A hilly landscape with a tower on top, dense forest, and a cloudy sky.

Winchendon Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

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 AED 1,194
AED 1,425 total
includes taxes & fees
12 Jul - 13 Jul
Enjoy your stay in an antique home in an antique toy museum!
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, (38 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is AED 1,102
AED 2,273 total
includes taxes & fees
26 Jul - 27 Jul
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
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, (33 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is AED 973
AED 2,063 total
includes taxes & fees
5 Aug - 6 Aug
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
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)
The price is AED 1,837
AED 3,179 total
includes taxes & fees
17 Jul - 18 Jul
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Property grounds

Cottage beside a waterfall

Cottage beside a waterfall
Wilton
9.8 out of 10, Exceptional, (17 reviews)
"BEAUTIFUL surroundings and very peaceful. Would definitely recommend staying here!! "
United States
Vicki L.
The price is AED 588
AED 1,056 total
includes taxes & fees
19 Jul - 20 Jul
Cottage beside a waterfall
Property grounds

River Room overlooking the waterfall

River Room overlooking the waterfall
Wilton
10.0 out of 10, Exceptional, (6 reviews)
"Incredible property!! Hands down best stay during our trip."
United States
Makayla M.
The price is AED 588
AED 1,056 total
includes taxes & fees
12 Jul - 13 Jul
River Room overlooking the waterfall
Exterior detail

Cozy Cabin in a rural setting #12 in Temple NH

Cozy Cabin in a rural setting #12 in Temple NH
Temple
9.4 out of 10, Exceptional, (16 reviews)
"Amazing best place in nh"
United States
Dean S.
The price is AED 296
AED 600 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Cabin in a rural setting #12 in Temple NH
Interior

Cozy Cabin in a Rural setting-14

Cozy Cabin in a Rural setting-14
Temple
9.2 out of 10, Wonderful, (10 reviews)
"Place was a very nice stay, area was close to nice places."
United States
Rui V.
The price is AED 338
AED 601 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Cabin in a Rural setting-14
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, (22 reviews)
"Amazing place very happy will stay again 10 stars "
United States
Dean S.
The price is AED 380
AED 691 total
includes taxes & fees
12 Jul - 13 Jul
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)
"Great place"
United States
Ann S.
The price is AED 296
AED 600 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Cabin in a rural setting #10 In Temple, NH
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 AED 296
AED 559 total
includes taxes & fees
12 Jul - 13 Jul
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
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 AED 1,327
AED 1,862 total
includes taxes & fees
13 Jul - 14 Jul
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
8.0 out of 10, Very Good, (5 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 AED 1,249
AED 1,813 total
includes taxes & fees
14 Jul - 15 Jul
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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, (39 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is AED 397
AED 713 total
includes taxes & fees
13 Jul - 14 Jul
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Fridge, microwave, oven, stovetop

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, (26 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is AED 1,543
AED 2,654 total
includes taxes & fees
12 Jul - 13 Jul
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Property grounds

John's Mountain Hideaway

John's Mountain Hideaway
Jaffrey
10.0 out of 10, Exceptional, (1 review)
"Everything we needed"
United States
Lori S.
The price is AED 1,021
AED 1,941 total
includes taxes & fees
13 Jul - 14 Jul
John's Mountain Hideaway
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (25 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is AED 718
AED 1,329 total
includes taxes & fees
13 Jul - 14 Jul
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Fridge, microwave, oven, stovetop

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (3 reviews)
The price is AED 786
AED 1,861 total
includes taxes & fees
15 Jul - 16 Jul
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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 AED 202
AED 299 total
includes taxes & fees
11 Jul - 12 Jul
2 private mountain RV pads for rent. Full hook ups
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchendon Hotel Reviews

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

8/10 Good
"The room was comfortable and for the most part clean. Only things that could have been better were the bathroom sink wasn’t clean and the drinking glasses were hazy and had smudges."
Patrick 4-night trip
Posted 1 hour ago
Courtyard by Marriott Keene Downtown

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?

Blueberry Island and Millers River 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.