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

Winchendon Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winchendon vacation rentals

A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

1. 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, (10 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.
$367 nightly
The price is $388
Oct 18 - Oct 19
Total with taxes and fees
Enjoy your stay in an antique home in an antique toy museum!
A house by a lake with a dock and a boat.

2. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (13 reviews)
"Jim was a great host very friendly and welcoming, the cabin is in the perfect spot on the lake and we were able to see a fireworks show directly on the dock, thank you !"
United States
clifford t.
$265 nightly
The price is $288
Oct 20 - Oct 21
Total with taxes and fees
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A small, single-story house with a front door open, revealing a kitchen area with a sink and cabinets.

3. Cozy Cabin in a rural setting #12 in Temple NH

Cozy Cabin in a rural setting #12 in Temple NH
Temple
9.2 out of 10, Wonderful, (25 reviews)
"Amazing best place in nh"
United States
Dean S.
$193 nightly
The price is $209
Oct 18 - Oct 19
Total with taxes and fees
Cozy Cabin in a rural setting #12 in Temple NH
A lakeside park with picnic tables and a concrete walkway.

4. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
$75 nightly
The price is $81
Oct 17 - Oct 18
Total with taxes and fees
2 private mountain RV pads for rent. Full hook ups
A modern bathroom with a shower, a small shelf with toiletries, and a kitchen area visible through an open door.

5. Cozy Cabin in a Rural setting #8

Cozy Cabin in a Rural setting #8
Temple
8.4 out of 10, Very good, (5 reviews)
"The cabin interiors were something out of a Manhattan boutique hotel. Brand new stylish furnishings"
United States
James M.
$183 nightly
The price is $199
Oct 18 - Oct 19
Total with taxes and fees
Cozy Cabin in a Rural setting #8
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

6. 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, (47 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
$189 nightly
The price is $205
Nov 9 - Nov 10
Total with taxes and fees
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A house with a stone wall and a dock extending into a calm body of water.

7. 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, (42 reviews)
"Very clean and tidy!Tyler was great - even accommodated last minute to add our dogs to the booking!Would definitely stay again!"
United States
Christina C.
$361 nightly
The price is $396
Oct 18 - Oct 19
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
A wooden deck with outdoor furniture, a white door, and windows.

8. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Rindge
10.0 out of 10, Exceptional, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
$361 nightly
The price is $392
Oct 22 - Oct 23
Total with taxes and fees
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A cabin with a covered porch, large windows, and snow-covered ground.

9. 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.
$282 nightly
The price is $306
Oct 19 - Oct 20
Total with taxes and fees
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A black-framed door with a glass panel, leading into a hallway with wooden flooring and white walls.

10. Cozy Cabin in a Rural setting-14

Cozy Cabin in a Rural setting-14
Temple
9.4 out of 10, Exceptional, (12 reviews)
"The experience was exemplary, and I would certainly consider staying at this property again should my travels return me to New Hampshire."
United States
Anghy
$216 nightly
The price is $234
Oct 18 - Oct 19
Total with taxes and fees
Cozy Cabin in a Rural setting-14
A cabin with a dock extending into a calm river, surrounded by snow-covered trees and a clear sky.

11. 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)
"Awesome few days away great place and surroundings. Jim is always there for you ."
United States
David S.
$334 nightly
The price is $363
Oct 19 - Oct 20
Total with taxes and fees
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A bedroom with a bed, a bedside table, and a nightstand. There is a window with blinds and a door leading to the outside.

12. 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, (20 reviews)
"Great place"
United States
Ann S.
$181 nightly
The price is $196
Oct 18 - Oct 19
Total with taxes and fees
Cozy Cabin in a rural setting #10 In Temple, NH
A stone pathway leading to a large, multi-story building surrounded by trees and shrubs.

13. Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful cabin and grounds! Very quiet, and the cabin is full of cool stuff artists have left behind. 10/10 :)."
United States
Ryan B.
$265 nightly
The price is $288
Oct 18 - Oct 19
Total with taxes and fees
Cottage beside a waterfall
A bedroom with a bed, a nightstand, a ceiling fan, and three windows with blinds.

14. Fitchburg hideaway Home

Fitchburg hideaway Home
Fitchburg
$215 nightly
The price is $240
Oct 27 - Oct 28
Total with taxes and fees
Fitchburg hideaway Home
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

15. "Pondlife" - Waterfront home in a peaceful, wooded setting.

"Pondlife" - Waterfront home in a peaceful, wooded setting.
Fitzwilliam
10.0 out of 10, Exceptional, (4 reviews)
"We absolutely loved our stay. Great location, very clean, well decorated and all the essentials you could possibly need. The host was warm and responsive. Beautiful view of the pond. We highly recommend this lovely home."
United States
Sandra O.
$273 nightly
The price is $296
Oct 18 - Oct 19
Total with taxes and fees
"Pondlife" - Waterfront home in a peaceful, wooded setting.
A modern living room with a fireplace, a mounted TV, and a leather couch.

16. 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, (27 reviews)
"Great experience"
United States
Dalton
$230 nightly
The price is $250
Oct 25 - Oct 26
Total with taxes and fees
Cozy Cabin in a Rural Setting #16 near Temple,NH
A stone pathway leading to a rustic building with a steep roof, surrounded by autumn foliage and a stone wall.

17. River Room overlooking the waterfall

River Room overlooking the waterfall
Wilton
10.0 out of 10, Exceptional, (7 reviews)
"Couldn't ask for a lovelier place to spend a couple of days in New Hampshire in May!"
United States
Bob H.
$256 nightly
The price is $278
Oct 18 - Oct 19
Total with taxes and fees
River Room overlooking the waterfall
A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

18. 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, (37 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
$468 nightly
The price is $513
Oct 22 - Oct 23
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A two-story house with a front porch, a staircase, and a small garden area.

19. Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
9.6 out of 10, Exceptional, (9 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
$155 nightly
The price is $168
Oct 19 - Oct 20
Total with taxes and fees
Central Large 2-bedrooms with office in Keene
A modern living room with a wooden door, a sofa, a dining table with chairs, and a mounted TV.

20. Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.
Dublin
10.0 out of 10, Exceptional, (5 reviews)
"Very nice well kept and a great location to Monadnock Hospital."
United States
Melissa M.
$294 nightly
The price is $315
Nov 1 - Nov 2
Total with taxes and fees
Cozy Tiny House on Main Street. Fully Renovated.
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Excellent stay"
Lisa 1-night trip
Posted 2 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

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 $196 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 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 6 Expedia vacation rentals in Winchendon for a memorable vacation.

What’s there to see and do in Winchendon?

Wendall P. Clark Memorial and Hyde Park 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.