Winchendon Holiday Rentals

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Holiday Rentals in Winchendon

Interior
Enjoy your stay in an antique home in an antique toy museum!
9.2 out of 10, Wonderful, (7)
"A unique enjoyable experience "
The price is HK$3,084
per night
17 May - 18 May
Enjoy your stay in an antique home in an antique toy museum!
Interior
Charming Waterfront Log Cabin
10.0 out of 10, Exceptional, (24)
"Wonderful place it’s are 3rd time staying there an you can’t beat the location, pond view or the nature surrounding you. An a very fast response. I will be staying agsin!"
The price is HK$1,367
per night
11 Jun - 12 Jun
Charming Waterfront Log Cabin
Smart TV
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
10.0 out of 10, Exceptional, (7)
"Everything was perfect and two minutes to Wachusett ski mountain."
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
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Exterior
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, (34)
"Linda was wonderful in her review of the property and was very accommodating in all aspects of our stay. The cottage was well equipped and very comfortable including the mattress. We enjoyed the lake and a little fishing. The area is very nice and we did some exploring. It was very quiet and we rarely even saw anyone while we were on the lake. We hope to return in the spring or summer. Many thanks to Linda and Brad"
Waterfront Cottage on Scenic Sportsman Pond
Exterior
Sweet Retreat and Yurt Farm
10.0 out of 10, Exceptional, (2)
"We had a really nice time in the yurt– it's beautifully decorated on the inside, very cozy and the hosts were super nice and welcoming. Would definitely recommend staying here!"
The price is HK$742
per night
9 Jun - 10 Jun
Sweet Retreat and Yurt Farm
Fridge, microwave, oven, stovetop
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
10.0 out of 10, Exceptional, (2)
"Very clean and centrally located in Peterborough. Check in was flexible and easy. Hosts were very friendly."
The price is HK$703
per night
19 May - 20 May
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!
9.8 out of 10, Exceptional, (78)
"We had a great get-away down to Wachusett Mountain with our two famlies, lots of room for everyone and very comfortable and close to the ski area and restaurants/groceries. Thank you!"
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!
Interior
Relaxing Retreat
10.0 out of 10, Exceptional, (16)
"Great location for our stay. Clean and comfortable"
Relaxing Retreat
Property grounds
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, (6)
"Crystal was an exceptional hostess! "
Lakefront Orange Vacation Rental - Pet Friendly!
Property grounds
Quiet private pond getaway
9.6 out of 10, Exceptional, (4)
"Needed a long weekend getaway. Perfect spot located in nature, great fishing and fall foliage."
Quiet private pond getaway
Fridge, microwave, stovetop, coffee/tea maker
Cozy Cabin in a Rural Setting #16 near Temple,NH
10.0 out of 10, Exceptional, (4)
"It’s a cute little cabin with modern amenities. No supplies like tea coffee in the room but it did not matter to us :)"
The price is HK$1,015
per night
22 May - 23 May
Cozy Cabin in a Rural Setting #16 near Temple,NH
Property grounds
Downtown Hot Tub Escape
9.4 out of 10, Exceptional, (3)
"Wonderfully located not to far from plenty of great restaurants and really well kept home that accomadated 9 adults for the night perfectly. Clear instructions for all the amenities in the home made it easy and fun."
The price is HK$1,406
per night
19 May - 20 May
Downtown Hot Tub Escape
Property grounds
Lovely 3-bedroom City Escape
9.8 out of 10, Exceptional, (14)
"Everything was fine"
Lovely 3-bedroom City Escape
Exterior
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
10.0 out of 10, Exceptional, (53)
"We were looking for a somewhat rural place for lots of family members could have their own quarters. This place fulfilled it all. Close to everything and yet it felt remote. Easy place to relax. Just what we wanted."
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Aerial view
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
9.8 out of 10, Exceptional, (8)
"We were looking for somewhere to stay that was close to Mount Wachusett. The cottage was very clean, cozy, and had many amenities including a fully stocked kitchen and an electric fireplace . Though we were for skiing there during the wintertime, the cottage is on a lake and kayaking is also an option during the summer. The hosts were quickly available to us with any questions. There is even a complimentary bottle of wine to enjoy!"
The price is HK$1,562
per night
12 Jun - 13 Jun
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Property grounds
Charming Cottage by the Lake
Charming Cottage by the Lake
Lake
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, (8)
"The house was superb for our family visit! We enjoyed it all! Linda was a perfect hostess…,so attentive!"
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
4 bedrooms, desk, iron/ironing board, Internet
Historic Home w/ Modern Updates on 3.5 Acres
10.0 out of 10, Exceptional, (5)
"The property was awesome! Old, quaint and brought memories back of our grandparents homes…Family sat around table and enjoyed shared memories"
Historic Home w/ Modern Updates on 3.5 Acres
Fridge, microwave, stovetop, dishwasher
Cozy Getaway - 10 Miles to Mount Wachusett Skiing!
10.0 out of 10, Exceptional, (8)
"This place was cozy and perfect. My daughter recently moved to the area and so I wanted to find a place that I hoped will become a home away from home for my husband and I whenever we visit, and we found it! The bed was comfortable. It's a king size bed, and they are sometimes hard to find so we were thrilled by that. The kitchen has all of your needs, we cooked a few meals and had all the pots and pans we needed. The couch and big chair were also comfy for our movie nights, when our daughter...
Cozy Getaway - 10 Miles to Mount Wachusett Skiing!
Property grounds
Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks
10.0 out of 10, Exceptional, (7)
"Beautiful property with multiple seating areas and views of the lake. Joe is very easy to work with and the boat tour was terrific."
Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks
Don't see what you're looking for?
See all available properties in Winchendon
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.

Other types of properties in Winchendon you may be interested in

Interior
Enjoy your stay in an antique home in an antique toy museum!
9.2 out of 10, Wonderful, (7)
"A unique enjoyable experience "
The price is HK$3,084
per night
17 May - 18 May
Enjoy your stay in an antique home in an antique toy museum!
4 indoor pools, seasonal outdoor pool, pool cabanas (surcharge)
Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
8.6 out of 10, Excellent, (686)
The price is HK$1,398
per night
22 May - 23 May
Great Wolf Lodge Boston / Fitchburg, MA
Lobby
Motel 6 Leominster, MA
2.0 star property
7.4 out of 10, Good, (1001)
"This is definitely a no-frills, basic place to stay. But, it’s convenient to the highway, restaurants, allows dogs, and is affordable. It seems to house many who are transitioning from homelessness to apartments. Everyone I’ve encountered has been friendly & loved my dog. Usually very quiet after 9pm, but I did have 1 night of no sleep due to a party/LOUD truck running through the parking lot all hours. "
The price is HK$759
per night
16 Jun - 17 Jun
Motel 6 Leominster, MA
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.

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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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.

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?

Lake Dennison State Recreation Area and Millers River are a couple of lovely local spots to get outside and enjoy nature. The Winchendon School and Wetmore Trailhead are a couple of places you'll find in the wider area.

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.

Recent reviews of Winchendon properties
Expedia verified reviews

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

5/5 Excellent
"Room was available prior to 4pm and staff was very nice and followed up each day to understand how our stay was going."
A verified traveller stayed at Doubletree by Hilton Hotel Leominster
Posted 3 days ago
Doubletree by Hilton Hotel Leominster