Vacation Rentals in Skyline Country Club, MA: Compare 10+ Sites & Save

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  4.  Massachusetts

  5.  Lanesborough
  6.  Skyline Country Club

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130 Best Vacation Rentals in Skyline Country Club (Starting from $167)

Lakeside Berkshires Home Near Hiking and Skiing!
Lakeside Berkshires Home Near Hiking and Skiing!
House
Lanesborough, MA, USA
0.7k from Skyline Country Club center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms7 Guests
New to Booking
$471
Average price / night
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Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
House
Lanesborough, MA, 01237, United States
0.5k from Skyline Country Club center

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

4 Bedrooms7 Guests
9.8

Exceptional

13 reviews

$465
Average price / night
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Lake Views and Dock Access - Pittsfield Cottage!
Lake Views and Dock Access - Pittsfield Cottage!
House
Pittsfield, MA, USA
1.6k from Skyline Country Club center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms6 Guests
New to Booking
$552
Average price / night
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Lakeside Berkshires Home Near Hiking & Skiing!
Lakeside Berkshires Home Near Hiking & Skiing!
House
Lanesborough, MA, 01237, United States
0.7k from Skyline Country Club center

Balcony, Crib, Dryer, Extra Bed, Free Parking, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms7 Guests
8.8

Fabulous

5 reviews

$500
Average price / night
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Pittsfield Home with Deck - 12 Mi to Jiminy Peak!
Pittsfield Home with Deck - 12 Mi to Jiminy Peak!
House
Pittsfield, MA, USA
4.5k from Skyline Country Club center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Ski resorts

3 Bedrooms10 Guests
9.0

Fabulous

1 reviews

$370
Average price / night
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Lakefront Home on Pontoosuc Lake, the Berkshires
Lakefront Home on Pontoosuc Lake, the Berkshires
House
Lanesborough, MA, 01237, United States
0.8k from Skyline Country Club center

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

3 Bedrooms8 Guests
9.2

Superb

5 reviews

$476
Average price / night
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Family-Friendly Hancock Home Walk to Slopes!
Family-Friendly Hancock Home Walk to Slopes!
House
Hancock, MA, USA
6.9k from Skyline Country Club center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

4 Bedrooms15 Guests
New to Booking
$1320
Average price / night
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Ray of Sunshine Berkshire Home on Pontoosuc Lake
Ray of Sunshine Berkshire Home on Pontoosuc Lake
House
Pittsfield, MA, 01201, United States
1.5k from Skyline Country Club center

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

5 Bedrooms14 Guests
10.0

Exceptional

15 reviews

$851
Average price / night
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Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort
Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort
House
Hancock, MA, USA
6.9k from Skyline Country Club center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms10 Guests
8.5

Very Good

10 reviews

$618
Average price / night
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Escape to your cozy retreat near Pontoosuc Lake and Jiminy Peak
Escape to your cozy retreat near Pontoosuc Lake and Jiminy Peak
House
Pittsfield, MA, 01201, United States
1.5k from Skyline Country Club center

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

2 Bedrooms4 Guests
10.0

Exceptional

34 reviews

$339
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
7.1k from Skyline Country Club 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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Lake Views & Dock Access - Pittsfield Cottage!
Lake Views & Dock Access - Pittsfield Cottage!
Cottage
Pittsfield, MA, 01201, United States
1.6k from Skyline Country Club center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Living Area

4 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$497
Average price / night
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Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Apartment
Hancock, MA, USA
7.1k from Skyline Country Club center

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

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$279
Average price / night
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Lake View Cozy Cottage
Lake View Cozy Cottage
House
Pittsfield, MA, 01201, United States
1.6k from Skyline Country Club center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
New to Booking
$404
Average price / night
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half Mi to Jiminy Peak Condo with Pool and Hot Tub
half Mi to Jiminy Peak Condo with Pool and Hot Tub
Apartment
Hancock, MA, USA
7.1k from Skyline Country Club center

Apartments, Accommodations, Parking, Lodgings, Hot tubs, Places to stay, Ski resorts, Condos

2 Bedrooms4 Guests
New to Booking
$331
Average price / night
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A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Cabin
Pittsfield, MA, 01201, United States
1.7k from Skyline Country Club center

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

2 Bedrooms5 Guests
10.0

Exceptional

129 reviews

$307
Average price / night
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Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Apartment
Hancock, MA, USA
7.1k from Skyline Country Club center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Condos

1 Bedroom4 Guests
7.5

Good

2 reviews

$167
Average price / night
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Hearts Desire is your private escape.
Hearts Desire is your private escape.
House
Lanesborough, MA, 01237, United States
1.9k from Skyline Country Club center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
10.0

Exceptional

105 reviews

$281
Average price / night
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Elegant Pittsfield Home Near Downtown and Skiing!
Elegant Pittsfield Home Near Downtown and Skiing!
House
Pittsfield, MA, USA
7.1k from Skyline Country Club center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

5 Bedrooms10 Guests
9.7

Exceptional

3 reviews

$947
Average price / night
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3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
House
Pittsfield, MA, 01201, United States
2.0k from Skyline Country Club center

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

3 Bedrooms6 Guests
7.8

Good

7 reviews

$493
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
7.1k from Skyline Country Club 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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Berkshire Lake Beauty-Modern Amenities On The Lake
Berkshire Lake Beauty-Modern Amenities On The Lake
House
Pittsfield, MA, 01201, United States
2.0k from Skyline Country Club center

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

5 Bedrooms14 Guests
10.0

Exceptional

112 reviews

$595
Average price / night
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Cozy Cottage in Berkshires: Minutes to Jiminy Peak
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
House
Lanesborough, MA, 01237, United States
2.1k from Skyline Country Club center

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

4 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$381
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
2.4k from Skyline Country Club 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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Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
House
Pittsfield, MA, 01201, United States
2.5k from Skyline Country Club center

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

5 Bedrooms14 Guests
10.0

Exceptional

48 reviews

$1131
Average price / night
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Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
House
Pittsfield, MA, 01201, United States
2.5k from Skyline Country Club center

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

4 Bedrooms10 Guests
10.0

Exceptional

64 reviews

$700
Average price / night
Check Availability
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
House
Lanesborough, MA, 01237, United States
2.7k from Skyline Country Club center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, Outdoor Space

1 Bedroom2 Guests
9.8

Exceptional

277 reviews

$206
Average price / night
Check Availability

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 in Skyline Country Club.

Skyline Country Club Vacation Rentals on the Map

Frequently Asked Questions

You can explore 130 verified vacation rentals in Skyline Country Club. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Skyline Country Club vary depending on the season, property size, and location. Rates typically start from around $167 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Skyline Country Club include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Skyline Country Club welcome pets. Currently, 20 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Skyline Country Club often include amenities such as Fireplace/Heating, Child Friendly, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.