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

Hotels with Swimming Pool in Winchendon, Massachusetts

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Check availability on Winchendon Hotels with Swimming Pool

Tonight
Aug 21 - Aug 22
Tomorrow
Aug 22 - Aug 23
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Winchendon hotels with a pool

Indoor pool
Outdoor wedding area
Reception
Front of property

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.
P9,431
P10,534 total
includes taxes & fees
Aug 23 - Aug 24
The Colonial Hotel
Waterslide
Exterior
Children's activities
Room

2. 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.
P11,283
P12,604 total
includes taxes & fees
Aug 24 - Aug 25
Great Wolf Lodge Boston / Fitchburg, MA
Pool
Lobby
Fitness facility
Room

3. 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.
P7,399
P8,028 total
includes taxes & fees
Sep 1 - Sep 2
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool
Living area
Bar (on property)
Bathroom shower

4. 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.
P9,809
P10,956 total
includes taxes & fees
Aug 30 - Aug 31
Doubletree by Hilton Hotel Leominster
Indoor pool
Room
Lobby
Property amenity

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.
P9,187
P9,968 total
includes taxes & fees
Aug 23 - Aug 24
Best Western Plus Keene Hotel
Pool
Fitness facility
Breakfast area
Reception

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.
P9,303
P10,094 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Keene
Pool
Breakfast meal
Bar (on property)
Exterior

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.
P11,071
P12,012 total
includes taxes & fees
Aug 30 - Aug 31
Courtyard by Marriott Keene Downtown
Outdoor pool
Room
Garden
Interior

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.
P13,041
P13,041 total
includes taxes & fees
Aug 23 - Aug 24
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

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent
"Always a good time!"
Renae 3-night trip
Posted 1 hour ago
Great Wolf Lodge Boston / Fitchburg, MA
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Staff was great. Room was fine. Besides the small bathroom set up and basic continental breakfast, stay was great."
Krystal 1-night trip
Posted 2 days ago
Keene Elm City Hotel, an Ascend Collection Hotel
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"Comfortable, clean room. Helpful and friendly staff. Convenient location."
Deborah 3-night trip
Posted 2 days ago
Courtyard by Marriott Keene Downtown
Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"Fantastic stay"
Megan 6-night trip
Posted 3 days ago
Motel 6 Leominster, MA

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. Provides 4 indoor 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 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, 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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