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

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Check availability on Winchendon Hotels with a Pool

Tonight
Aug 24 - Aug 25
Tomorrow
Aug 25 - Aug 26
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Winchendon hotels with a pool

Indoor pool
Interior
Front of property
Reception

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.
￥24,311
￥27,156 total
includes taxes & fees
Aug 26 - Aug 27
The Colonial Hotel
Indoor pool
Lobby
In-room safe, desk, iron/ironing board, cribs (free)
Standard Room, 1 King Bed, Non Smoking | In-room safe, desk, iron/ironing board, cribs (free)

2. 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.
￥19,074
￥20,695 total
includes taxes & fees
Sep 1 - Sep 2
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers
Pub
Fitness facility
Room, 1 King Bed, Accessible, Non Smoking (Roll-in Shower) | Bathroom shower

3. 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.
￥25,286
￥28,244 total
includes taxes & fees
Sep 6 - Sep 7
Doubletree by Hilton Hotel Leominster
Waterslide
Deluxe Queen Suite | In-room safe, iron/ironing board, alarm clocks, bed sheets
Children's activities
Children's activities

4. 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.
￥29,088
￥32,491 total
includes taxes & fees
Aug 25 - Aug 26
Great Wolf Lodge Boston / Fitchburg, MA
Indoor pool, open 6:00 AM to 10:00 PM, sun loungers
Property amenity
Premium bedding, desk, laptop workspace, blackout drapes
Lobby

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.
￥23,684
￥25,698 total
includes taxes & fees
Aug 25 - Aug 26
Best Western Plus Keene Hotel
Indoor pool
Exterior
Free daily buffet breakfast
Fitness facility

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.
￥23,982
￥26,021 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Keene
Outdoor pool
Garden
North Superior Room, 1 Queen Bed, Garden View | Premium bedding, laptop workspace, iron/ironing board, WiFi (free)
Front of property - evening/night

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.
￥33,618
￥33,618 total
includes taxes & fees
Aug 25 - Aug 26
Howarth House B&B
Indoor pool
Pub
Daily cooked-to-order breakfast for a fee
Exterior

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.
￥28,539
￥30,965 total
includes taxes & fees
Aug 30 - Aug 31
Courtyard by Marriott Keene Downtown
Coffee/tea maker, fridge, microwave, oven
Interior
Outdoor spa tub
Interior

9. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
￥26,886
￥53,145 total
includes taxes & fees
Aug 25 - Aug 26
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
"The room was clean and stocked with the amenities expected, including a fridge and a microwave. Staff was very helpful and kind on check in. Breakfast was a standard continental. Not the best food but there was an array of options."
Samantha 1-night trip
Posted less than an hour ago
Keene Elm City Hotel, an Ascend Collection Hotel
Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

10/10 Excellent
"Staff was amazing from the moment we walked in the door. They were having an issue with the key entry and staff had to escort all guests to their rooms. Let me just say they handled like champs and never missed a beat with their professionalism."
Renee 1-night trip
Posted 19 hours ago
Doubletree by Hilton Hotel Leominster
Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"Staff is always accomadating"
PAUL 1-night trip
Posted 2 days ago
Motel 6 Leominster, MA

Frequently asked questions

What are some hotels with pools in Winchendon?
Cozy Lakefront Cottage: Features kitchens, a pool, and Smart TVs. Enjoy your stay in an antique home in an antique toy museum!: Resort steps from Great Wolf Lodge Waterpark. Provides 4 indoor pools, a children's pool, and free water-park access. Great Wolf Lodge Boston / Fitchburg, MA: Features a sauna, an indoor pool, and free self parking. The Colonial Hotel: Offers buffet, an indoor pool, and complimentary wired internet access. Keene Elm City Hotel, an Ascend Collection 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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