Winchendon Holiday Rentals from €163: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Winchendon has to offer?

Modern Waterfront Gem w/ Dock on Lake Monomonac : This highly rated holiday home rental in Winchendon is located on a lake, and has a selection of games, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, kitchenware and a coffee maker.

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Holiday Rentals in Winchendon

Our top choices for Winchendon holiday rentals

"Me and my children had an amazing time exploring the lake."

Fridge, coffee/tea maker, toaster, cookware/dishes/utensils

"Beautiful cottage on the lake. Everything seams new and spotless. Would definitely stay again."

"This comfortable 2-bedroom house on a tranquil NH pond was the perfect weekend escape! We absolutely loved the peaceful setting and beautiful views. It was incredibly relaxing and exactly what we needed. Highly recommend!"

includes taxes & fees

2 Sept - 3 Sept

"Very nice, clean, and great area. We enjoyed it very much!"

"Great property close to where we needed to be."

"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "

includes taxes & fees

21 Aug - 22 Aug

"The cabin itself was okay. Could have been cleaner and if we had stayed more than one night I would have said something. Mold in shower, crumbs under microwave, dusty windowsills. No top sheet on bed. The area surrounding was just dirt and gravel and a couple of ugly outbuildings with junk all around. The cabins themselves looked fine but otherwise was not pretty"

includes taxes & fees

21 Aug - 22 Aug

"It was a cute nice space. Close to outlets and plenty of trails for hiking. The cabin was also just a nice space to relax."

includes taxes & fees

21 Aug - 22 Aug

"We really enjoyed our time at the lake house! The deck and fire pit was fun and everything was very nicely decorated and had enough supplies to make it very easy and a quiet peaceful setting!"

"Property was clean and super close to the downtown square! "

includes taxes & fees

26 Aug - 27 Aug

"Beautiful place"

"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."

includes taxes & fees

28 Aug - 29 Aug

3 bedrooms, travel cot, free WiFi, bed sheets

"We really appreciated the solitude and quiet retreat this cabin offered. "

"What an absolutely charming place!! It was so lovely staying here. This place is exactly what we wanted... a little weekend escape not too far from home, nestled in the woods. Absolutely beautiful. The hosts were so kind, too!"

includes taxes & fees

9 Sept - 10 Sept

"We really enjoyed our stay. The seating outside was lovely!"

"What a unique place to stay with a waterfall in the backyard! Quiet, beautiful grounds on the property. Clean, private and well appointed. "

includes taxes & fees

28 Aug - 29 Aug

"Ryan’s property is beautiful and peaceful. Its exactly what I would describe as a perfect summer getaway."

"It was a great place for what I needed. I was working in the area and it was a great quiet location, with nice scenery. The place was clean and spacious, with plenty of space to cook. I would definitely stay here again."

"Very clean, well equipped and thoughtfuly supplied. An extra bonus were the great assortment of books, games, movies, and puzzles available. A great deal of experience and generosity went into choices made, and it was much appreciated. "

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Top Winchendon Hotel Reviews

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent

"I like the bed comfort and the tv!!"

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

10/10 Excellent

"Seamless & Stunning—A Perfect Getaway! Our experience was flawless from start to finish. Before check-in, we received a detailed house guide with everything we could possibly need to know. After arrival, Guy checked in to make sure we settled in smoothly. The property is even more beautiful in person—very private, with photos that don’t do it justice. The enormous deck was a highlight, complete with gates that gave us peace of mind when relaxing outside after dark (no unwanted critter visits!). The pond is serene and full of fish—I caught a small pike on my first cast, and my son reeled in a 15-inch largemouth bass! We highly recommend this property and will absolutely be booking again. "

Find out more about Winchendon

Everything you need to know about Winchendon holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchendon holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchendon holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchendon holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchendon holiday rentals we have selected for you start as low as €163 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchendon rentals

At Expedia, we put the best Winchendon holiday 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 holiday.

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.

Frequently asked questions

Are there holiday rentals in Winchendon?

Yes, there are holiday rentals close to the most popular sights in Winchendon, or you can select a more secluded option if you're looking for a relaxing stay. Winchendon is known for its parks.

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

Modern Waterfront Gem w/ Dock on Lake Monomonac: This highly rated holiday home rental in Winchendon is located on a lake, and has a selection of games, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, kitchenware and a coffee maker.

How many holiday rentals will I find in Winchendon?

Choose from 6 Expedia holiday rentals in Winchendon for a memorable holiday.

What’s there to see and do in Winchendon?

Lake Dennison State Recreation Area and Millers River are a couple of scenic spots to enjoy the outdoors, whereas The Robinson-Broadhurst Foundation Performing Arts Ampitheater is one of the cultural attractions. V F W Park and Blueberry Island are other places to visit while you're in town.

What’s a holiday rental in Winchendon like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchendon. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip.

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Holiday Rentals in Winchendon

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Holiday Rentals in Winchendon

Our top choices for Winchendon holiday rentals

Cozy Lakefront Cottage

Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Cozy Updated Log Cabin with Mountain Views close to Monadnock

Modern Mid-Century in Fitchburg

Downtown Hot Tub Escape

Cozy Cabin in a Rural setting #8

Cozy Cabin in a Rural setting-14

Quiet private pond getaway

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

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

River Room overlooking the waterfall

Charming Waterfront Log Cabin

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

2 queen and 2 twin beds

Cottage beside a waterfall

Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

Top Winchendon Hotel Reviews

Great Wolf Lodge Boston / Fitchburg, MA

Keene Elm City Hotel, Ascend Hotel Collection

Best Western Plus Keene Hotel

The Colonial Hotel

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Fairfield Inn & Suites by Marriott Keene Downtown

The Burrell House

Doubletree by Hilton Hotel Leominster

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Find out more about Winchendon

Frequently asked questions