Winchendon Holiday Rentals, Massachusetts: Private House Rentals

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

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Go beyond your typical stay in Winchendon

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Our top choices for Winchendon hotels

Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

Presidential Suite, 1 King Bed, Non Smoking | Living area | 55-inch flat-screen TV with cable channels, TV, Netflix

1. Doubletree by Hilton Hotel Leominster

Leominster

Elizabeth

4.020.184 ₫

4.490.546 ₫ total

includes taxes & fees

27 Sept - 28 Sept

Standard Room, 1 King Bed, Non Smoking | In-room safe, desk, iron/ironing board, free cots/infant beds

2. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Ingrid

3.676.998 ₫

3.989.673 ₫ total

includes taxes & fees

3 Sept - 4 Sept

3. Motel 6 Leominster, MA

Leominster

Linda

2.072.899 ₫

2.367.584 ₫ total

includes taxes & fees

3 Sept - 4 Sept

4. The Colonial Hotel

Gardner

zavean

3.988.630 ₫

4.455.426 ₫ total

includes taxes & fees

31 Aug - 1 Sept

5. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

James

4.522.792 ₫

4.907.229 ₫ total

includes taxes & fees

6 Sept - 7 Sept

Premium bedding, desk, laptop workspace, blackout curtains

6. Best Western Plus Keene Hotel

Keene

Julia

3.885.622 ₫

4.216.030 ₫ total

includes taxes & fees

30 Aug - 31 Aug

In-room safe, desk, blackout curtains, iron/ironing board

7. Days Inn by Wyndham Keene NH

Keene

Alex

2.527.704 ₫

2.742.559 ₫ total

includes taxes & fees

9 Sept - 10 Sept

8. Gardner Inn

Gardner

Vicki

2.581.722 ₫

2.883.705 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Guesthouse B | Premium bedding, pillow-top beds, desk, laptop workspace

9. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

James

3.966.464 ₫

4.586.299 ₫ total

includes taxes & fees

13 Sept - 14 Sept

10. Chocksett Inn and Restaurant

Sterling

Beth

4.146.402 ₫

4.631.453 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Deluxe Double Room, 1 Queen Bed | Premium bedding, laptop workspace, soundproofing

Deluxe Double Room | Private kitchenette | Coffee/tea maker, mini-fridge, microwave

11. The Burrell House

Keene

Justin

3.272.623 ₫

3.648.975 ₫ total

includes taxes & fees

1 Sept - 2 Sept

Daily cooked-to-order breakfast for a fee

Hypo-allergenic bedding, in-room safe, desk, laptop workspace

12. Courtyard by Marriott Keene Downtown

Keene

Deborah

4.411.939 ₫

4.786.954 ₫ total

includes taxes & fees

6 Sept - 7 Sept

13. Hampton Inn & Suites Keene

Keene

Christopher

4.012.883 ₫

4.353.978 ₫ total

includes taxes & fees

8 Sept - 9 Sept

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

14. The Maguire House Bed & Breakfast

Ashburnham

Ranjit

7.432.230 ₫

7.432.230 ₫ total

includes taxes & fees

3 Sept - 4 Sept

North Superior Room, 1 Queen Bed, Garden View | Premium bedding, laptop workspace, iron/ironing board, free WiFi

15. Howarth House B&B

Fitchburg

David

5.515.497 ₫

5.515.497 ₫ total

includes taxes & fees

31 Aug - 1 Sept

16. The Carriage Barn Inn

Keene

Jonathan

3.810.725 ₫

4.134.636 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Traditional Room, 1 Bedroom, Accessible | Premium bedding, laptop workspace, free WiFi, individually decorated

17. The Birchwood Inn

Temple

Karen

4.563.650 ₫

4.951.691 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Standard Room, 1 King Bed, Non Smoking | Free WiFi, alarm clocks, bed sheets

18. Econo Lodge

Westminster

Sherry

2.859.453 ₫

3.136.820 ₫ total

includes taxes & fees

27 Sept - 28 Sept

19. Monadnock Inn

Jaffrey

Saif

4.403.531 ₫

4.777.750 ₫ total

includes taxes & fees

30 Aug - 31 Aug

20. Centennial House

Northfield

Amy

4.680.428 ₫

4.947.212 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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Stay near popular Winchendon attractions

Lake Dennison State Recreation Area

10.0/10 (1 review)

This serene 85-acre lake offers swimming, fishing, and access to 50+ miles of mountain biking trails. Reserve one of the 150 wooded campsites early for a prime lakeside spot to fully experience this natural retreat.

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Blueberry Island

Blueberry Island sits privately in Lake Monomonac, spanning the NH-MA border. While enjoying the lake's recreational offerings, respect the island's residential nature and focus on surrounding public areas instead.

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Winchendon Community Park

Winchendon Community Park offers a picturesque amphitheatre for concerts and community events during warmer months. Enjoy dog-friendly trails before settling in for performances under the stars.

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Winchendon Town Hall

The Winchendon Municipal Building serves as the town's administrative centre. Visitors can observe civic operations during business hours and occasionally attend public meetings.

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Monument Park

Monument Park is just one of the places to see in Winchendon, so why not enjoy the other things to explore during your travels? While you're in the area, wander around the parks.

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Wetmore Trailhead

Wetmore Trailhead opens to miles of serene forest and wetland paths in Birch Hill Wildlife Management Area. Bring sturdy shoes and binoculars for spotting native birds along the well-maintained trails.

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Hyde Park

Explore the great outdoors at Hyde Park, a lovely green space in Winchendon. While you're in the area, wander around the parks.

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Beals Memorial Library

This historic library houses literary treasures and sensory-friendly programmes for neurodivergent visitors. Browse the collection, join a book club, or borrow unique items from their "Library of Things" like telescopes.

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Learn more about Winchendon

Toy Town's charm comes alive at the Old Murdock Senior Centre, where the town's unique toy-making history is celebrated. Lake Dennison Recreation Area offers perfect summer swimming, while winter visitors can explore nearby Wachusett Mountain for skiing in Princeton.

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A river reflecting autumn trees and a dense forest.

Top Winchendon Hotel Reviews

Days Inn by Wyndham Keene NH

8/10 Good

"The staff was helpful. Parking was easy. It was an ok stay. I would stay there again for the price."

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good

"Has everything necessary for a two night stay."

Doubletree by Hilton Hotel Leominster

10/10 Excellent

"Breakfast was great and the servers were great."

The Colonial Hotel

10/10 Excellent

"The property was excellent. Loved the pool and hot tub."

Econo Lodge

10/10 Excellent

"Room was surprisingly clean Staff was exceptionally helpful Wall unit air conditioning was good and easy to use The hotel was convenient to route 2 State HWY Easy and central to my relatives and friends, restaurants also They do not include breakfast as this motel is not set up for that. Excellent accommodations if you intend to spend mainly sleep time their."

Riverhouse by Weekender (Formerly Jack Daniels Inn)

8/10 Good

"Quiet."

Gardner Inn

10/10 Excellent

"My room was clean and comfortable. The staff was excellent and very responsive to any and all requests and to even just chat with. Plenty of parking with a special spot for a Veteran - Because We Served - to park."

The Burrell House

10/10 Excellent

"Short walk to everything."

Courtyard by Marriott Keene Downtown

10/10 Excellent

"Everything was great!! Beds were super comfortable."

More cheap stays in Winchendon