Search Hotels with Pool in Winchendon

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Check prices for these dates

Tonight
15 Nov - 16 Nov
Tomorrow
16 Nov - 17 Nov
Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov

Our top choices for Winchendon hotels with a pool

A swimming pool with a diving board, lounge chairs, and a sunroof.

1. The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Dive into a serene indoor pool retreat with hot tub and sauna, perfect for year-round relaxation near Wachusett Mountain.
The price is Rp2.620.754
Rp2.927.525 total
includes taxes & fees
16 Nov - 17 Nov
The Colonial Hotel
An indoor swimming pool with clear blue water, surrounded by brick walls and large windows.

2. Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
4.0 star property
Leominster
8.8 out of 10, Excellent, (1,006 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 Rp2.561.584
Rp2.861.290 total
includes taxes & fees
22 Nov - 23 Nov
Doubletree by Hilton Hotel Leominster
An indoor swimming pool with a mural of a beach scene, wooden beams, and a basketball court.

3. Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1,014 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 Rp2.893.844
Rp3.232.424 total
includes taxes & fees
29 Nov - 30 Nov
Great Wolf Lodge Boston / Fitchburg, MA
A large indoor swimming pool with lounge chairs and tables, ceiling fans, and a tiled floor.

4. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.2 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 Rp2.577.059
Rp2.796.109 total
includes taxes & fees
17 Nov - 18 Nov
Best Western Plus Keene Hotel
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.

5. 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, (1,002 reviews)
  • cleanliness
    Splash into comfort at this indoor pool oasis offering year-round aquatic escape in Keene.
The price is Rp2.421.398
Rp2.627.308 total
includes taxes & fees
16 Nov - 17 Nov
Keene Elm City Hotel, an Ascend Collection Hotel
An indoor swimming pool with a tiled edge, surrounded by lounge chairs and tables.

6. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (431 reviews)
  • cleanliness
    Splash into serenity at this inviting indoor pool hotel, where year-round swimming meets complete comfort and relaxation.
The price is Rp2.867.445
Rp3.111.178 total
includes taxes & fees
28 Nov - 29 Nov
Hampton Inn & Suites Keene
An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.

7. 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 Rp3.079.545
Rp3.341.306 total
includes taxes & fees
29 Nov - 30 Nov
Courtyard by Marriott Keene Downtown
A swimming pool surrounded by lush greenery and a white fence.

8. Howarth House B&B

Howarth House B&B
3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (126 reviews)
  • cleanliness
    Splash into bliss with private pools and outdoor hot tubs at this charming B&B retreat.
The price is Rp3.850.569
Rp3.850.569 total
includes taxes & fees
16 Nov - 17 Nov
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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Choose what matters most at hotels with a pool in Winchendon

Breakfast included
4 stars

Top Winchendon Hotel Reviews

An indoor swimming pool with a tiled edge, surrounded by lounge chairs and tables.
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene

10/10 Excellent

Great staff, great position. Stayed here whilst visiting friends in Keene. It was so easy to get around and close to Main Street.
United Kingdom
Neville
Reviewed October 3, 2025
Hampton Inn & Suites Keene

Frequently Asked Questions

What are some hotels with pools in Winchendon?

Great Wolf Lodge Boston / Fitchburg, MA: Features kitchens, a pool and Smart televisions. Motel 6 Leominster, MA: Offers 4 indoor swimming pools, a children's pool and free water park access. The Colonial Hotel: Offers a sauna, an indoor pool and free self parking. Doubletree by Hilton Hotel Leominster: Provides 2 restaurants, an indoor pool and free self parking. Keene Elm City Hotel, an Ascend Collection Hotel: 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 Hyde Park and V F W Park. 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.