Winchendon Holiday Rentals

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Holiday Rentals in Winchendon

Cozy Lakefront Cottage
Exterior

Cozy Lakefront Cottage

9.8 out of 10, Exceptional, (16)
"Me and my children had an amazing time exploring the lake."
Cozy Lakefront Cottage
Modern Waterfront Gem w/ Dock on Lake Monomonac
Interior

Modern Waterfront Gem w/ Dock on Lake Monomonac

3.0 star property
Modern Waterfront Gem w/ Dock on Lake Monomonac
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Outdoor dining

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

10.0 out of 10, Exceptional, (4)
"This comfortable 2-bedroom house on a tranquil NH pond was the perfect weekend escape! We absolutely loved the peaceful setting and beautiful views. It was incredibly relaxing and exactly what we needed. Highly recommend!"
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Exterior

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.4 out of 10, Exceptional, (26)
"a fantastic weekend getaway in the mountains! quiet neighborhood with stunning night time views of the stars. such a cozy cabin, very clean, linens provided, nice property with a little fire pit too! very friendly host, easy to contact and pleasant. "
The price is HK$919
HK$2,055 total
includes taxes & fees
1 Sept - 2 Sept
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Cozy Cabin in a Rural setting-14
1 bedroom, free WiFi, bed sheets

Cozy Cabin in a Rural setting-14

8.8 out of 10, Excellent, (5)
"It was a cute nice space. Close to outlets and plenty of trails for hiking. The cabin was also just a nice space to relax."
The price is HK$1,076
HK$1,867 total
includes taxes & fees
1 Sept - 2 Sept
Cozy Cabin in a Rural setting-14
Modern Mid-Century in Fitchburg
Fridge, microwave, oven, stovetop

Modern Mid-Century in Fitchburg

9.8 out of 10, Exceptional, (6)
"Great property close to where we needed to be."
Modern Mid-Century in Fitchburg
Downtown Hot Tub Escape
Fridge, microwave, oven, stovetop

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (17)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is HK$1,855
HK$3,222 total
includes taxes & fees
2 Sept - 3 Sept
Downtown Hot Tub Escape
Quiet private pond getaway
Property grounds

Quiet private pond getaway

9.4 out of 10, Exceptional, (14)
"We really enjoyed our time at the lake house! The deck and fire pit was fun and everything was very nicely decorated and had enough supplies to make it very easy and a quiet peaceful setting!"
Quiet private pond getaway
Cozy Cabin in a Rural setting #8
Exterior detail

Cozy Cabin in a Rural setting #8

6.0 out of 10, (1)
"The cabin itself was okay. Could have been cleaner and if we had stayed more than one night I would have said something. Mold in shower, crumbs under microwave, dusty windowsills. No top sheet on bed. The area surrounding was just dirt and gravel and a couple of ugly outbuildings with junk all around. The cabins themselves looked fine but otherwise was not pretty"
The price is HK$915
HK$1,491 total
includes taxes & fees
31 Aug - 1 Sept
Cozy Cabin in a Rural setting #8
2 queen and 2 twin beds
Interior

2 queen and 2 twin beds

9.6 out of 10, Exceptional, (10)
"We really enjoyed our stay. The seating outside was lovely!"
2 queen and 2 twin beds
Charming Waterfront Log Cabin
3 bedrooms, travel cot, free WiFi, bed sheets

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (41)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
Lemon Drop Cottage a private cottage getaway
Property grounds

Lemon Drop Cottage a private cottage getaway

9.4 out of 10, Exceptional, (46)
"Straightforward check-in, very nice host. Great short stay."
The price is HK$1,637
HK$1,971 total
includes taxes & fees
7 Sept - 8 Sept
Lemon Drop Cottage a private cottage getaway
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Exterior

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

10.0 out of 10, Exceptional, (13)
"Loved the area"
The price is HK$1,060
HK$1,726 total
includes taxes & fees
9 Sept - 10 Sept
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
New and Modern 3 B- 5 min FSU - 15 min Wachusett's
Fridge, microwave, oven, stovetop

New and Modern 3 B- 5 min FSU - 15 min Wachusett's

10.0 out of 10, Exceptional, (3)
"Wonderful place to stay. Everything was very clean, comfortable, and spacious, with a warm, welcoming feel. I highly recommend the place to stay. "
New and Modern 3 B- 5 min FSU - 15 min Wachusett's
Cottage beside a waterfall
Property grounds

Cottage beside a waterfall

9.4 out of 10, Exceptional, (3)
"What a unique place to stay with a waterfall in the backyard! Quiet, beautiful grounds on the property. Clean, private and well appointed. "
The price is HK$1,130
HK$2,021 total
includes taxes & fees
2 Sept - 3 Sept
Cottage beside a waterfall
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Smart TV

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

10.0 out of 10, Exceptional, (21)
"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. "
The price is HK$1,754
HK$4,002 total
includes taxes & fees
7 Sept - 8 Sept
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Exterior

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

9.8 out of 10, Exceptional, (20)
"Beautiful place"
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
River Room overlooking the waterfall
Outdoor dining

River Room overlooking the waterfall

10.0 out of 10, Exceptional, (1)
"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."
The price is HK$1,130
HK$2,021 total
includes taxes & fees
2 Sept - 3 Sept
River Room overlooking the waterfall
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (22)
"great location"
The price is HK$807
HK$1,467 total
includes taxes & fees
3 Sept - 4 Sept
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!
Exterior

Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!

9.8 out of 10, Exceptional, (51)
"Ryan’s property is beautiful and peaceful. Its exactly what I would describe as a perfect summer getaway."
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!
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

Find out more about Winchendon

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
  • Use the map to find apartments and other holiday homes in the Winchendon neighbourhood you prefer
  • 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?

Modern Waterfront Gem w/ Dock on Lake Monomonac: This highly rated holiday home rental in Winchendon is located on a lake, and has a selection of games, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, kitchenware and a coffee maker.

How many holiday rentals will I find in Winchendon?

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

What’s there to see and do in Winchendon?

Millers River and V F W Park 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 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.