Vacation Rentals with Private Pool in Hancock, MA: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Massachusetts

  5.  Hancock

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18 Best Vacation Rentals with Private Pool in Hancock (Starting from $225)

Mountain View Suite on Jiminy Peak Ski On Off -New
Mountain View Suite on Jiminy Peak Ski On Off -New
Apartment
Hancock, MA, USA
1.1k from Hancock center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Ski resorts

1 Bedroom4 Guests
9.4

Superb

19 reviews

$335
Average price / night
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Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere
Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere
Apartment
Hancock, MA, 01237, United States
1.1k from Hancock center

AC, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$231
Average price / night
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1st Floor Mountain View Suite Ski On Off At Jiminy- Fully Redone Decor
1st Floor Mountain View Suite Ski On Off At Jiminy- Fully Redone Decor
Apartment
Hancock, MA, USA
1.1k from Hancock center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Ski resorts

1 Bedroom4 Guests
7.7

Good

6 reviews

$335
Average price / night
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Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Apartment
Hancock, MA, 01237, United States
1.1k from Hancock center

AC, Elevator, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

1 Bedroom4 Guests
9.8

Exceptional

25 reviews

$231
Average price / night
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Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor
Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor
Apartment
Hancock, MA, USA
1.1k from Hancock center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$335
Average price / night
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Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Apartment
Hancock, MA, 01237, United States
1.1k from Hancock center

AC, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom4 Guests
10.0

Exceptional

3 reviews

$231
Average price / night
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Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4
Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4
Apartment
Hancock, MA, USA
1.1k from Hancock center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom4 Guests
9.2

Superb

18 reviews

$226
Average price / night
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Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Apartment
Hancock, MA, 01237, United States
1.2k from Hancock center

AC, Extra Bed, Fitness Equipment, Heater, Hot Tub, Internet, Kitchen, Microwave, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

5 reviews

$231
Average price / night
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Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak
Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak
Apartment
Hancock, MA, USA
1.1k from Hancock center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Ski resorts

1 Bedroom4 Guests
7.7

Good

10 reviews

$279
Average price / night
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Woodland 5-BR Retreat 5-Min to Jiminy Peak
Woodland 5-BR Retreat 5-Min to Jiminy Peak
House
Hancock, MA, 01237, United States
3.1k from Hancock center

Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

5 Bedrooms10 Guests
10.0

Exceptional

14 reviews

$521
Average price / night
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Gorgeous 1st FL Mtn View Jiminy Suite Sleeps 4 Ski On Off
Gorgeous 1st FL Mtn View Jiminy Suite Sleeps 4 Ski On Off
Apartment
Hancock, MA, USA
1.1k from Hancock center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Ski resorts

1 Bedroom4 Guests
8.9

Fabulous

14 reviews

$335
Average price / night
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Mountain Blossom Retreat by Evergreen Home
Mountain Blossom Retreat by Evergreen Home
House
Lanesborough, MA, 01237, United States
4.6k from Hancock center

AC, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

3 Bedrooms8 Guests
10.0

Exceptional

10 reviews

$879
Average price / night
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Jurassic Dino Suite Jiminy-Must See Sleeps 4
Jurassic Dino Suite Jiminy-Must See Sleeps 4
Apartment
Hancock, MA, USA
1.2k from Hancock center

Apartments, Cheap, Accommodations, Pools, Lodgings, Vacation rentals, Places to stay, Family, Ski resorts

1 Bedroom4 Guests
9.0

Fabulous

4 reviews

$335
Average price / night
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Sleeps 40 • Heated Pool • Hot Tub • Game Room | Brookside Mountain Retreat
Sleeps 40 • Heated Pool • Hot Tub • Game Room | Brookside Mountain Retreat
House
Stephentown, NY, 12168, United States
5.5k from Hancock center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

13 Bedrooms40 Guests
New to Booking
$2363
Average price / night
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Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury
Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury
Apartment
Hancock, Massachusetts, USA
1.3k from Hancock center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals

2 Bedrooms8 Guests
9.0

Fabulous

26 reviews

$251
Average price / night
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Lakeside Home With Pool-Completely Renovated
Lakeside Home With Pool-Completely Renovated
House
Pittsfield, MA, 01201, United States
6.5k from Hancock center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

6 Bedrooms16 Guests
10.0

Exceptional

37 reviews

$642
Average price / night
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Vacation Village in the Berkshires
Vacation Village in the Berkshires
Resort
Hancock, Massachusetts, USA
2.0k from Hancock center

Luxury, Accommodations, Pools, Resorts, Parking, Golf, Romantic, 5-star, Lodgings

482 Bedrooms44 Guests
8.6

Fabulous

1472 reviews

$225
Average price / night
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Sweeping Mountain Views in the Berkshires
Sweeping Mountain Views in the Berkshires
House
New Lebanon, NY, 12125, United States
9.0k from Hancock center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

4 Bedrooms12 Guests
9.6

Exceptional

7 reviews

$1000
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Private Pool in Hancock.

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Hancock Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 18 verified vacation rentals with a private pool in Hancock. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Hancock vary depending on the property size, location, and travel season. Rates typically start from around $225 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Hancock also welcome pets. Currently, 3 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Hancock often include additional features such as Fireplace/Heating, Pool, and Private Pool. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Hancock include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.