40+ Vacation Rentals Near Skyline Trail |
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Rentthecottages - Vacation Rentals in Skyline Trail

Property Image From US $251
         

10.0 (58 Reviews)
House
Berkshire Lake access
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From US $457
         

10.0 (19 Reviews)
House
Beautiful Timber Frame Home in the Berkshires /Available for Long Term
  • Air Conditioner
  • Parking
  • TV

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Property Image From US $830
         

10.0 (5 Reviews)
House
1840's Whaling Captain's Farm Estate, 6-10 guests
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From US $352
         

10.0 (5 Reviews)
House
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.
  • Parking
  • TV
  • View

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Property Image From US $271
         

10.0 (1 Review)
Cottage
Private Lake Cottage on 3 acres w/350 sq. ft. deckn
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

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Property Image From US $281
         

9.8 (80 Reviews)
House
Bershire Home Rental: Enjoy Berkshire Fall Foliage
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From US $191
         

9.8 (19 Reviews)
House
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
  • Air Conditioner
  • Parking
  • TV

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Property Image From US $582
         

9.6 (9 Reviews)
House
Wildlife Retreat in the Forest
  • Parking
  • TV
  • Balcony/Terrace

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Property Image From US $1,718
         

New
House
The Pease-Hastings HousenCharming 7-bedroom Victorian home in lovely Worthington
  • Parking
  • TV
  • Balcony/Terrace

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Property Image From US $559
         

New
Cabin
Cozy Modern 4 Bedroom Log Cabin on 45 Secluded Acres in the Berkshires
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities

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Property Image From US $339
         

New
House
Beautiful Renovated Home, Close to Multiple Ski Mountains.
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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Property Image From US $240
         

New
House
Historic 1804 house in N Becket Village in the Berkshires
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens

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Property Image From US $440
         

9.8 (56 Reviews)
House
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From US $264
         

10.0 (176 Reviews)
House
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
  • Parking
  • Pet Friendly
  • TV

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Property Image From US $212
         

10.0 (89 Reviews)
House
Remote and Relaxing Cabin in the Berkshires
  • Parking
  • Balcony/Terrace
  • Security/Safety

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Property Image From US $177
         

10.0 (20 Reviews)
Apartment
Ashmere Lakefront Apartment
  • Air Conditioner
  • Parking
  • TV

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Property Image From US $426
         

10.0 (2 Reviews)
House
Quintessential 1860's Berkshire farmhouse with mountain views on 30 acres.
  • Parking
  • Pet Friendly
  • TV

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Property Image From US $138
         

9.8 (203 Reviews)
Cabin
A-Frame in Sherwood Forest
  • Parking
  • Pet Friendly
  • TV

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Property Image From US $355
         

8.6 (4 Reviews)
House
New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond
  • Balcony/Terrace
  • Security/Safety
  • Fireplace/Heating

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Property Image From US $185
         

New
Cabin
The Perfect Escape; Log Cabin situated on 40 Secluded Acres of Wilderness
  • Air Conditioner
  • Parking
  • Pool

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Property Image From US $180
         

New
House
In the forest, 1-bedroom home, floor to ceiling windows in peaceful Becket
  • Parking
  • Security/Safety
  • Bedding/Linens

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Property Image From US $224
         

9.4 (70 Reviews)
Other
Charming Farmhouse - quiet, private & peaceful
  • Air Conditioner
  • Parking
  • TV

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Property Image From US $220
         

10.0 (23 Reviews)
Other
A simple kind of paradise
  • Parking
  • Pool
  • TV

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Property Image From US $180
         

New
Cottage
Berkshire Cottage on Ashmere Lake
  • Child Friendly

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★ Pro Tip: Rentthecottages makes it easy to compare the best listings on Rentthecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Rentthecottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Skyline Trail.

Weather in Skyline Trail

View the weather forecast for Skyline Trail before booking your Skyline Trail Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Skyline Trail, MA

Rentthecottages offers a large selection of top attractions around Skyline Trail. Research things to do on your vacation before you visit Skyline Trail.


Lee Prime Outlets Cranwell Golf Club Jacob's Pillow Otis Ridge October Mountain State Forest Beartown State Forest Chester Town Hall Chesterfield Gorge Lee Library Goose Pond Reservation Canoe Meadows Wildlife Sanctuary Kushi Institute Becket Land Trust Historic Quarry Crane Museum of Papermaking Herman Melville's Arrowhead Berkshire Mountain Country Store Guido's Marketplace Glendale Falls Wood's Pond Wahconah Falls State Park