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

Search Hotels with Pool 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 Pool

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Winchendon hotels with a pool

An indoor swimming pool with clear blue water, surrounded by brick walls and large windows.
A modern living room with two sofas, a coffee table, and a dining area with chairs and a table.
A bar area with a long counter, multiple bar stools, hanging pendant lights, and a bar stocked with bottles.
A gym with treadmills, a television, and weightlifting equipment.

1. 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.
฿5,358
฿5,985 total
includes taxes & fees
1 Nov - 2 Nov
Doubletree by Hilton Hotel Leominster
A pool area with lounge chairs and potted plants.
A formal dining room with round tables, dark wooden chairs, and white tablecloths.
A grand lobby with a staircase, a piano, comfortable seating, and large windows.
A brick building with a steeple, arched windows, and flags.

2. 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.
฿4,848
฿5,416 total
includes taxes & fees
1 Nov - 2 Nov
The Colonial Hotel
An indoor swimming pool with a tiled edge, surrounded by lounge chairs and a small table.
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.
A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.
A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

3. 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.
฿4,750
฿5,154 total
includes taxes & fees
1 Nov - 2 Nov
Best Western Plus Keene Hotel
An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.
A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.
A reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.
A gym with treadmills, elliptical machines, and stationary bikes.

4. 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.
฿4,724
฿5,125 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Keene
Waterslide
A group of people engaged in a craft activity at a table with various colored markers and papers.
Room
A rustic interior with wooden tables, a barrel, and a wall displaying colorful items.

5. 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.
฿6,276
฿7,010 total
includes taxes & fees
8 Oct - 9 Oct
Great Wolf Lodge Boston / Fitchburg, MA
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.
A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.
A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.
A modern bathroom with a glass-enclosed shower, a white toilet, and a towel rack with two towels.

6. 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.
฿4,008
฿4,349 total
includes taxes & fees
2 Nov - 3 Nov
Keene Elm City Hotel, an Ascend Collection Hotel
An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.
A multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".
A modern hotel lobby with a central bar area, multiple seating arrangements, and a reception desk.
A hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.

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.
฿6,367
฿6,908 total
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Keene Downtown
A swimming pool surrounded by lush greenery and a white fence.
A well-lit garden area with a gazebo, a small house, and a large tree in the background.
A bedroom with a fireplace, a bed, a chair, and a table with a lamp.
A white wooden pergola with a lattice design, surrounded by lush greenery and flowering plants.

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.
฿7,098
฿7,098 total
includes taxes & fees
7 Oct - 8 Oct
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

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

8/10 Good
"Hotel was great, except for a leak coming through the light over the tub coming from the room above. We were compensated with free breakfast and some points. The hotel staff was great, and I would stay at this hotel again."
Gary 1-night trip
Posted 19 hours ago
Doubletree by Hilton Hotel Leominster

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.

Explore a world of travel with Expedia