Winchendon Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Winchendon

Exterior
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Cottage in Westminster

9.6 out of 10, Exceptional, (29)
"Nice location and a very cool place to stay "
United States
Samson M.
$341 nightly
The price is $374
Dec 9 - Dec 10
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Exterior detail
Cozy Cabin in a Rural setting #8

Cabin in Temple

9.0 out of 10, Wonderful, (4)
"Cute, cozy and clean. "
United States
Jessica F.
Cozy Cabin in a Rural setting #8
Fridge, microwave, oven, stovetop
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Apartment in Peterborough

9.8 out of 10, Exceptional, (29)
"I had a great stay at Mary Anne and Ben’s place in Peterborough. The apartment was clean and comfortable, and the location cannot be beat."
United States
Joseph K.
$129 nightly
The price is $139
Dec 7 - Dec 8
Total with taxes and fees
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Cabin in Fitzwilliam

10.0 out of 10, Exceptional, (13)
"Loved the area"
United States
Jose R.
$192 nightly
The price is $208
Dec 7 - Dec 8
Total with taxes and fees
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
1 bedroom, free WiFi, bed sheets
Cozy Cabin in a Rural setting-14

Cabin in Temple

9.4 out of 10, Exceptional, (8)
"A wonderful little cabin. Everything was as cute and clean as the pictures and descriptions. You will love this place!"
United States
Craig
Cozy Cabin in a Rural setting-14
Exterior
Cozy Cabin in a rural setting (#10) In Temple, NH

Cabin in Temple

9.0 out of 10, Wonderful, (19)
"Nice little cabin, clean other cabins are a little close other than that everything was fine "
United States
Lisa G.
Cozy Cabin in a rural setting (#10) In Temple, NH
Property grounds
Cottage beside a waterfall

Cottage in Wilton

9.8 out of 10, Exceptional, (10)
"What a unique place to stay with a waterfall in the backyard! Quiet, beautiful grounds on the property. Clean, private and well appointed. "
United States
Marcella J.
$265 nightly
The price is $288
Dec 5 - Dec 6
Total with taxes and fees
Cottage beside a waterfall
Terrace/patio
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Cottage in Rindge

10.0 out of 10, Exceptional, (22)
"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.
$331 nightly
The price is $359
Dec 7 - Dec 8
Total with taxes and fees
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Fridge, microwave, oven, stovetop
Downtown Hot Tub Escape

Vacation Home in Keene

9.6 out of 10, Exceptional, (21)
"Nice house in a nice location. "
United States
Rob B.
$256 nightly
The price is $277
Dec 7 - Dec 8
Total with taxes and fees
Downtown Hot Tub Escape
Fridge, microwave, oven, stovetop
Modern 3BR Near FSU • 15 Min to Wachusett

Apartment in Fitchburg

10.0 out of 10, Exceptional, (12)
"Wonderful place to stay. Everything was very clean, comfortable, and spacious, with a warm, welcoming feel. I highly recommend the place to stay. "
United States
Catherine
$309 nightly
The price is $314
Dec 11 - Dec 12
Total with taxes and fees
Modern 3BR Near FSU • 15 Min to Wachusett
Smart TV
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Cabin in Westminster

10.0 out of 10, Exceptional, (23)
"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. "
United States
Michael T.
$468 nightly
The price is $513
Dec 11 - Dec 12
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Interior
Charming cabin in delightful Greenfield New Hampshire with WiFi access

Cabin in Greenfield

9.8 out of 10, Exceptional, (8)
"Its was great clean, quite and comfortable. "
United States
John G.
$243 nightly
The price is $264
Dec 6 - Dec 7
Total with taxes and fees
Charming cabin in delightful Greenfield New Hampshire with WiFi access
Outdoor dining
River Room overlooking the waterfall

Apartment in Wilton

10.0 out of 10, Exceptional, (3)
"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.
$265 nightly
The price is $288
Dec 5 - Dec 6
Total with taxes and fees
River Room overlooking the waterfall
Property grounds
Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School

Apartment in Wilton

2.0 star property
10.0 out of 10, Exceptional, (1)
"Christine was so personally welcoming. Was flying into Boston on the red eye and needed to check in early and she not only accommodated that request, she left us pancake mix, local maple syrup, butter and a fresh carton of half and half for coffee for our early morning. The amenities were all top notch. I’m a big fan of doterra essentials so it was nice to see them being used. "
United States
Joseph C.
$344 nightly
The price is $373
Dec 7 - Dec 8
Total with taxes and fees
Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School
Fridge, microwave, stovetop, coffee/tea maker
Cozy Cabin in a Rural Setting #16 near Temple,NH

Cabin in Temple

9.4 out of 10, Exceptional, (17)
"Super cute cabin with updated features and it was cozy and recently updated. The bed was particularly comfortable and the efficient layout made it possible for four adults to stay. Parking was easy and checkin and communication with the host was excellent before and after our stay. Would highly reccommend!"
United States
Kevin H.
Cozy Cabin in a Rural Setting #16 near Temple,NH
Interior
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Vacation Home in Dublin

10.0 out of 10, Exceptional, (25)
"Good place to stay during a wedding week"
United States
Veronique S.
$541 nightly
The price is $572
Dec 7 - Dec 8
Total with taxes and fees
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Interior
Entire private apartment suite in home with own entrance, views and private gym.

Apartment in Keene

$336 nightly
The price is $364
Dec 15 - Dec 16
Total with taxes and fees
Entire private apartment suite in home with own entrance, views and private gym.
Outdoor dining
Charming Home Walk to Downtown!

Vacation Home in Keene

10.0 out of 10, Exceptional, (2)
"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.
$599 nightly
The price is $650
Dec 8 - Dec 9
Total with taxes and fees
Charming Home Walk to Downtown!
Terrace/patio
Unique Cozy private 1-bedroom apartment in charming Temple

Apartment in Temple

9.8 out of 10, Exceptional, (7)
"very clean, well decorated, comfortable and peaceful"
United States
Dan G.
$400 nightly
The price is $434
Dec 9 - Dec 10
Total with taxes and fees
Unique Cozy private 1-bedroom apartment in charming Temple
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
"Very clean. Staff was friendly. "
Bryan 1-night trip
Posted 2 days ago
Doubletree by Hilton Hotel Leominster

Find out more about Winchendon

Everything you need to know about Winchendon vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchendon vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchendon vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchendon vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchendon. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchendon in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $264 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchendon rentals

At Expedia, we put the best Winchendon vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchendon rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchendon vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchendon. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Winchendon?

Yes, we offer vacation rentals near well known points of interest in Winchendon, or you can choose a secluded option if you're looking for relaxation. 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 5 Expedia vacation rentals in Winchendon for a memorable vacation.

What’s there to see and do in Winchendon?

Wendall P. Clark Memorial and Militia Training Field 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 Winchendon Town Hall 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.