Top Winter Vacations - Vacation Rentals in Housatonic

Tranquil 3 BR Stockbridge House w/Private Deck! From US $320
         

10.0 (92 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Granville House From US $225
         

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9.9 (137 Reviews)
Bed & Breakfast
  • Air Conditioner
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  • Pet Friendly
Granville House From US $335
         

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10.0 (88 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Stockbridge Home, Come Experience The Berkshires! From US $387
         

10.0 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Secluded Family Home in Serene Stockbridge Woods From US $454
         

10.0 (23 Reviews)
House
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  • Parking
  • Pet Friendly
Classic Stockbridge Cottage From US $433
         

10.0 (17 Reviews)
House
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  • Parking
  • Pet Friendly

Luxury Places to Stay in Housatonic

Over 96+ Luxury Places to Stay in or Near Housatonic
Luxuriously Comfortable Country Home From US $1,206
         

Fully renovated sprawling farmhouse in Great Barrington From US $1,005
         

8.0 (1 Review)
House
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  • Pet Friendly
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Idyllic Retreat; Hot Tub/Sauna by Evergreen Home From US $800
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Housatonic

Over 13+ Top-Rated Vacation Rentals with a Pool in or Near Housatonic
Fabulous Apartment - Great Barrington From US $248
         

10.0 (3 Reviews)
Apartment
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  • Pool
Stockbridge Country Inn From US $314
         

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9.3 (16 Reviews)
Bed & Breakfast
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  • Pool
Poolside Luxe at Long Pond From US $459
         

9.0 (2 Reviews)
House
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  • Parking
  • Pet Friendly
The Little Lion From US $144
         

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8.6 (547 Reviews)
Hotel
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  • Parking
  • Pool
Modern Cottage Minutes from Downtown Great Barrington From US $713
         

Pet-Friendly Vacation Rentals in Housatonic

Over 37+ Pet-Friendly Vacation Rentals in or Near Housatonic
1 Mi to Dtwn: Cottage w/Large Yard in Stockbridge From US $443
         

10.0 (4 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Beautiful House in the Woods: Huge Yard, Hot Tub From US $516
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Outdoor Sauna, Hot tub, Fire Pit, Dogs Welcome! From US $486
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
8 Mi to Tanglewood & Butternut Ski: Spacious Home! From US $440
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sweet Cozy Victorian in Housatonic. Close to everything. From US $186
         

Lofted Hideaway on Pixley Hill From US $333
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming Winter Ski Rental in Great Barrington, MA From US $252
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Housatonic

Over 20+ Large Vacation Homes & Villas in or Near Housatonic
Great Barrington Lakeside Getaway w/Kayak & Grill From US $384
         

Too Good AKA 2 Goodrich St From US $499
         

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10.0 (1 Review)
House
  • Air Conditioner
  • View
  • Security/Safety
Autumn Family Getaway From US $431
         

9.8 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Spacious & Serene Berkshires Retreat In The Woods From US $581
         

8.4 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Housatonic

Over 1+ Wheelchair Accessible Vacation Homes in or Near Housatonic
The Little Lion From US $175
         

7.2 (218 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Housatonic Varoom and Airbnb Places to Stay Under $200

Over 6+ Housatonic Varoom and Airbnb Places to Stay Under $200
Morgan's Millhouse (Front) From US $99
         

9.8 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Entire home hosted by Morgan From US $125
         

9.6 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
10 Minutes to Ski Butternut! Dogs Welcome! From US $100
         

New
Other
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  • Bedding/Linens
  • Wellness Facilities

Instantly Bookable Vacation Homes in Housatonic

Over 17+ Instantly Bookable Vacation Homes in or Near Housatonic
Spacious & Modern Berkshires Getaway From US $492
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Stay Lakeside This Summer! From US $324
         

9.8 (80 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Greek Revival Farmhouse in Stockbridge From US $397
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Loft Style Cabin In West Stockbridge, Book Now! From US $404
         

About Housatonic Vacation Rentals

With more than 105 Housatonic vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Topwintervacations and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Housatonic.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Topwintervacations Housatonic, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Housatonic. Places to stay near Housatonic are 1378.83 ft² on average, with prices averaging $503 a night.

Topwintervacations makes it easy and safe to find and compare vacation rentals in Housatonic with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Housatonic

Type Count
Vacation Homes 87
B&B 4
Others 4
Cottages 3
Hotels with Suites 3
Holiday Apartments 2
Cabin Rentals 1
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Housatonic

Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations 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 Housatonic.

Weather in Housatonic

View the weather forecast for Housatonic before booking your Housatonic 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

Complexes around Housatonic, MA