Housatonic Holiday Rentals

Compare Villas, Resorts, & Rentals in Housatonic, Massachusetts, USA

Granville House
FromUS $307 per night
|
10.0 (101 Reviews)
1 Bedroom 2 Guests
Too Good AKA 2 Goodrich St
|
10.0 (2 Reviews)
8 Bedrooms 8 Guests
Renovated Private Guest House by Evergreen Home
10.0 (9 Reviews)
2 Bedrooms 5 Guests
Beautiful House in the Woods, Huge Yard, Hot Tub
10.0 (1 Review)
4 Bedrooms 8 Guests
The Little Lion
FromUS $98 per night
|
8.6 (562 Reviews)
1 Bedroom 2 Guests
Fabulous Apartment - Great Barrington
10.0 (3 Reviews)
2 Bedrooms 4 Guests
Tranquil 3 BR Stockbridge House w/Private Deck!
|
9.5 (2 Reviews)
3 Bedrooms 6 Guests
Great Barrington Lakeside Getaway w/Kayak & Grill
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9.3 (3 Reviews)
4 Bedrooms 10 Guests
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
|
8.0 (1 Review)
6 Bedrooms 14 Guests
Lakefront Berkshires Retreat w/Deck, Dock & Boat!
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7.5 (4 Reviews)
4 Bedrooms 10 Guests
Tranquil 3 BR Stockbridge House w/Private Deck!
10.0 (95 Reviews)
3 Bedrooms 6 Guests
Stockbridge Retreat w/Pool & Hot Tub!
|
New
4 Bedrooms 10 Guests
Just a min from Downtown Stockbridge on 11 Acres
10.0 (78 Reviews)
4 Bedrooms 8 Guests
Woodland Zen by AvantStay
FromUS $1,342 per night
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New
3 Bedrooms 6 Guests
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
10.0 (57 Reviews)
5 Bedrooms 16 Guests
Twin Maple Farm: Charming Modern Farmhouse
10.0 (49 Reviews)
4 Bedrooms 8 Guests
Classic Stockbridge Cottage
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New
4 Bedrooms 8 Guests
Renovated Colonial on the River! Fantastic Views
10.0 (44 Reviews)
3 Bedrooms 5 Guests
A Charming Mid 1800's Stockbridge Farmhouse.
10.0 (34 Reviews)
4 Bedrooms 6 Guests
Granville House
FromUS $275 per night
|
New
5 Bedrooms 14 Guests
Stockbridge Home, Come Experience The Berkshires!
10.0 (33 Reviews)
3 Bedrooms 6 Guests
The Little Lion
FromUS $175 per night
7.4 (193 Reviews)
16 Bedrooms 8 Guests
Secluded Family Home in Serene Stockbridge Woods
10.0 (24 Reviews)
3 Bedrooms 8 Guests
Classic Stockbridge Cottage
10.0 (17 Reviews)
4 Bedrooms 8 Guests
Beautiful House in the Woods: Huge Yard, Hot Tub
10.0 (9 Reviews)
4 Bedrooms 8 Guests
Spacious & Modern Berkshires Getaway
10.0 (8 Reviews)
3 Bedrooms 7 Guests
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
10.0 (6 Reviews)
3 Bedrooms 8 Guests
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
10.0 (5 Reviews)
6 Bedrooms 14 Guests
Outdoor Sauna, Hot tub, Fire Pit, Dogs Welcome!
10.0 (4 Reviews)
3 Bedrooms 6 Guests
1 Mi to Dtwn: Cottage w/Large Yard in Stockbridge
10.0 (4 Reviews)
4 Bedrooms 8 Guests
Luxuriously Comfortable Country Home
10.0 (2 Reviews)
7 Bedrooms 14 Guests
Loft Style Cabin In West Stockbridge, Book Now!
10.0 (2 Reviews)
4 Bedrooms 8 Guests
Charming Summer Cottage ~ Dog Friendly
10.0 (2 Reviews)
3 Bedrooms 6 Guests
Charming Long Pond Vacation Home in the Berkshires
10.0 (1 Review)
4 Bedrooms 8 Guests
Stay Lakeside This Summer!
9.8 (80 Reviews)
3 Bedrooms 6 Guests
Sweet Cozy Victorian in Housatonic. Close to everything.
9.8 (6 Reviews)
3 Bedrooms 6 Guests
Beautiful House In The Woods, Huge Yard, Hot Tub
9.6 (21 Reviews)
4 Bedrooms 8 Guests
Historic 4-bedroom riverside home in Berkshires
9.6 (8 Reviews)
4 Bedrooms 8 Guests
Spacious & Serene Berkshires Retreat In The Woods
8.4 (5 Reviews)
7 Bedrooms 14 Guests
Greek Revival Farmhouse in Stockbridge
New
3 Bedrooms 6 Guests
Modern Cottage Minutes from Downtown Great Barrington
10.0 (32 Reviews)
4 Bedrooms 10 Guests
Morgan's Millhouse (Front)
9.8 (9 Reviews)
3 Bedrooms 8 Guests
Entire home hosted by Morgan
9.6 (4 Reviews)
1 Bedroom 2 Guests

About Casai's Private Villas and Holiday Rentals in Housatonic

Discover more than 106 vacation rentals available in Housatonic. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Housatonic.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Housatonic, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Housatonic. On average, places to stay near Housatonic offer 1442.96 ft², with nightly prices averaging US $552.

With Casai, finding and comparing holiday rentals in Housatonic is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Frequently Asked Questions About Housatonic?

What are the top holiday rentals in Housatonic?

How many Casai.com holiday rentals are available in Housatonic?

As of 2026, Casai boasts over 106 properties listed in the Housatonic area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Housatonic.