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Hotels with Swimming Pool in Winchendon, Massachusetts

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Check availability on Winchendon Hotels with Swimming Pool

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

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 gym with treadmills, a television, and weightlifting equipment.
A bar area with a long counter, multiple bar stools, hanging pendant lights, and a bar stocked with bottles.

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.
P9,965
P11,131 total
includes taxes & fees
Nov 1 - Nov 2
Doubletree by Hilton Hotel Leominster
A pool area with lounge chairs and potted plants.
A grand lobby with a staircase, a piano, comfortable seating, and large windows.
A brick building with a steeple, arched windows, and flags.
A formal dining room with round tables, dark wooden chairs, and white tablecloths.

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.
P9,017
P10,073 total
includes taxes & fees
Nov 1 - Nov 2
The Colonial Hotel
An indoor swimming pool with a tiled edge, surrounded by lounge chairs and a small table.
A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.
A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

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.
P8,867
P9,620 total
includes taxes & fees
Nov 1 - Nov 2
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 gym with treadmills, elliptical machines, and stationary bikes.
A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.

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.
P8,785
P9,532 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Keene
Waterslide
A hotel with a prominent sign reading "Great Wolf Lodge."
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.
P11,697
P13,066 total
includes taxes & fees
Oct 7 - Oct 8
Great Wolf Lodge Boston / Fitchburg, MA
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.
A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.
A hotel room with a bed, a desk, a chair, a wooden door, and a window.
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.
P7,454
P8,088 total
includes taxes & fees
Nov 2 - Nov 3
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 hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.
A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.
A modern hotel lobby with a central bar area, multiple seating arrangements, and a reception desk.

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.
P11,825
P12,831 total
includes taxes & fees
Oct 28 - Oct 29
Courtyard by Marriott Keene Downtown
A swimming pool surrounded by lush greenery and a white fence.
A spacious living room with two patterned sofas, a coffee table, and a fireplace.
A white wooden pergola with a lattice design, surrounded by lush greenery and flowering plants.
A bedroom with a fireplace, a bed, a chair, and a table with a lamp.

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.
P13,230
P13,230 total
includes taxes & fees
Oct 7 - Oct 8
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 16 hours ago
Doubletree by Hilton Hotel Leominster
Motel 6 Leominster, MA

Motel 6 Leominster, MA

8/10 Good
"This motel was a lot better than I thought. The only thing I didn’t like were the mattresses. They were too soft. But the location was great. There were so many places to eat."
Juan 3-night trip
Posted 2 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. Motel 6 Leominster, MA: Offers 4 indoor 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 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, 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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