Winchendon Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Winchendon vacation 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 ￥51,734
￥62,256 total
includes taxes & fees
May 25 - May 26
Enjoy your stay in an antique home in an antique toy museum!
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 ￥8,755
￥12,954 total
includes taxes & fees
May 25 - May 26
2 private mountain RV pads for rent. Full hook ups
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, (35 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 ￥13,610
￥26,857 total
includes taxes & fees
May 25 - May 26
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
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 ￥17,573
￥31,156 total
includes taxes & fees
May 27 - May 28
Cozy Cabin in a rural setting #10 In Temple, NH
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, (20 reviews)
"Amazing place very happy will stay again 10 stars "
United States
Dean S.
The price is ￥21,967
￥36,269 total
includes taxes & fees
May 26 - May 27
Cozy Cabin in a Rural Setting #16 near Temple,NH
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 ￥20,136
￥31,723 total
includes taxes & fees
May 26 - May 27
Cozy Cabin in a Rural setting-14
Property grounds

Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (13 reviews)
"BEAUTIFUL surroundings and very peaceful. Would definitely recommend staying here!! "
United States
Vicki L.
The price is ￥25,469
￥44,042 total
includes taxes & fees
May 25 - May 26
Cottage beside a waterfall
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
9.8 out of 10, Exceptional, (26 reviews)
"Host was incredibly friendly and accommodating and the cabin was nothing short of beautiful"
United States
Moose C.
The price is ￥37,750
￥57,885 total
includes taxes & fees
May 27 - May 28
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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, (15 reviews)
"Charming location and beautiful setting. "
United States
Cherie G.
The price is ￥29,448
￥41,452 total
includes taxes & fees
May 26 - May 27
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
Exterior

2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is ￥85,814
￥124,369 total
includes taxes & fees
Jun 1 - Jun 2
2 Cabins & Sauna on Lake Monomonac
Exterior

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

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Westminster
10.0 out of 10, Exceptional, (37 reviews)
"We had a wonderful stay at this lake-front cottage looking up at the nearby ski resort. The cottage was cozy and quiet in a great location. The check-in process was easy, and the owner was very accessible. Terrific rental!"
United States
Lane D.
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Property grounds

John's Mountain Hideaway

John's Mountain Hideaway
Jaffrey
The price is ￥39,795
￥78,584 total
includes taxes & fees
May 29 - May 30
John's Mountain Hideaway
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, (35 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is ￥31,836
￥79,802 total
includes taxes & fees
May 28 - May 29
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
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 ￥27,888
￥43,386 total
includes taxes & fees
May 26 - May 27
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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, (25 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is ￥27,061
￥53,023 total
includes taxes & fees
May 27 - May 28
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Property grounds

River Room overlooking the waterfall

River Room overlooking the waterfall
Wilton
10.0 out of 10, Exceptional, (5 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 ￥25,469
￥45,424 total
includes taxes & fees
May 25 - May 26
River Room overlooking the waterfall
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 ￥60,106
￥100,936 total
includes taxes & fees
Jun 14 - Jun 15
Feels Like Home - BBQ, Yard, Fire Pit
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, (28 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
1 bedroom, desk, iron/ironing board, WiFi

Cozy Cabin in a Rural setting #8

Cozy Cabin in a Rural setting #8
Temple
9.0 out of 10, Wonderful, (4 reviews)
"Cute, cozy and clean. "
United States
Jessica F.
The price is ￥21,235
￥32,994 total
includes taxes & fees
May 25 - May 26
Cozy Cabin in a Rural setting #8
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 ￥30,093
￥48,712 total
includes taxes & fees
Jun 21 - Jun 22
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

10/10 Excellent
"The hotel bar, called "Nectar", Is an unpretentious and comfortable place to have a conversation and a drink in the evening. Its kitchen has a limited menu of well prepared entrees, sandwiches, and salads."
Jim 4-night trip
Posted 9 hours ago
Doubletree by Hilton Hotel Leominster

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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Frequently asked questions

Are there vacation rentals in Winchendon?

Yes, we offer vacation rentals in Winchendon near The Robinson-Broadhurst Foundation Performing Arts Ampitheater, or you can choose a secluded option if you're looking for extra privacy while you relax. Winchendon is known for its parks.

What are some of the best vacation rentals that Winchendon has to offer?

Cozy Lakefront Cottage: Visitors give good reviews to this Winchendon vacation home rental, which is located on a lake and has a patio, a garden, and a barbecue grill 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 vacation with amenities like a selection of books.

How many vacation rentals will I find in Winchendon?

Choose from 7 Expedia vacation rentals in Winchendon for a memorable vacation.

What’s there to see and do in Winchendon?

V F W Park and Blueberry Island are a couple of lovely local spots to get outside and enjoy nature. Lake Dennison State Recreation Area and Beals Memorial Library are other places to visit while you're in town.

What’s a vacation rental in Winchendon like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Winchendon. Vacation rentals offer extras such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.