Find Romantic Hotels in The Berkshires, MA
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on The Berkshires Romantic Hotels
Tonight
31 Aug - 1 SepTomorrow
1 Sep - 2 SepThis weekend
4 Sep - 6 SepNext weekend
11 Sep - 13 SepOur top choices for The Berkshires romantic hotels
1. Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!Lanesborough
Maya H.
AED 551
AED 845 total
includes taxes & fees
16 Sep - 17 Sep
2. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country InnHancock
John F.
AED 459
AED 956 total
includes taxes & fees
2 Sep - 3 Sep
3. A roomy remodeled retreat close to MassMoCA
A roomy remodeled retreat close to MassMoCANorth Adams
Jennifer O.
AED 841
AED 1,781 total
includes taxes & fees
9 Sep - 10 Sep
4. A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!Granby
Kristen S.
AED 496
AED 927 total
includes taxes & fees
8 Sep - 9 Sep
5. Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Enjoy a restful stay with fast internet, smart TV and the company of your pet.winsted
Steve
6. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain DenDover
Tania J.
AED 179
AED 1,111 total
includes taxes & fees
2 Sep - 3 Sep
7. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Gorgeous River Views! On Rails to Trails and just steps to quaint CollinsvilleCollinsville
Mike
AED 1,146
AED 1,942 total
includes taxes & fees
10 Sep - 11 Sep
8. Perfect for a peaceful get away in clean fresh Vermont air!
Perfect for a peaceful get away in clean fresh Vermont air!Woodford
Adam a.
View all properties
Top The Berkshires Hotel Reviews
The Red Lion Inn
10/10 Excellent
"The Red Lion Inn is always charming and comfortable!"
The Cornell Inn, Lenox & The Berkshires
10/10 Excellent
"Lovely people and place. Breakfast was great and so was the room. Highly recommend."
Jiminy Peak Mountain Resort
10/10 Excellent
"Nice to have a kitchenette to cook in"
Explore a world of travel with Expedia
- Hotels near Ski Butternut
- Wyndham Hotels in Tyringham
- Motel 6 Hotels in Blandford
- B&B in South Lee
- America's Best Inns Hotels in Chester
- Cheap Hotels in Lee
- Resorts in Becket
- Villas in South Lee
- Cabin Rentals in Monterey
- Historic Hotels in Sheffield
- Accor Hotels in Blandford
- Hotels with a Pool in New Marlborough
- Cottages in The Berkshires
- B&B in The Berkshires
- 2 Star Hotels in Sheffield
- Historic Hotels in Becket
- 3 Star Hotels in Sheffield
- Motels in Great Barrington
- Villas in Tyringham
- Red Carpet Inn Hotels in Blandford
- Cottages in Chester
- Cabin Rentals in Otis
- Guest Houses in South Lee
- Apartments in Becket
- Hotels with an Indoor Pool in The Berkshires
- 5 Star Hotels in Tyringham
- Winery Hotels in The Berkshires
- Hotels with Bars in Great Barrington
- Cottages in Beartown State Forest
- Resorts & Hotels with Spas in Great Barrington
- Cabin Rentals in The Berkshires
- Historic Hotels in South Lee
- Condo Rentals in Lee
- 3 Star Hotels in Blandford
- Hotel Wedding Venues Hotels in Stockbridge
- Great Barrington Hotels
- Daiwa Royal Hotels in Lee
- Independent Hotels in New Marlborough
- 2 Star Hotels in Sandisfield
- Inns in The Berkshires
- Hotel Wedding Venues Hotels in Great Barrington
- Romantic Hotels in Becket
- Casino Hotels in The Berkshires
- Farmstay in The Berkshires
- Inns in Blandford
- Aparthotels in The Berkshires
- Lodges in Chester
- Cabin Rentals in Lee
- Cabin Rentals in Sheffield
- Casino Hotels in Great Barrington
- Pet-Friendly Hotels in New Marlborough
- Wyndham Hotels in Blandford
- 5 Star Hotels in Otis
- Marriott Hotels & Resorts in Chester
- 5 Star Hotels in Sheffield
- Condo Resorts in The Berkshires
- Independent Hotels in Blandford
- Hotels with a Pool in Sheffield
- Family Hotels in Lenox
- Beach Hotels in Stockbridge
- Vacation Homes in Mill River
- 5 Star Hotels in The Berkshires
- 4 Star Hotels in The Berkshires
- Condo Rentals in Mill River
- Boutique Hotels in Lenox
- B&B in Tyringham
- Vacation Homes in New Marlborough
- 5 Star Hotels in Mill River
- Business Hotels in New Marlborough
- Cottages in Sheffield
- Condo Resorts in New Marlborough
- Lodges in The Berkshires
- Hotels with WiFi in Great Barrington
- Hotels with Free Parking in Becket
- 3 Star Hotels in Monterey
- Pet-Friendly Hotels in The Berkshires
- Hotels with Bars in The Berkshires
- Golf Hotels in Great Barrington
- Hotels with Hot Tubs in The Berkshires
- Hotel with a Concierge Hotels in Great Barrington
- Monterey Hotels
- Adults Only Resorts & in Lenox
- Hotels near National Shrine of the Divine Mercy
- Resorts in The Berkshires
- 4 Star Hotels in Sheffield
- Hotels with Hot Tubs in Stockbridge
- Cabin Rentals in South Lee
- B&B in Great Barrington
- 5 Star Hotels in Monterey
- Cabin Rentals in Blandford
- Romantic Hotels in Lee
- 2 Star Hotels in Beartown State Forest