Search Hotels with Pool in Winchendon

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Check availability on Winchendon Hotels with Pool

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winchendon hotels with a pool

Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very good, (968)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is ฿3,661
฿3,972 total
includes taxes & fees
29 Dec - 30 Dec
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers
Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
4.0 star property
Leominster
8.6 out of 10, Excellent, (1001)
"The hotel was very nice and the restaurant was a nice establishment. "
United States
Dina
The price is ฿4,052
฿4,526 total
includes taxes & fees
30 Dec - 31 Dec
Doubletree by Hilton Hotel Leominster
Indoor pool, open 6:00 AM to 10:00 PM, pool loungers
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1001)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ฿4,319
฿4,686 total
includes taxes & fees
29 Dec - 30 Dec
Best Western Plus Keene Hotel
Indoor pool
The Colonial Hotel

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1000)
"Easy checkin, pleasant staff and clean room. "
United States
Susan
The Colonial Hotel
Indoor pool
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (358)
"Clean comfy nice staff "
United States
Katherine
The price is ฿5,118
฿5,553 total
includes taxes & fees
25 Jan - 26 Jan 2026
Hampton Inn & Suites Keene
4 indoor pools, seasonal outdoor pool, pool cabanas (surcharge)
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1007)
"The room was clean, the staff was very nice!"
United States
Entela
The price is ฿5,006
฿5,592 total
includes taxes & fees
25 Jan - 26 Jan 2026
Great Wolf Lodge Boston / Fitchburg, MA
Indoor pool
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1001)
"Very comfortable and clean."
United States
Christina
The price is ฿5,593
฿6,069 total
includes taxes & fees
16 Jan - 17 Jan 2026
Courtyard by Marriott Keene Downtown
Outdoor pool
Howarth House B&B

Howarth House B&B

Howarth House B&B
3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (110)
"Beautiful place, great hospitality! "
United States
andrew
Howarth House B&B
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

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent
"Everything "
Karen 1-night trip
Posted 4 days ago
Great Wolf Lodge Boston / Fitchburg, MA

Frequently asked questions

What are some hotels with pools in Winchendon?
Modern Waterfront Gem w/ Dock on Lake Monomonac: Provides kitchens, a pool and Smart televisions. Great Wolf Lodge Boston / Fitchburg, MA: Resort, 9-minute walk from Great Wolf Lodge Waterpark. Offers 4 indoor swimming pools, a children's pool and free water park access. The Colonial Hotel: Provides a sauna, an indoor pool and free self parking. Motel 6 Leominster, MA: Offers 2 restaurants, an indoor pool and free self parking. Doubletree by Hilton Hotel Leominster: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access.
What is there to see and do in Winchendon?
Spend some time experiencing the great outdoors at Wendall P. Clark Memorial and Hyde Park. During your stay, visit sights such as Lake Dennison State Recreation Area, Winchendon Town Hall and Otter River State Forest.
When is the best time to book a hotel with a pool in Winchendon?
Taking the local weather in Winchendon into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchendon are January, March, February and November, with each month seeing an average of 19 cm of snowfall.