Find Hotels with a Pool in Winchendon, MA

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Check availability on Winchendon Hotels with a Pool

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Winchendon hotels with a pool

WiFi, bed sheets
Spacious lakeside 4-bedroom house in beautiful Ashburnham

Spacious lakeside 4-bedroom house in beautiful Ashburnham

Spacious lakeside 4-bedroom house in beautiful Ashburnham
2.0 star property
Ashburnham
The price is ￥24,979
￥47,855 total
includes taxes & fees
Dec 25 - Dec 26
Spacious lakeside 4-bedroom house in beautiful Ashburnham
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, (967)
"The room was perfect, and the food was great "
United States
Paul
The price is ￥18,391
￥19,954 total
includes taxes & fees
Dec 29 - Dec 30
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool, open 6:00 AM to 10:00 PM, sun 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 ￥21,701
￥23,546 total
includes taxes & fees
Dec 29 - Dec 30
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, (1002)
"Easy checkin, pleasant staff and clean room. "
United States
Susan
The Colonial Hotel
Indoor pool, open 8:00 AM to 10:00 PM, sun 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 ￥20,483
￥22,879 total
includes taxes & fees
Dec 30 - Dec 31
Doubletree by Hilton Hotel Leominster
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 ￥26,284
￥28,518 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn & Suites Keene
Water park
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, (1005)
"Nice place "
United States
Daniel
The price is ￥25,150
￥28,093 total
includes taxes & fees
Jan 22 - Jan 23, 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, (1002)
"Very comfortable and clean."
United States
Christina
The price is ￥28,102
￥30,491 total
includes taxes & fees
Dec 30 - Dec 31
Courtyard by Marriott Keene Downtown
Outdoor spa tub
Downtown Hot Tub Escape

Downtown Hot Tub Escape

Downtown Hot Tub Escape
Keene
9.6 out of 10, Exceptional, (21)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is ￥22,559
￥46,667 total
includes taxes & fees
Dec 30 - Dec 31
Downtown Hot Tub Escape
Garden
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

Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"Perfect...they let me check in early too at no charge "
PAUL 1-night trip
Posted 2 days ago
Motel 6 Leominster, MA

Frequently asked questions

What are some hotels with pools in Winchendon?
Cozy Lakefront Cottage: Provides kitchens, a pool, and Smart TVs. Modern Waterfront Gem w/ Dock on Lake Monomonac: Resort, 9-minute walk from Great Wolf Lodge Waterpark. Features 4 indoor pools, a children's pool, and free water-park access. Great Wolf Lodge Boston / Fitchburg, MA: Offers 2 restaurants, an indoor pool, and free self parking. Doubletree by Hilton Hotel Leominster: Provides a sauna, an indoor pool, and free self parking. The Colonial Hotel: Offers buffet, an indoor pool, and complimentary 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 Millers River. During your stay, check out 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 into account the local weather in Winchendon is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchendon are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.