The Best Hotels with a Pool in Winchendon, MA from NT$4,156 in 2026

Q: What are some hotels with pools in Winchendon?

Great Wolf Lodge Boston / Fitchburg, MA : Features kitchens, a pool, and Smart TVs. The Colonial Hotel : Resort steps from Great Wolf Lodge Waterpark. Offers 4 indoor pools, a children's pool, and free water-park access. Keene Elm City Hotel, an Ascend Collection Hotel : Provides a sauna, an indoor pool, and free self parking. Doubletree by Hilton Hotel Leominster : Features buffet, an indoor pool, and complimentary wired internet access. Best Western Plus Keene Hotel : Offers 2 restaurants, an indoor pool, and free self parking.

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Our top choices for Winchendon hotels with a pool

Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Splash into comfort at this indoor pool oasis offering year-round aquatic escape in Keene.

NT$4,156 total

includes taxes & fees

Jul 13 - Jul 14

Great Wolf Lodge Boston / Fitchburg, MA

Fitchburg

A splashing wonderland awaits with 4 indoor pools, seasonal outdoor oasis, and a lazy river to float away your cares.

NT$5,893 total

includes taxes & fees

Jul 14 - Jul 15

Indoor pool, open 6:00 AM to 10:00 PM, sun loungers

Best Western Plus Keene Hotel

Keene

Splash into luxury at this hotel's sparkling indoor pool, complete with plush sun loungers and serene atmosphere.

NT$4,163 total

includes taxes & fees

Aug 2 - Aug 3

The Colonial Hotel

Gardner

Dive into a serene indoor pool retreat with hot tub and sauna, perfect for year-round relaxation near Wachusett Mountain.

NT$5,499 total

includes taxes & fees

Jul 19 - Jul 20

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

Doubletree by Hilton Hotel Leominster

Leominster

Dive into a refreshing mountain escape with an indoor pool sanctuary that's open from morning till night in this peaceful retreat.

NT$6,015 total

includes taxes & fees

Jul 26 - Jul 27

Hampton Inn & Suites Keene

Keene

Splash into serenity at this inviting indoor pool hotel, where year-round swimming meets complete comfort and relaxation.

NT$5,556 total

includes taxes & fees

Jul 20 - Jul 21

Courtyard by Marriott Keene Downtown

Keene

Dive into the year-round aquatic escape at this art deco hotel with a pristine indoor pool.

NT$6,601 total

includes taxes & fees

Jul 14 - Jul 15

Howarth House B&B

Fitchburg

Splash into bliss with private pools and outdoor hot tubs at this charming B&B retreat.

NT$6,808 total

includes taxes & fees

Jul 14 - Jul 15

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Breakfast included

4 stars

Top Winchendon Hotel Reviews

Best Western Plus Keene Hotel

10/10 Excellent

"Front desk staff extremely helpful. The property interior and exterior was very well maintained. One of the best Best Western hotels I’ve stayed at."

Doubletree by Hilton Hotel Leominster

8/10 Good

"Clean room (looked recently updated/renovated); helpful staff; 1 of our keys did not work upon arrival so had to go back to the front desk and get new ones. Pool was small, and not really “heated” - the room it was was definitely warm/humid but the water felt cool. Very convenient location off the highway!"

Frequently asked questions

What are some hotels with pools in Winchendon?

Great Wolf Lodge Boston / Fitchburg, MA: Features kitchens, a pool, and Smart TVs. The Colonial Hotel: Resort steps from Great Wolf Lodge Waterpark. Offers 4 indoor pools, a children's pool, and free water-park access. Keene Elm City Hotel, an Ascend Collection Hotel: Provides a sauna, an indoor pool, and free self parking. Doubletree by Hilton Hotel Leominster: Features buffet, an indoor pool, and complimentary wired internet access. Best Western Plus Keene Hotel: Offers 2 restaurants, 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, check out 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 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.

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Our top choices for Winchendon hotels with a pool