Hancock Hotel Guide - Hotels with Pool in Hancock, Massachusetts

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Check availability on Hancock Hotels with Pool

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Hancock hotels with a pool

Indoor pool, outdoor pool
UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
The price is €340
includes taxes & fees
24 Jan - 25 Jan 2026
UNIQUE - 1BR Country Condo @ Jiminy Peak
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is €208
includes taxes & fees
4 Jan - 5 Jan 2026
Jiminy Peak Mountain Resort
Pool
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
8.0 out of 10, Very good, (8)
"Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. "
United States
PK N.
The price is €292
includes taxes & fees
5 Jan - 6 Jan 2026
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is €263
includes taxes & fees
6 Jan - 7 Jan 2026
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Exterior
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Hancock
10.0 out of 10, Exceptional, (1)
The price is €264
includes taxes & fees
5 Jan - 6 Jan 2026
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Indoor pool
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock
9.8 out of 10, Exceptional, (18)
"We enjoyed our stay in this adorable Disney Themed condo. The attention to detail in the theming was fantastic and the condo was perfect for our February Vacation ski trip."
United States
Allison V.
The price is €366
includes taxes & fees
29 Dec - 30 Dec
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Indoor pool
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is €264
includes taxes & fees
8 Jan - 9 Jan 2026
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Exterior
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (30)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is €344
includes taxes & fees
25 Jan - 26 Jan 2026
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6)
"Great location. Very nice vacation. Would def go again. "
United States
Elizabeth M.
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Exterior
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
Hancock
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hancock Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The bed was very comfortable. The staff was helpful and courteous"
Timothy 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

What's it like visiting Hancock?
If lounging by a pool is your idea of the perfect getaway, you might want to think about family-friendly Hancock, which has 19 places to stay with pools. During your visit, you can explore attractions such as Jiminy Peak Mountain Resort and Alpine Super Slide, and then relax poolside at one of the accommodation options in Hancock that guests like for their pools.
What are some accommodation options with pools in Hancock?
Jiminy Peak Mountain Resort: Condo resort, 1-minute walk from Jiminy Peak Mountain Resort. Features 2 restaurants, an outdoor pool and 2 bars. Club Wyndham Bentley Brook: Hotel, 1-minute walk from Jiminy Peak Mountain Resort. Offers an indoor pool, an outdoor pool and a sauna. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants: Resort steps from Jiminy Peak Mountain Resort. Provides complimentary wireless Internet access, a pool and kitchens. Comfortable Berkshires retreat on mtn resort, SISO: Holiday home, 11-minute walk from Jiminy Peak Mountain Resort. Features a sauna, a communal pool and complimentary wireless Internet access. Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool and free self parking.
How many hotels with pools will I be able to find in Hancock?
Expedia's 19 hotels in Hancock give you a great choice for your poolside getaway.
What is there to see and do in Hancock?
Make a point to visit attractions such as Alpine Super Slide and Mountain Coaster. Discover sights such as Jiminy Peak Mountain Resort during your stay. The mountain views, skiing and hiking are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Hancock?
Taking the local weather in Hancock into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Hancock are January, March, February and November, with each month seeing an average of 18 cm of snowfall.