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
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

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 ￥63,014
￥82,794 total
includes taxes & fees
Apr 5 - Apr 6
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 ￥7,019
￥11,077 total
includes taxes & fees
May 1 - May 2
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, (33 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 ￥12,933
￥26,160 total
includes taxes & fees
Apr 12 - Apr 13
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
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 ￥12,853
￥24,301 total
includes taxes & fees
Apr 5 - Apr 6
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, (18 reviews)
"Amazing place very happy will stay again 10 stars "
United States
Dean S.
The price is ￥14,677
￥28,041 total
includes taxes & fees
Apr 5 - Apr 6
Cozy Cabin in a Rural Setting #16 near Temple,NH
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 ￥25,525
￥45,870 total
includes taxes & fees
Apr 5 - Apr 6
Cottage beside a waterfall
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 ￥17,612
￥31,225 total
includes taxes & fees
Apr 15 - Apr 16
Cozy Cabin in a rural setting (#10) In Temple, NH
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 ￥23,930
￥69,128 total
includes taxes & fees
Apr 15 - Apr 16
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 ￥31,471
￥46,967 total
includes taxes & fees
Apr 16 - Apr 17
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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, (27 reviews)
"Great family spot. Very clean and comfortable. Convenient to local attractions and shopping. "
United States
Dennyse M.
The price is ￥35,894
￥81,902 total
includes taxes & fees
Apr 6 - Apr 7
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
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 ￥39,252
￥62,668 total
includes taxes & fees
Apr 19 - Apr 20
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 ￥25,525
￥45,870 total
includes taxes & fees
Apr 5 - Apr 6
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, (15 reviews)
"Charming location and beautiful setting. "
United States
Cherie G.
The price is ￥22,175
￥33,408 total
includes taxes & fees
Apr 5 - Apr 6
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
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 ￥30,159
￥47,435 total
includes taxes & fees
Apr 19 - Apr 20
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Fridge, microwave, oven, stovetop

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)
"Nice house in a nice location. "
United States
Rob B.
The price is ￥23,052
￥47,687 total
includes taxes & fees
Apr 6 - Apr 7
Modern Downtown 12ppl Hot Tub Fire Pit Games
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 ￥26,585
￥55,872 total
includes taxes & fees
Apr 12 - Apr 13
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
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)
"Host was wonderful and very accommodating! Home was very welcoming and comfortable. Highly recommend!"
United States
Robin Q.
The price is ￥32,305
￥63,957 total
includes taxes & fees
Apr 12 - Apr 13
Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School
Exterior

Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
10.0 out of 10, Exceptional, (3 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
The price is ￥18,665
￥23,714 total
includes taxes & fees
Apr 5 - Apr 6
Central Large 2-bedrooms with office in Keene
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, (2 reviews)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
The price is ￥30,630
￥74,603 total
includes taxes & fees
Apr 14 - Apr 15
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Exterior

2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is ￥76,447
￥114,449 total
includes taxes & fees
Apr 5 - Apr 6
2 Cabins & Sauna on Lake Monomonac
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

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

6/10 Okay
"So-so hotel for the price but location is very good."
eugene 2-night trip
Posted 1 day 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:

  • 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 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 Militia Training Field are a couple of lovely local spots to get outside and enjoy nature. Lake Dennison State Recreation Area and Blueberry Island 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.