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

Hotels with Swimming Pools in Winchendon

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Winchendon Hotels with Swimming Pools

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Winchendon hotels with a pool

1. The Colonial Hotel

The Colonial Hotel
Gardner
  • Dive into a serene indoor pool retreat with hot tub and sauna, perfect for year-round relaxation near Wachusett Mountain.
S$217
includes taxes & fees
30 Aug - 31 Aug
The Colonial Hotel

2. Doubletree by Hilton Hotel Leominster

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.
S$225
includes taxes & fees
6 Sept - 7 Sept
Doubletree by Hilton Hotel Leominster

3. Great Wolf Lodge Boston / Fitchburg, MA

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.
S$259
includes taxes & fees
30 Aug - 31 Aug
Great Wolf Lodge Boston / Fitchburg, MA

4. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
  • Splash into comfort at this indoor pool oasis offering year-round aquatic escape in Keene.
S$185
includes taxes & fees
8 Sept - 9 Sept
Keene Elm City Hotel, an Ascend Collection Hotel

5. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
  • Splash into luxury at this hotel's sparkling indoor pool, complete with plush sun loungers and serene atmosphere.
S$205
includes taxes & fees
27 Aug - 28 Aug
Best Western Plus Keene Hotel

6. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
  • Splash into serenity at this inviting indoor pool hotel, where year-round swimming meets complete comfort and relaxation.
S$208
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn & Suites Keene

7. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
Keene
  • Dive into the year-round aquatic escape at this art deco hotel with a pristine indoor pool.
S$233
includes taxes & fees
6 Sept - 7 Sept
Courtyard by Marriott Keene Downtown

8. Howarth House B&B

Howarth House B&B
Fitchburg
  • Splash into bliss with private pools and outdoor hot tubs at this charming B&B retreat.
S$268
includes taxes & fees
31 Aug - 1 Sept
Howarth House B&B
View all properties

Choose what matters most at hotels with a pool in Winchendon

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Winchendon Hotel Reviews

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"Clean room breakfast was good"
Lori 1-night trip
Posted 11 hours ago
Best Western Plus Keene Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"It was good!"
Ingrid 4-night trip
Posted 1 day ago
Keene Elm City Hotel, an Ascend Collection Hotel
Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

10/10 Excellent
"Very good."
Regieta 4-night trip
Posted 2 days ago
Doubletree by Hilton Hotel Leominster
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"Everything was great!! Beds were super comfortable."
Karen 1-night trip
Posted 2 days ago
Courtyard by Marriott Keene Downtown

Frequently asked questions

What are some hotels with pools in Winchendon?
Great Wolf Lodge Boston / Fitchburg, MA: Features kitchens, a pool and Smart televisions. The Colonial Hotel: Resort steps from Great Wolf Lodge Waterpark. Provides 4 indoor swimming pools, a children's pool and free water park access. Keene Elm City Hotel, an Ascend Collection Hotel: Features a sauna, an indoor pool and free self parking. Days Inn by Wyndham Keene NH: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. Best Western Plus Keene 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.

Explore a world of travel with Expedia