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

Winchendon Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Winchendon holiday rentals

Interior

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, (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
Katja Z.
The price is HK$2,547
HK$3,073 total
includes taxes & fees
21 Jun - 22 Jun
Enjoy your stay in an antique home in an antique toy museum!
Smart TV

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

Cozy Cabin in a Rural Setting #16 near Temple,NH
Temple
9.6 out of 10, Exceptional, (21 reviews)
"Amazing place very happy will stay again 10 stars "
United States
Dean S.
The price is HK$1,082
HK$1,794 total
includes taxes & fees
21 Jun - 22 Jun
Cozy Cabin in a Rural Setting #16 near Temple,NH
Exterior detail

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, (37 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is HK$811
HK$1,475 total
includes taxes & fees
22 Jun - 23 Jun
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Property grounds

Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (15 reviews)
"BEAUTIFUL surroundings and very peaceful. Would definitely recommend staying here!! "
United States
Vicki L.
The price is HK$1,254
HK$2,194 total
includes taxes & fees
30 Jun - 1 Jul
Cottage beside a waterfall
Interior

Cozy Cabin in a Rural setting-14

Cozy Cabin in a Rural setting-14
Temple
9.4 out of 10, Exceptional, (8 reviews)
"Place was a very nice stay, area was close to nice places."
United States
Rui V.
The price is HK$991
HK$1,562 total
includes taxes & fees
21 Jun - 22 Jun
Cozy Cabin in a Rural setting-14
Property grounds

River Room overlooking the waterfall

River Room overlooking the waterfall
Wilton
10.0 out of 10, Exceptional, (6 reviews)
"Incredible property!! Hands down best stay during our trip."
United States
Makayla M.
The price is HK$1,254
HK$2,270 total
includes taxes & fees
26 Jun - 27 Jun
River Room overlooking the waterfall
Exterior

Modern 3BR Near FSU • 15 Min to Wachusett

Modern 3BR Near FSU • 15 Min to Wachusett
Fitchburg
10.0 out of 10, Exceptional, (15 reviews)
"House was amazing, great people to work with! "
United States
Keith
Modern 3BR Near FSU • 15 Min to Wachusett
Smart TV

Mid-Century Comfort & Style

Mid-Century Comfort & Style
Fitchburg
9.6 out of 10, Exceptional, (12 reviews)
"What a great place! Very clean, and comfortable. Several very good local restaurants within walking distance. Can’t say enough good things to say. Next time we are in the area, this will be our first pick for a place to stay."
United States
Robert
The price is HK$1,495
HK$3,216 total
includes taxes & fees
23 Jun - 24 Jun
Mid-Century Comfort & Style
1 bedroom, desk, iron/ironing board, WiFi

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, (19 reviews)
"Great place"
United States
Ann S.
The price is HK$865
HK$1,543 total
includes taxes & fees
9 Jul - 10 Jul
Cozy Cabin in a rural setting #10 In Temple, NH
Exterior

2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is HK$8,457
HK$11,446 total
includes taxes & fees
30 Jun - 1 Jul
2 Cabins & Sauna on Lake Monomonac
Property grounds

John's Mountain Hideaway

John's Mountain Hideaway
Jaffrey
10.0 out of 10, Exceptional, (1 review)
"Everything we needed"
United States
Lori S.
The price is HK$2,320
HK$4,277 total
includes taxes & fees
8 Jul - 9 Jul
John's Mountain Hideaway
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.2 out of 10, Wonderful, (26 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is HK$1,532
HK$2,819 total
includes taxes & fees
22 Jun - 23 Jun
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
7.6 out of 10, Good, (4 reviews)
"Hit the jackpot at this stay .Awesome area with many things to keep busy outside ,hiking all around ,lake for all kind of activities .Jim was a great host filled us in on activities in the area and was a message away for any help u may need .I will be back ."
United States
David S.
The price is HK$2,998
HK$4,264 total
includes taxes & fees
28 Jun - 29 Jun
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (12 reviews)
"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "
United States
Rebecca
The price is HK$2,998
HK$4,137 total
includes taxes & fees
26 Jun - 27 Jun
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Smart TV

Feels Like Home - BBQ, Yard, Fire Pit

Feels Like Home - BBQ, Yard, Fire Pit
Fitchburg
9.4 out of 10, Exceptional, (3 reviews)
"The pictures of the property do not do it justice. The home is so beautiful and comfortable. Check-in was simple. Definitely recommend this rental!"
United States
Amy F.
The price is HK$1,154
HK$2,749 total
includes taxes & fees
19 Jul - 20 Jul
Feels Like Home - BBQ, Yard, Fire Pit
Fridge, microwave, oven, stovetop

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

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (3 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 HK$1,505
HK$3,758 total
includes taxes & fees
22 Jun - 23 Jun
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Exterior

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Westminster
9.6 out of 10, Exceptional, (37 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is HK$2,351
HK$4,849 total
includes taxes & fees
6 Jul - 7 Jul
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Outdoor dining

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is HK$431
HK$638 total
includes taxes & fees
20 Jun - 21 Jun
2 private mountain RV pads for rent. Full hook ups
Smart TV

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, (30 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is HK$2,081
HK$4,415 total
includes taxes & fees
1 Jul - 2 Jul
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Exterior detail

Cozy Cabin in a rural setting #12 in Temple NH

Cozy Cabin in a rural setting #12 in Temple NH
Temple
9.4 out of 10, Exceptional, (16 reviews)
"Amazing best place in nh"
United States
Dean S.
The price is HK$784
HK$1,446 total
includes taxes & fees
21 Jun - 22 Jun
Cozy Cabin in a rural setting #12 in Temple NH
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

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent
"Todo limpio y organizado y las atenciones muy buenas."
Milagros 1-night trip
Posted 3 hours ago
Great Wolf Lodge Boston / Fitchburg, MA

Find out more about Winchendon

Search for holiday rentals in Winchendon on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchendon using one of the methods below:

  • View our selection of featured holiday rentals in Winchendon
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Look no further and take a look at our great range of rental properties in Winchendon!

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 7 Expedia holiday rentals in Winchendon for a memorable holiday.

What’s there to see and do in Winchendon?

Militia Training Field and Old Centre Historic District are a couple of lovely local spots to get outside and enjoy nature. Lake Dennison State Recreation Area and Blueberry Island 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.