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

Hotels with Pool & Resorts in Winchendon from AU$209

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Check availability on Winchendon Hotels with Pool

Our top choices for Winchendon hotels with a pool

Waterslide

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1,028 reviews)
  • cleanliness
    A splashing wonderland awaits with 4 indoor pools, seasonal outdoor oasis, and a lazy river to float away your cares.
The price is AU$238
includes taxes & fees
27 July - 28 July
Great Wolf Lodge Boston / Fitchburg, MA
Indoor pool

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Splash into comfort at this indoor pool oasis offering year-round aquatic escape in Keene.
The price is AU$209
includes taxes & fees
26 July - 27 July
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool, open 6:00 AM to 10:00 PM, pool loungers

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Splash into luxury at this hotel's sparkling indoor pool, complete with plush sun loungers and serene atmosphere.
The price is AU$215
includes taxes & fees
26 July - 27 July
Best Western Plus Keene Hotel
Indoor pool

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
9.0 out of 10, Wonderful, (1,016 reviews)
  • cleanliness
    Dive into a serene indoor pool retreat with spa pool and sauna, perfect for year-round relaxation near Wachusett Mountain.
The price is AU$244
includes taxes & fees
10 Aug - 11 Aug
The Colonial Hotel
Indoor pool

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (392 reviews)
  • cleanliness
    Splash into serenity at this inviting indoor pool hotel, where year-round swimming meets complete comfort and relaxation.
The price is AU$240
includes taxes & fees
9 Aug - 10 Aug
Hampton Inn & Suites Keene
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
4.0 star property
Leominster
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Dive into a refreshing mountain escape with an indoor pool sanctuary that's open from morning till night in this peaceful retreat.
The price is AU$280
includes taxes & fees
10 Aug - 11 Aug
Doubletree by Hilton Hotel Leominster
Indoor pool

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Dive into the year-round aquatic escape at this art deco hotel with a pristine indoor pool.
The price is AU$278
includes taxes & fees
2 Aug - 3 Aug
Courtyard by Marriott Keene Downtown
Outdoor pool

Howarth House B&B

Howarth House B&B
3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (116 reviews)
  • cleanliness
    Splash into bliss with private pools and outdoor spa pools at this charming B&B retreat.
The price is AU$302
includes taxes & fees
28 July - 29 July
Howarth House B&B
Fridge, microwave, oven, stovetop

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)
The price is AU$528
includes taxes & fees
21 July - 22 July
Modern Downtown Escape HotTub Fire Pit Games 12ppl
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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Choose what matters most at hotels with a pool in Winchendon

Breakfast included
4 stars

Top Winchendon Hotel Reviews

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Very nice experience, clean, good service, will recommend it"
Maria 3-night trip
Posted 2 hours ago
Best Western Plus Keene Hotel

Frequently asked questions

What are some hotels with pools in Winchendon?
Cozy Lakefront Cottage: Features kitchens, a pool and Smart televisions. Enjoy your stay in an antique home in an antique toy museum!: Resort steps from Great Wolf Lodge Waterpark. Offers 4 indoor swimming pools, a children's pool and free water park access. Great Wolf Lodge Boston / Fitchburg, MA: Provides a sauna, an indoor pool and free self parking. The Colonial Hotel: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Keene Elm City Hotel, an Ascend Collection Hotel: Offers buffet, an indoor pool and free self parking.
What is there to see and do in Winchendon?
Spend some time experiencing the great outdoors at Blueberry Island and Millers River. During your stay, visit sights such as Lake Dennison State Recreation Area, Beals Memorial Library and Winchendon Town Hall.
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.