
Luxury rentals in The Berkshires
Find and book unique accommodations on Airbnb
Top-rated luxury vacation rentals in The Berkshires
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 2 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for The Berkshires luxury vacation rentals
Other great luxury vacation rentals in The Berkshires
Luxe

Home in South Cairo
5 out of 5 average rating, 17 reviewsLuna Cove: Premier Hudson Valley Getaway
MalvinaRating, 5 stars1 month ago
The house was incredibly clean and tidy, and very welcoming! The table in the main area was perfect for our dinner of 11 ladies where we could comfortably gather to celebrate, and the upstairs media room was perfect for our karaoke night! This was a beautiful house and space, and we had a wonderful stay!
Luxe

Home in Kerhonkson
4.75 out of 5 average rating, 8 reviewsHome Sweet Hudson: A Retreat @ Hudson Woods
AndyRating, 5 stars3 weeks ago
Excellent stay! The house/property exceeding expectations - the pool house, pool, and living quarters were in great condition and my group really enjoyed the amenities. The house is in a lovely area to just unwind, enjoy the outdoors, and visit some of the local shops/restaurants in the area. Thank you! Would come back again.
Luxe

Home in Hurley
4.95 out of 5 average rating, 21 reviewsFamily Manor Sleeps 18 w Pickleball, Pool, HT, FP
CathyRating, 5 stars2 weeks ago
We had a group of 8 adults and 8 kids ranging from 1-10yo, and there was plenty of space for everything we needed to do! All were entertained and enjoyed the outside and inside spaces, especially the pickleball/basketball area, hot tub, pool (although very cold in May), foosball. There were a few things that didn't work but nothing major and hosts were very responsive with help. Very clean even for a pet-friendly place. Would definitely recommend for large groups with kids of pretty much any age. The hosts also provide a online guide that contains lots of tips and local recommendations, very helpful. Forsyth Nature Center (and playground) and Kingston Farmers Market (both free) were highlights for us.
Luxe

Place to stay in Hyde Park
Historic Vanderbilt Estate Carriage House
BrittanyRating, 5 stars8 months ago
Absolutely amazing stay! This home is everything we hoped for - extremely clean, beautiful decor and such a peaceful property. The owners truly thought of everything. The property is so beautiful - we did not want to leave. We will definitely be back!
Luxe

Home in New Marlborough
5 out of 5 average rating, 3 reviewsSunset Falls: A Berkshire Mountain Luxury Retreat
MichaelRating, 5 stars7 months ago
The place was absolutely stunning and so was the experience. Great host, booking experience, and an epic place! Highly recommend!
Luxe

Home in Catskill
4.96 out of 5 average rating, 28 reviewsSecluded modern home with private creek
ScottRating, 5 stars2 weeks ago
My fiancé and I had a delightful stay. The location is beautiful, perfect for anyone looking for a private getaway. Very beautiful open kitchen and living areas. Host is proactive and responds very quickly. Check in & check out very smooth and straight forward.
Luxe

Place to stay in Lenox
The Kemble Berkshires
Destinations to explore
- Rentals with a hot tub The Berkshires
- Rentals with a patio The Berkshires
- Rentals with a home theater The Berkshires
- Rentals with a kayak The Berkshires
- Beachfront rentals The Berkshires
- Rentals with an accessible height toilet The Berkshires
- Fitness-friendly rentals The Berkshires
- Waterfront rentals The Berkshires
- Cabin rentals The Berkshires
- Rentals with a washer and dryer The Berkshires
- Rentals with beach access The Berkshires
- Cottage rentals The Berkshires
- Pet-friendly rentals The Berkshires
- Smoking-friendly rentals The Berkshires
- Rentals with a fireplace The Berkshires
- Chalet rentals The Berkshires
- Condo rentals The Berkshires
- Rentals with a fire pit The Berkshires
- Guesthouse rentals The Berkshires
- Ski-in/ski-out rentals The Berkshires
- Kid-friendly rentals The Berkshires
- Aparthotel rentals The Berkshires
- Family-friendly rentals The Berkshires
- Private suite rentals The Berkshires
- Boutique hotel rentals The Berkshires
- Villa rentals The Berkshires
- House rentals The Berkshires
- Rentals with a sauna The Berkshires
- Bed and breakfasts The Berkshires
- Rentals with lake access The Berkshires
- Farmstay rentals The Berkshires
- Vacation home rentals The Berkshires
- Rentals with pools The Berkshires
- Rentals with outdoor seating The Berkshires
- Townhouse rentals The Berkshires
- Apartment rentals The Berkshires
- Hotel rentals The Berkshires
- Rentals with breakfast The Berkshires
- Lakehouse rentals The Berkshires
- Rentals with an EV charger The Berkshires
- Luxury rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom