Short-Term Rentals in Skyline Country Club, MA: Compare 10+ Sites & Save

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  6.  Skyline Country Club

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158 Best Short-Term 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
Check Availability
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 Short-Term Rentals in Skyline Country Club.

Skyline Country Club Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 158 verified short-term rentals in Skyline Country Club, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Skyline Country Club vary depending on location, property size, and travel dates. Rates typically start from around $167 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Skyline Country Club include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Skyline Country Club, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Skyline Country Club often include amenities such as Fireplace/Heating, Child Friendly, and Wellness Facilities, providing a comfortable and convenient stay.

Short-term rentals in Skyline Country Club are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.