Winchendon Vacation Rentals from $145: Search Short-Term Rentals

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

Cozy Lakefront Cottage : Visitors give good reviews to this Winchendon vacation home rental, which is located on a lake and has a patio, a garden, and a barbecue grill 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 vacation with amenities like a selection of books.

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Our top choices for Winchendon vacation 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.

$341 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

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

Peterborough

Basmattee B.

$134 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern living room with a flat-screen TV mounted on a wall, a wooden entertainment center, a yellow sofa, and a kitchen area with white cabinetry.

3. Fresh & Modern 4BR - 2 Baths + Parking

Fitchburg

$337 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

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

Temple

Ann S.

$180 nightly

Nov 11 - Nov 12

Total with taxes and fees

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.

$273 nightly

Dec 1 - Dec 2

Total with taxes and fees

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

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

Temple

Dean S.

$194 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

7. Cottage beside a waterfall

Wilton

Shane

$246 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

8. Cozy Cabin in a Rural setting-14

Temple

Anghy

$216 nightly

Nov 9 - Nov 10

Total with taxes and fees

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.

9. Spacious 2 bedroom sanctuary in the heart of Fitchburg

Fitchburg

$133 nightly

Nov 13 - Nov 14

Total with taxes and fees

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

10. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

Rindge

Susan G.

$337 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

11. "Pondlife" - Waterfront home in a peaceful, wooded setting.

Fitzwilliam

Margaret

$253 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

12. Fitchburg hideaway Home

Fitchburg

$211 nightly

Nov 16 - Nov 17

Total with taxes and fees

13. Cozy Cabin in a Rural setting #8

Temple

James M.

$170 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

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

Westminster

Shreya

$435 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

15. River Room overlooking the waterfall

Wilton

Bob H.

$246 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

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

Temple

fran f.

$231 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

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

Dublin

David W.

$272 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

18. Cozy & Stylish 2-bedroom Home in Leominster

Leominster

$196 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

19. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Keene

cody s.

$321 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

20. Cobb Meadow House: Cozy 5 Bedroom Retreat

Dublin

Veronique S.

$628 nightly

Nov 9 - Nov 10

Total with taxes and fees

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Top Winchendon Hotel Reviews

A covered porch with Adirondack chairs and a table with wine glasses, overlooking a lake and lush greenery.

The Maguire House Bed & Breakfast

Ashburnham

10/10 Excellent

Anonymous traveler

A grand lobby with a staircase, a piano, comfortable seating, and large windows.

The Colonial Hotel

Gardner

10/10 Excellent

Robin

A well-lit garden area with a gazebo, a small house, and a large tree in the background.

Howarth House B&B

Fitchburg

10/10 Excellent

For the wedding we stayed at our very first B&B. Howarth House Bed and Breakfast in Fitchburg, Mass. It is a beautiful house built in 1910. The current owners, Sarah and Ryan purchased the house in 2020. The owners were friendly, kind, accommodating and Ryan can sure cook a great breakfast. Sarah presented us with a departing gift of her homemade Blueberry and white chocolate scones. Delicious! The room was comfortable, the location quiet and we will definitely be back. I wish I had taken more...

Darleen

A hotel lobby with a central circular skylight, a reception desk, and a seating area with sofas.

Doubletree by Hilton Hotel Leominster

Leominster

10/10 Excellent

Paola

A dining area with wooden tables and chairs, a mural on the wall, and large windows.

The Birchwood Inn

Temple

10/10 Excellent

Anonymous traveler

A wooden table set with plates, cutlery, and a folded napkin.

The Carriage Barn Inn

Keene

10/10 Excellent

Richard

A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

Hampton Inn & Suites Keene

Keene

10/10 Excellent

kristin

A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

Keene Elm City Hotel, an Ascend Collection Hotel

Keene

10/10 Excellent

Kristine

A two-story house with a red door, green shutters, and a snow-covered front yard.

Centennial House

Northfield

10/10 Excellent

My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne

Anonymous traveler

A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.

Best Western Plus Keene Hotel

Keene

10/10 Excellent

Susan

A room with a fireplace, a large mirror, and a window with a view of the outside.

Chocksett Inn and Restaurant

Sterling

10/10 Excellent

Bryan

A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.

Courtyard by Marriott Keene Downtown

Keene

10/10 Excellent

Vic

A two-story building with a white facade and green shutters, a covered front porch, and a sign for the "M" Inn.

Monadnock Inn

Jaffrey

10/10 Excellent

On a Foliage tour through New England in October, my wife and I stayed at The Monadnock Inn following a hike of the nearby Mt. Monadnock. Arrival mid-week was simple and the Inn is full of centuries-old charm and comfort. Check-in was very simple and we were handed a key and walked up the stairs to the 3rd Floor Pauline Room. The room was very cozy with an antique soak tub and shower (great after a long hike), beautiful bay windows, steam radiator, comfortable bed, and warmly lit. There was no...

Todd

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 $145 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.

Frequently Asked Questions

Are there vacation rentals in Winchendon?

Yes, we offer vacation rentals in Winchendon near The Robinson-Broadhurst Foundation Performing Arts Ampitheater, or you can choose a secluded option if you're looking for extra privacy while you relax. Winchendon is known for its parks.

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

Cozy Lakefront Cottage: Visitors give good reviews to this Winchendon vacation home rental, which is located on a lake and has a patio, a garden, and a barbecue grill 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 vacation with amenities like a selection of books.

How many vacation rentals will I find in Winchendon?

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

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 vacation rental in Winchendon like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Winchendon. Vacation rentals offer extras such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.

Winchendon Vacation Rentals

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Upfront pricing

Check prices for these dates

Our top choices for Winchendon vacation rentals

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

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

3. Fresh & Modern 4BR - 2 Baths + Parking

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

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

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

7. Cottage beside a waterfall

8. Cozy Cabin in a Rural setting-14

9. Spacious 2 bedroom sanctuary in the heart of Fitchburg

10. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

11. "Pondlife" - Waterfront home in a peaceful, wooded setting.

12. Fitchburg hideaway Home

13. Cozy Cabin in a Rural setting #8

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

15. River Room overlooking the waterfall

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

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

18. Cozy & Stylish 2-bedroom Home in Leominster

19. Modern Downtown Escape HotTub Fire Pit Games 12ppl

20. Cobb Meadow House: Cozy 5 Bedroom Retreat

Find vacation rentals that suit your style

Top Winchendon Hotel Reviews

The Maguire House Bed & Breakfast

10/10 Excellent

Find out more about Winchendon

Everything you need to know about Winchendon vacation rentals

Winchendon vacation rentals: An excellent choice for every season

How to find incredible deals on Winchendon rentals

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?

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