Winchendon Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

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$3,090
HK$4,060 total
includes taxes & fees
4 Mar - 5 Mar
Enjoy your stay in an antique home in an antique toy museum!
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, (32 reviews)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is HK$704
HK$1,358 total
includes taxes & fees
15 Mar - 16 Mar
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior

Cozy & Bright Guest Suite

Cozy & Bright Guest Suite
Peterborough
The price is HK$626
HK$1,485 total
includes taxes & fees
8 Mar - 9 Mar
Cozy & Bright Guest Suite
Interior

Cozy Cabin in a Rural setting-14

Cozy Cabin in a Rural setting-14
Temple
9.4 out of 10, Exceptional, (8 reviews)
"Overall a nice stay!"
United States
Jaymes R.
The price is HK$990
HK$1,551 total
includes taxes & fees
4 Mar - 5 Mar
Cozy Cabin in a Rural setting-14
Property grounds

Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (12 reviews)
"BEAUTIFUL surroundings and very peaceful. Would definitely recommend staying here!! "
United States
Vicki L.
The price is HK$1,252
HK$2,249 total
includes taxes & fees
4 Mar - 5 Mar
Cottage beside a waterfall
Exterior

Finnish Cabin with Sauna on Lake Monomonac next to Mt. Monadnock

Finnish Cabin with Sauna on Lake Monomonac next to Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (12 reviews)
"Amazing place. We really enjoyed our brief stay. Great host. "
United States
Gary S.
The price is HK$1,120
HK$2,310 total
includes taxes & fees
9 Mar - 10 Mar
Finnish Cabin with Sauna on Lake Monomonac next to Mt. Monadnock
Smart TV

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 reviews)
"Amazing place very happy will stay again 10 stars "
United States
Dean S.
The price is HK$1,080
HK$1,766 total
includes taxes & fees
4 Mar - 5 Mar
Cozy Cabin in a Rural Setting #16 near Temple,NH
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)
"Nice little cabin, clean other cabins are a little close other than that everything was fine "
United States
Lisa G.
The price is HK$927
HK$1,600 total
includes taxes & fees
15 Mar - 16 Mar
Cozy Cabin in a rural setting (#10) In Temple, NH
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
9.8 out of 10, Exceptional, (25 reviews)
"This is a great property, and Jim is a wonderful host. He accommodated all our requests for sauna use and provided helpful tips about the area. We hope to return again one day!"
United States
Leigh C.
The price is HK$1,557
HK$3,098 total
includes taxes & fees
9 Mar - 10 Mar
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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, (30 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is HK$1,174
HK$3,390 total
includes taxes & fees
15 Mar - 16 Mar
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Outdoor spa tub

Modern Downtown 12ppl Hot Tub Fire Pit Games

Modern Downtown 12ppl Hot Tub Fire Pit Games
Keene
9.6 out of 10, Exceptional, (22 reviews)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is HK$1,097
HK$2,302 total
includes taxes & fees
9 Mar - 10 Mar
Modern Downtown 12ppl Hot Tub Fire Pit Games
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)
"Great location host was on it.anything u needed he was there.no ac was the only thing.but it was unusally hot.i would go again"
United States
Brian
The price is HK$1,400
HK$2,903 total
includes taxes & fees
9 Mar - 10 Mar
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Property grounds

River Room overlooking the waterfall

River Room overlooking the waterfall
Wilton
10.0 out of 10, Exceptional, (3 reviews)
"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$1,252
HK$2,249 total
includes taxes & fees
4 Mar - 5 Mar
River Room overlooking the waterfall
Interior

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
Greenfield
10.0 out of 10, Exceptional, (13 reviews)
"Its was great clean, quite and comfortable. "
United States
John G.
The price is HK$1,303
HK$1,897 total
includes taxes & fees
4 Mar - 5 Mar
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
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, (25 reviews)
"Our family stayed at the house for 2 nights to attend a nearby wedding. The house was just as pictured - lovely, clean, and perfect for our stay. The hosts have been very thoughtful about every detail from easy check-in to a well stocked kitchen to cozy blankets for the comfy couch. We had a wonderful time and highly recommend! "
United States
Kelly G.
The price is HK$1,956
HK$4,257 total
includes taxes & fees
22 Mar - 23 Mar
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Exterior

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
Wilton
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful and thoughtful hosts that went above and beyond to make us feel at home. We appreciated the coziness of the house and your kindness. "
United States
Kadie H.
The price is HK$1,267
HK$2,750 total
includes taxes & fees
8 Mar - 9 Mar
Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School
Smart TV, fireplace, printers

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, (23 reviews)
"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$1,197
HK$2,555 total
includes taxes & fees
10 Mar - 11 Mar
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Private kitchen

Large 3BR Apartment in Marlborough NH: Sleeps 8-10: Close to Keene!

Large 3BR Apartment in Marlborough NH: Sleeps 8-10: Close to Keene!
Marlborough
10.0 out of 10, Exceptional, (2 reviews)
"Clean and close to Keene! Very quiet and had a great nights rest!"
United States
Sierra M.
The price is HK$1,095
HK$2,810 total
includes taxes & fees
4 Mar - 5 Mar
Large 3BR Apartment in Marlborough NH: Sleeps 8-10: Close to Keene!
Exterior

Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
10.0 out of 10, Exceptional, (1 review)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
Central Large 2-bedrooms with office in Keene
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

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

10/10 Excellent
"Everything was clean and the staff was friendly. "
Kimberly 1-night trip
Posted 5 days ago
Fairfield Inn & Suites by Marriott Keene Downtown

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:

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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 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?

Spacious lakeside 4-bedroom house in beautiful Ashburnham: This highly rated holiday home rental in Winchendon is equipped with a fireplace, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop and a microwave. Another good choice for your trip to Winchendon is Cozy Lakefront Cottage.

How many holiday rentals will I find in Winchendon?

Choose from 8 Expedia holiday rentals in Winchendon for a memorable holiday.

What’s there to see and do in Winchendon?

Wendall P. Clark Memorial and Blueberry Island 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 Otter River State Forest 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.