A hilly landscape with a tower on top, dense forest, and a cloudy sky.

Winchendon Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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!

Enjoy your stay in an antique home in an antique toy museum!
Winchendon
9.4 out of 10, Exceptional, (10 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
Katja Z.
The price is AED 1,194
AED 1,359 total
includes taxes & fees
6 Nov - 7 Nov
Enjoy your stay in an antique home in an antique toy museum!
A sunlit room with a large window, a bench, and a sofa.

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

2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Rindge
10.0 out of 10, Exceptional, (25 reviews)
"Excellent property, really enjoyed this beautiful home."
United States
Susan G.
The price is AED 716
AED 1,375 total
includes taxes & fees
8 Nov - 9 Nov
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A lake surrounded by trees, with a wooden deck leading to a white railing.

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

"Pondlife" - Waterfront home in a peaceful, wooded setting.
Fitzwilliam
10.0 out of 10, Exceptional, (7 reviews)
"Pondlife was clean, calm, cozy, and peaceful...exactly what we wanted...fall foliage was gorgeous....rail trail hiking adjacent to the property and plenty of mountain hiking nearby. If you want to be immersed in nature's beauty, this is perfect..."
United States
Margaret
The price is AED 876
AED 1,034 total
includes taxes & fees
8 Nov - 9 Nov
"Pondlife" - Waterfront home in a peaceful, wooded setting.
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.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Peterborough
9.8 out of 10, Exceptional, (48 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is AED 317
AED 591 total
includes taxes & fees
10 Nov - 11 Nov
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A residential building with a wooden balcony and a window.

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

Two Bedroom Guesthouse near many attractions pet friendly with private deck
Gardner
10.0 out of 10, Exceptional, (3 reviews)
"Cute little guesthouse. Super clean and lovely decorated."
United States
Kristin R.
The price is AED 545
AED 1,143 total
includes taxes & fees
1 Dec - 2 Dec
Two Bedroom Guesthouse near many attractions pet friendly with private deck
A hammock set up between trees in a forested area with a rocky stream in the background.

6. Cottage beside a waterfall

Cottage beside a waterfall
Wilton
9.8 out of 10, Exceptional, (24 reviews)
"Welcome letter to cottage is rude! Nice little cottage. That’s about it! No instructions on checkout at all! Location is great! Highly recommend the Taco Time restaurant though in town!"
United States
Shane
The price is AED 588
AED 1,008 total
includes taxes & fees
6 Nov - 7 Nov
Cottage beside a waterfall
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

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Westminster
10.0 out of 10, Exceptional, (40 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is AED 826
AED 1,801 total
includes taxes & fees
11 Nov - 12 Nov
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
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

Cozy Cabin in a Rural Setting #16 near Temple,NH
Temple
9.4 out of 10, Exceptional, (28 reviews)
"Great place to stay. The cabin was nice and cozy. Quiet and remote area to relax"
United States
Anthony R.
The price is AED 611
AED 945 total
includes taxes & fees
8 Nov - 9 Nov
Cozy Cabin in a Rural Setting #16 near Temple,NH
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.

Cozy Tiny House on Main Street. Fully Renovated.
Dublin
10.0 out of 10, Exceptional, (5 reviews)
"This was a perfect place to stay for my solo trip into town for a family wedding. The host was incredibly responsive and friendly and I'd recommend this place to anyone visiting the area!"
United States
David W.
The price is AED 771
AED 1,100 total
includes taxes & fees
6 Nov - 7 Nov
Cozy Tiny House on Main Street. Fully Renovated.
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

Cozy Cabin in a rural setting #12 in Temple NH
Temple
9.0 out of 10, Wonderful, (26 reviews)
"Amazing best place in nh"
United States
Dean S.
The price is AED 480
AED 796 total
includes taxes & fees
8 Nov - 9 Nov
Cozy Cabin in a rural setting #12 in Temple NH
A red house with a stone pathway leading to it, surrounded by autumn foliage.

11. Cobb Meadow House: Cozy 5 Bedroom Retreat

Cobb Meadow House: Cozy 5 Bedroom Retreat
Dublin
10.0 out of 10, Exceptional, (27 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is AED 1,543
AED 2,518 total
includes taxes & fees
8 Nov - 9 Nov
Cobb Meadow House: Cozy 5 Bedroom Retreat
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

Spacious 2 bedroom sanctuary in the heart of Fitchburg
Fitchburg
The price is AED 456
AED 530 total
includes taxes & fees
8 Nov - 9 Nov
Spacious 2 bedroom sanctuary in the heart of Fitchburg
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

Cozy Cabin in a Rural setting-14
Temple
9.4 out of 10, Exceptional, (13 reviews)
"The experience was exemplary, and I would certainly consider staying at this property again should my travels return me to New Hampshire."
United States
Anghy
The price is AED 558
AED 885 total
includes taxes & fees
8 Nov - 9 Nov
Cozy Cabin in a Rural setting-14
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

River Room overlooking the waterfall
Wilton
10.0 out of 10, Exceptional, (7 reviews)
"Couldn't ask for a lovelier place to spend a couple of days in New Hampshire in May!"
United States
Bob H.
The price is AED 588
AED 1,008 total
includes taxes & fees
6 Nov - 7 Nov
River Room overlooking the waterfall
A modern living room with a sectional sofa, a coffee table, and a patterned rug.

15. Fitchburg hideaway Home

Fitchburg hideaway Home
Fitchburg
The price is AED 595
AED 849 total
includes taxes & fees
10 Nov - 11 Nov
Fitchburg hideaway Home
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

16. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is AED 757
AED 1,316 total
includes taxes & fees
9 Nov - 10 Nov
Modern Downtown Escape HotTub Fire Pit Games 12ppl
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!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
9.8 out of 10, Exceptional, (6 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is AED 705
AED 1,682 total
includes taxes & fees
9 Nov - 10 Nov
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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

Cozy Cabin in a rural setting #10 In Temple, NH
Temple
9.0 out of 10, Wonderful, (20 reviews)
"Great place"
United States
Ann S.
The price is AED 436
AED 744 total
includes taxes & fees
6 Nov - 7 Nov
Cozy Cabin in a rural setting #10 In Temple, NH
A modern interior with a dining area, a black chair, and a wall-mounted artwork.

19. Cozy & Stylish 2-bedroom Home in Leominster

Cozy & Stylish 2-bedroom Home in Leominster
Leominster
The price is AED 731
AED 866 total
includes taxes & fees
8 Nov - 9 Nov
Cozy & Stylish 2-bedroom Home in Leominster
Room

20. Cozy Cabin in a Rural setting #8

Cozy Cabin in a Rural setting #8
Temple
8.4 out of 10, Very good, (5 reviews)
"The cabin interiors were something out of a Manhattan boutique hotel. Brand new stylish furnishings"
United States
James M.
The price is AED 393
AED 697 total
includes taxes & fees
6 Nov - 7 Nov
Cozy Cabin in a Rural setting #8
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.
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Top Winchendon Hotel Reviews

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"Nice choice of ordering food you can either eat in the dining area or take back to your room."
Sharon 2-night trip
Posted 2 days ago
Courtyard by Marriott Keene Downtown

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.