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
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Winchendon vacation rentals

Interior

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, (9 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 1,437 total
includes taxes & fees
1 Sep - 2 Sep
Enjoy your stay in an antique home in an antique toy museum!
Exterior

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)
"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 724
AED 1,116 total
includes taxes & fees
6 Sep - 7 Sep
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

3. 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.
The price is AED 904
AED 1,387 total
includes taxes & fees
20 Sep - 21 Sep
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Smart TV, fireplace, printers

4. 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, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
The price is AED 645
AED 1,369 total
includes taxes & fees
8 Sep - 9 Sep
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Exterior

5. 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 790
AED 1,248 total
includes taxes & fees
9 Sep - 10 Sep
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

6. 2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is AED 2,090
AED 3,041 total
includes taxes & fees
21 Sep - 22 Sep
2 Cabins & Sauna on Lake Monomonac
Smart TV

7. 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, (25 reviews)
"I would stay here again."
United States
Ann M.
The price is AED 507
AED 857 total
includes taxes & fees
30 Aug - 31 Aug
Cozy Cabin in a Rural Setting #16 near Temple,NH
Exterior detail

8. 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, (21 reviews)
"Amazing best place in nh"
United States
Dean S.
The price is AED 367
AED 686 total
includes taxes & fees
30 Aug - 31 Aug
Cozy Cabin in a rural setting #12 in Temple NH
Property grounds

9. Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (21 reviews)
"BEAUTIFUL surroundings and very peaceful. Would definitely recommend staying here!! "
United States
Vicki L.
The price is AED 588
AED 1,068 total
includes taxes & fees
1 Sep - 2 Sep
Cottage beside a waterfall
Exterior detail

10. 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
10.0 out of 10, Exceptional, (41 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is AED 331
AED 638 total
includes taxes & fees
1 Sep - 2 Sep
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Interior

11. 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 465
AED 752 total
includes taxes & fees
30 Aug - 31 Aug
Cozy Cabin in a Rural setting-14
Smart TV

12. 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
The price is AED 826
AED 1,910 total
includes taxes & fees
1 Sep - 2 Sep
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Exterior

13. 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)
"Beautiful location and perfect for a fishing getaway! House was clean and cozy!"
United States
Julianne R.
The price is AED 735
AED 1,841 total
includes taxes & fees
7 Sep - 8 Sep
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Smart TV

14. 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.
The price is AED 771
AED 1,168 total
includes taxes & fees
15 Sep - 16 Sep
Cozy Tiny House on Main Street. Fully Renovated.
Property grounds

15. River Room overlooking the waterfall

River Room overlooking the waterfall
Wilton
10.0 out of 10, Exceptional, (6 reviews)
"Couldn't ask for a lovelier place to spend a couple of days in New Hampshire in May!"
United States
Bob H.
The price is AED 588
AED 1,068 total
includes taxes & fees
1 Sep - 2 Sep
River Room overlooking the waterfall
Coffee/tea maker, fridge, microwave, oven

16. 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 2,678 total
includes taxes & fees
30 Aug - 31 Aug
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Coffee/tea maker, fridge, microwave, oven

17. 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 621
AED 1,228 total
includes taxes & fees
30 Aug - 31 Aug
Modern Downtown Escape HotTub Fire Pit Games 12ppl
2 bedrooms, iron/ironing board, WiFi, bed sheets

18. Dream Inn LLC 2-bedroom apartment in fabulous Fitchburg with WiFi, fitness room

Dream Inn LLC 2-bedroom apartment in fabulous Fitchburg with WiFi, fitness room
Fitchburg
2.0 out of 10, (2 reviews)
"The stairs to get to the property were inadequate for one member of our party with mobility issues, so we had to cancel. The host was responsive and polite."
United States
Susannah
The price is AED 588
AED 821 total
includes taxes & fees
8 Sep - 9 Sep
Dream Inn LLC 2-bedroom apartment in fabulous Fitchburg with WiFi, fitness room
Exterior

19. Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
9.8 out of 10, Exceptional, (6 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
The price is AED 645
AED 799 total
includes taxes & fees
31 Aug - 1 Sep
Central Large 2-bedrooms with office in Keene
1 bedroom, desk, iron/ironing board, WiFi

20. 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.
The price is AED 406
AED 731 total
includes taxes & fees
2 Sep - 3 Sep
Cozy Cabin in a rural setting #10 In Temple, NH
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
"Breakfast was great and the servers were great."
Manuel 1-night trip
Posted 3 hours ago
Doubletree by Hilton Hotel Leominster

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 Wendall P. Clark Memorial 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.