Holiday rentals near Housatonic River
We found 1,847 holiday rentals — enter your dates for availability
Take a look at holiday rentals close to Housatonic River that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Housatonic River
Showing deals for:27 Feb - 6 Mar
Image gallery for Waterfront Cottage 10 Min From Great Barrington
10 out of 10, Exceptional, (99 reviews)
Exceptional
(99 reviews)
Waterfront Cottage 10 Min From Great Barrington
Great Barrington, MA
8% off
Price is NZ$4,445
for 7 nights, 1 cottage
NZ$635 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Housatonic River
Showing deals for: 22 Feb - 25 Feb
Pet Friendly Riverfront Home in Great Barrington
Sleeps 8 · 3 bedrooms · 1 bathroom
9.2 out of 10
wonderful
(5 reviews)
The current price is NZ$1,523
for 3 nights, 1 home
NZ$508 per night
includes taxes & fees
Top rated rentals - Housatonic River
In town to check out Fairfield University
10 out of 10
exceptional
(15 reviews)
We were looking to book a shorter week in Fairfield to check out the university. This property allowed a shorter stay, which was extremely convenient for us. The location was a short drive to the university and within walking distance to the beach. The house itself was absolutely gorgeous. All levels were tastefully decorated, the house was clean, well lit, and included all modern amenities. The hosts were very attentive to our needs and responded in a timely manner. I would not hesitate to stay here again. One of the most beautiful properties I’ve ever stayed at near the beach.
Coleen C.
Stayed Jul 2025
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value