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
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Winchendon hotels with a pool

Indoor pool
Interior
Reception
Outdoor wedding area

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.
€147
includes taxes & fees
30 Aug - 31 Aug
The Colonial Hotel
Indoor pool
Bar (on property)
Presidential Suite, 1 King Bed, Non Smoking | Living area
Fitness facility

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.
€146
includes taxes & fees
27 Sept - 28 Sept
Doubletree by Hilton Hotel Leominster
Waterslide
Exterior
Children’s activities
Children’s activities

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.
€179
includes taxes & fees
30 Aug - 31 Aug
Great Wolf Lodge Boston / Fitchburg, MA
Pool
Lobby
Standard Room, 1 King Bed, Non Smoking
Fitness facility

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.
€131
includes taxes & fees
30 Aug - 31 Aug
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool
Lobby
Restaurant
Room

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.
€139
includes taxes & fees
30 Aug - 31 Aug
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.
€143
includes taxes & fees
8 Sept - 9 Sept
Hampton Inn & Suites Keene
Pool
Room
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.
€157
includes taxes & fees
6 Sept - 7 Sept
Courtyard by Marriott Keene Downtown
Outdoor pool
Interior
Front of property – evening/night
Garden

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.
€181
includes taxes & fees
31 Aug - 1 Sept
Howarth House B&B
Private kitchen
Interior
Private kitchen
Interior

9. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
€277
includes taxes & fees
30 Aug - 31 Aug
Modern Downtown Escape HotTub Fire Pit Games 12ppl
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"Has everything necessary for a two night stay."
Giovanna 2-night trip
Posted 1 hour ago
Keene Elm City Hotel, an Ascend Collection Hotel
Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

10/10 Excellent
"Breakfast was great and the servers were great."
Manuel 1-night trip
Posted 1 day ago
Doubletree by Hilton Hotel Leominster
The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"The property was excellent. Loved the pool and hot tub."
zavean 4-night trip
Posted 1 day ago
The Colonial Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"Clean room breakfast was good"
Lori 1-night trip
Posted 3 days ago
Best Western Plus Keene Hotel
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 4 days ago
Courtyard by Marriott Keene Downtown

Frequently asked questions

What are some hotels with pools in Winchendon?
Cozy Lakefront Cottage: Provides kitchens, a pool and Smart televisions. Modern Waterfront Gem w/ Dock on Lake Monomonac: Provides 4 indoor swimming pools, a children's pool and free water park access. Enjoy your stay in an antique home in an antique toy museum!: Features a sauna, an indoor pool and free self parking. Great Wolf Lodge Boston / Fitchburg, MA: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Colonial 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 Hyde 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.