Nov - 10 Nov

A black-framed door with a glass panel, leading into a hallway with wooden flooring and white walls.

13. Cozy Cabin in a Rural setting-14

Temple

Anghy

includes taxes & fees

9 Nov - 10 Nov

A stone pathway leading to a rustic building with a steep roof, surrounded by autumn foliage and a stone wall.

14. River Room overlooking the waterfall

Wilton

Bob H.

includes taxes & fees

9 Nov - 10 Nov

A garden with a stone pathway, a wooden fence, and various plants.

15. Fitchburg hideaway Home

Fitchburg

includes taxes & fees

11 Nov - 12 Nov

A modern kitchen with a wooden countertop, dark cabinets, and a large window.

16. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Keene

cody s.

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with granite countertops, stainless steel appliances, and a central island.

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

Keene

Jeremy S.

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a bed, a bedside table, and a nightstand. There is a window with blinds and a door leading to the outside.

18. Cozy Cabin in a rural setting #10 In Temple, NH

Temple

Ann S.

includes taxes & fees

12 Nov - 13 Nov

A staircase with dark wooden steps and white handrails, leading to a door at the top.

19. Cozy & Stylish 2-bedroom Home in Leominster

Leominster

includes taxes & fees

9 Nov - 10 Nov

20. Cozy Cabin in a Rural setting #8

Temple

James M.

includes taxes & fees

9 Nov - 10 Nov

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Top Winchendon Hotel Reviews

Centennial House

10/10 Excellent

"A beautifully restored historic home. The Sturbridge room was quiet and perfect for a romantic getaway. David was very welcoming and friendly. The gazebo was a great place to watch the sunset."

Gardner Inn

10/10 Excellent

"Overall, a pleasant stay. The staff were very friendly and helpful. The room was clean, spacious and in order. The hotel provides a centrally located beverage area with free coffee and tea. There are several restaurants with walking distance and more just a short drive away. Convenient to the highway and numerous attractions. And very budget friendly."

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, cottages, apart-hotels, cabins, 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 £119 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.

Frequently asked questions

Are there holiday rentals in Winchendon?

Yes, there are holiday rentals in Winchendon close to The Robinson-Broadhurst Foundation Performing Arts Ampitheater, or you can select a more secluded option if you're looking for a relaxing stay. Winchendon is known for its parks.

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

Cozy Lakefront Cottage: This highly rated holiday home rental in Winchendon is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals will I find in Winchendon?

Choose from 6 Expedia holiday rentals in Winchendon for a memorable holiday.

What’s there to see and do in Winchendon?

Wendall P. Clark Memorial and Hyde Park are a couple of lovely local spots to get outside and enjoy nature. Lake Dennison State Recreation Area and Beals Memorial Library are other places to visit while you're in town.

What’s a holiday rental in Winchendon like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchendon. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip.

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Check prices for these dates

Our top choices for Winchendon holiday rentals

1. Enjoy your stay in an antique home in an antique toy museum!

2. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

3. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

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