Winchendon Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Winchendon

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, (29)
"Nice location and a very cool place to stay "
United States
Samson M.
The price is HK$779
HK$2,912 total
includes taxes & fees
9 Dec - 10 Dec
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Exterior detail
Cozy Cabin in a Rural setting #8

Cozy Cabin in a Rural setting #8

Temple
9.0 out of 10, Wonderful, (4)
"Cute, cozy and clean. "
United States
Jessica F.
The price is HK$914
HK$1,489 total
includes taxes & fees
5 Dec - 6 Dec
Cozy Cabin in a Rural setting #8
Fridge, microwave, oven, stovetop
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, (29)
"I had a great stay at Mary Anne and Ben’s place in Peterborough. The apartment was clean and comfortable, and the location cannot be beat."
United States
Joseph K.
The price is HK$490
HK$1,123 total
includes taxes & fees
3 Dec - 4 Dec
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Fitzwilliam
10.0 out of 10, Exceptional, (13)
"Loved the area"
United States
Jose R.
The price is HK$974
HK$1,623 total
includes taxes & fees
3 Dec - 4 Dec
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Exterior
Tiny house on the Ashuelot river family and pet friendly

Tiny house on the Ashuelot river family and pet friendly

Swanzey
The price is HK$467
HK$676 total
includes taxes & fees
9 Dec - 10 Dec
Tiny house on the Ashuelot river family and pet friendly
1 bedroom, free WiFi, bed sheets
Cozy Cabin in a Rural setting-14

Cozy Cabin in a Rural setting-14

Temple
9.4 out of 10, Exceptional, (8)
"A wonderful little cabin. Everything was as cute and clean as the pictures and descriptions. You will love this place!"
United States
Craig
The price is HK$1,074
HK$1,847 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Cabin in a Rural setting-14
Exterior
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)
"Nice little cabin, clean other cabins are a little close other than that everything was fine "
United States
Lisa G.
The price is HK$914
HK$1,786 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Cabin in a rural setting (#10) In Temple, NH
Property grounds
Cottage beside a waterfall

Cottage beside a waterfall

Wilton
9.8 out of 10, Exceptional, (10)
"What a unique place to stay with a waterfall in the backyard! Quiet, beautiful grounds on the property. Clean, private and well appointed. "
United States
Marcella J.
The price is HK$1,246
HK$2,179 total
includes taxes & fees
3 Dec - 4 Dec
Cottage beside a waterfall
Terrace/patio
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Rindge
10.0 out of 10, Exceptional, (22)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
United States
Nicole B.
The price is HK$1,366
HK$2,893 total
includes taxes & fees
3 Dec - 4 Dec
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Fridge, microwave, oven, stovetop
Downtown Hot Tub Escape

Downtown Hot Tub Escape

Keene
9.6 out of 10, Exceptional, (21)
"Nice house in a nice location. "
United States
Rob B.
The price is HK$986
HK$2,176 total
includes taxes & fees
3 Dec - 4 Dec
Downtown Hot Tub Escape
Fridge, microwave, oven, stovetop
Modern 3BR Near FSU • 15 Min to Wachusett

Modern 3BR Near FSU • 15 Min to Wachusett

Fitchburg
10.0 out of 10, Exceptional, (12)
"Wonderful place to stay. Everything was very clean, comfortable, and spacious, with a warm, welcoming feel. I highly recommend the place to stay. "
United States
Catherine
The price is HK$1,036
HK$2,431 total
includes taxes & fees
11 Dec - 12 Dec
Modern 3BR Near FSU • 15 Min to Wachusett
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, (23)
"Kathleen was an amazing host and the property exceeded our expectations. The kids loved the bunk room and loft and the surrounding area provided something for all interests. We will definitely be planning another stay. "
United States
Michael T.
The price is HK$1,752
HK$4,023 total
includes taxes & fees
9 Dec - 10 Dec
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Interior
Charming cabin in delightful Greenfield New Hampshire with WiFi access

Charming cabin in delightful Greenfield New Hampshire with WiFi access

Greenfield
9.8 out of 10, Exceptional, (8)
"Its was great clean, quite and comfortable. "
United States
John G.
The price is HK$1,440
HK$2,053 total
includes taxes & fees
3 Dec - 4 Dec
Charming cabin in delightful Greenfield New Hampshire with WiFi access
Outdoor dining
River Room overlooking the waterfall

River Room overlooking the waterfall

Wilton
10.0 out of 10, Exceptional, (3)
"Had a great time, the grounds are spectacular with the river waterfall in the background. The Bathroom was stunning. Had everything we needed. The bed was super comfy too. The screened-in porch was convenient, too."
United States
Romie G.
The price is HK$1,246
HK$2,238 total
includes taxes & fees
3 Dec - 4 Dec
River Room overlooking the waterfall
Property grounds
Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School

Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School

2.0 star property
Wilton
10.0 out of 10, Exceptional, (1)
"Christine was so personally welcoming. Was flying into Boston on the red eye and needed to check in early and she not only accommodated that request, she left us pancake mix, local maple syrup, butter and a fresh carton of half and half for coffee for our early morning. The amenities were all top notch. I’m a big fan of doterra essentials so it was nice to see them being used. "
United States
Joseph C.
The price is HK$1,401
HK$2,906 total
includes taxes & fees
7 Dec - 8 Dec
Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School
Fridge, microwave, stovetop, coffee/tea maker
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, (17)
"Super cute cabin with updated features and it was cozy and recently updated. The bed was particularly comfortable and the efficient layout made it possible for four adults to stay. Parking was easy and checkin and communication with the host was excellent before and after our stay. Would highly reccommend!"
United States
Kevin H.
The price is HK$1,182
HK$1,924 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Cabin in a Rural Setting #16 near Temple,NH
Interior
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Dublin
10.0 out of 10, Exceptional, (25)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is HK$2,345
HK$4,469 total
includes taxes & fees
7 Dec - 8 Dec
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Interior
Entire private apartment suite in home with own entrance, views and private gym.

Entire private apartment suite in home with own entrance, views and private gym.

Keene
The price is HK$1,927
HK$2,834 total
includes taxes & fees
15 Dec - 16 Dec
Entire private apartment suite in home with own entrance, views and private gym.
Outdoor dining
Charming Home Walk to Downtown!

Charming Home Walk to Downtown!

Keene
10.0 out of 10, Exceptional, (2)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
The price is HK$1,907
HK$5,034 total
includes taxes & fees
4 Dec - 5 Dec
Charming Home Walk to Downtown!
Terrace/patio
Unique Cozy private 1-bedroom apartment in charming Temple

Unique Cozy private 1-bedroom apartment in charming Temple

Temple
9.8 out of 10, Exceptional, (7)
"very clean, well decorated, comfortable and peaceful"
United States
Dan G.
The price is HK$2,725
HK$3,379 total
includes taxes & fees
7 Dec - 8 Dec
Unique Cozy private 1-bedroom apartment in charming Temple
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
"We had a great time.. lots to do."
Donatella 2-night trip
Posted 2 days 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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  • Enter your travel dates to view the best deals on holiday rentals in Winchendon while they last

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 close to the most popular sights in Winchendon, 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 5 Expedia holiday rentals in Winchendon for a memorable holiday.

What’s there to see and do in Winchendon?

Wendall P. Clark Memorial and Militia Training Field are a couple of scenic spots to enjoy the outdoors, whereas The Robinson-Broadhurst Foundation Performing Arts Ampitheater is one of the cultural attractions. Lake Dennison State Recreation Area and Winchendon Town Hall 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.