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

Winchendon Hotel Guide - Hotels with Pool in Winchendon, Massachusetts

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Check availability on Winchendon Hotels with Pool

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Winchendon hotels with a pool

A pool area with lounge chairs and potted plants.
A wooden pergola structure in a garden setting with a paved walkway leading to it.
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.

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.
€144
includes taxes & fees
1 Nov - 2 Nov
The Colonial Hotel
An indoor swimming pool with clear blue water, surrounded by brick walls and large windows.
A small, enclosed shower area with a white tiled wall, a handheld showerhead, a small shelf, and a white seat.
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.

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.
€159
includes taxes & fees
1 Nov - 2 Nov
Doubletree by Hilton Hotel Leominster
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.

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.
€186
includes taxes & fees
14 Oct - 15 Oct
Great Wolf Lodge Boston / Fitchburg, MA
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.
A modern bathroom with a glass-enclosed shower, a white toilet, and a towel rack with two towels.
A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.
A hotel room with a bed, a desk, a chair, a wooden door, and a window.

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.
€115
includes taxes & fees
2 Nov - 3 Nov
Keene Elm City Hotel, an Ascend Collection Hotel
An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.
A reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.
A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.
A gym with treadmills, elliptical machines, and stationary bikes.

5. 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.
€150
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn & Suites Keene
An indoor swimming pool with a tiled edge, surrounded by lounge chairs and a small table.
A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.
A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.

6. 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.
€137
includes taxes & fees
1 Nov - 2 Nov
Best Western Plus Keene Hotel
A swimming pool surrounded by lush greenery and a white fence.
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.
A spacious living room with two patterned sofas, a coffee table, and a fireplace.

7. 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.
€189
includes taxes & fees
18 Oct - 19 Oct
Howarth House B&B
An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.
A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.
A hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.
A modern hotel lobby with a central bar area, multiple seating arrangements, and a reception desk.

8. 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.
€183
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Keene Downtown
A modern kitchen with a wooden countertop, dark cabinets, and a large window.
A modern kitchen with a wooden table and benches, a brick column, and a view of the living area.
A home interior with a wooden staircase, a desk with a chair, a refrigerator, and a lamp.
A modern kitchen with a wooden island, blue cabinets, and a brick wall.

9. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
€327
includes taxes & fees
20 Oct - 21 Oct
Modern Downtown Escape HotTub Fire Pit Games 12ppl
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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
"This resort was amazing"
Abderaouf 1-night trip
Posted 4 hours 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
"This is a great place to stay in Keene! The location is perfect, the room was immaculate, and the breakfast was great!"
Mary 1-night trip
Posted 9 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"The hotel needs some updating, and could be a little cleaner. Bathroom door looked like it had not been cleaned in a long time. The staff was friendly, and breakfast was good."
Teresa D 1-night trip
Posted 1 day ago
Best Western Plus Keene Hotel
Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

10/10 Excellent
"."
John 3-night trip
Posted 3 days ago
Doubletree by Hilton Hotel Leominster

Frequently asked questions

What are some hotels with pools in Winchendon?
Modern Waterfront Gem w/ Dock on Lake Monomonac: Features kitchens, a pool and Smart televisions. Cozy Lakefront Cottage: Offers 4 indoor swimming pools, a children's pool and free water park access. Great Wolf Lodge Boston / Fitchburg, MA: Offers a sauna, an indoor pool and free self parking. Motel 6 Leominster, MA: Provides 2 restaurants, an indoor pool and free self parking. The Colonial 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.