Search for Cheap Deals on
Romantic Hotels in Western Massachusetts

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!


Featured Western Massachusetts Romantic Hotels

D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
Fully refundable
Stay at this 3-star spa hotel in Holyoke. Enjoy free breakfast, free parking, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. ...
D. Hotel Suites & Spa
Shaker Mill Inn
Shaker Mill Inn
2.5 out of 5
2 Oak Street, West Stockbridge, MA
Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Ebenezer II Gifts and Antiques and Hotchkiss ...
Shaker Mill Inn
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a health club, and in-room massages. Our guests praise the helpful staff in our ...
Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
Fully refundable
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Chestnut Lodge
Chestnut Lodge
3.5 out of 5
75 Chestnut Street, Lee, MA
Stay at this 3.5-star guesthouse in Lee. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Goose Pond Reservation and Lee Premium Outlets ...
Chestnut Lodge
Kemble Inn
Kemble Inn
3.5 out of 5
2 Kemble Street, Lenox, MA
Stay at this 3.5-star boutique inn in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Ventfort Hall Mansion and Gilded Age Museum ...
Kemble Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels with Hot Tubs in Western Massachusetts

D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
Stay at this 3-star spa hotel in Holyoke. Enjoy free breakfast, free parking, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. ...
D. Hotel Suites & Spa
Homewood Suites by Hilton Holyoke-Springfield/North
Homewood Suites by Hilton Holyoke-Springfield/North
3 out of 5
375 Whitney Ave, Holyoke, MA
Stay at this 3-star business-friendly hotel in Holyoke. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Homewood Suites by Hilton Holyoke-Springfield/North
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
Book a stay at this spa hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Hotels in Western Massachusetts

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chesterwood and Norman Rockwell Museum ...
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Hotel Northampton
Hotel Northampton
3.5 out of 5
36 King Street, Northampton, MA
Stay at this 3.5-star historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Hotel Northampton
The Orchards Hotel
The Orchards Hotel
2.5 out of 5
222 Adams Rd, Williamstown, MA
Book a stay at this business-friendly hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hopkins Observatory and Williams ...
The Orchards Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Romantic Hotels in Western Massachusetts

Looking to pop the big question? Book a romantic hotel. Digging yourself out of the doghouse? Book a romantic hotel. Regardless of the reason for spoiling your partner, a romantic hotel in Western Massachusetts will do the trick.

What’s love got to do with it?

Pick a flirty place with a secluded pool and private cabanas or go for one with an in-room hot tub and a swanky restaurant on-site. Some hotels in Western Massachusetts even offer romantic packages, so you can really crank up the heat. Did someone say couple’s massages? Yes, please!

Maybe it’s the little things like a ridiculously good view from your balcony or the bottle of bubbly waiting for you when you arrive, but whatever it is, your sweetie is going to flip when they see the romantic resort you booked in Western Massachusetts. Just imagine the fun you’ll have with a place all to yourselves.

Love your hotel; love your savings

You’ll find yourself falling for a lot more than your honey when you book a romantic hotel in Western Massachusetts. You and your partner will have hearts in your eyes when you set your sights on our swoon-worthy hotel rates. Filter hotels by:

  • Hotwire Hot Rates: Snag a Hotwire Hot Rate and you’ll find out the name of your hotel after you book. It’s like the best blind date ever.

  • Price: With rooms starting at $111, your heart may skip a beat when you see how low our prices go on Romantic hotels.

  • Amenities: Room with a view? Fancy restaurant? Room service? Sort through our amenities to find whatever puts you two in the mood.

We’re no doctor of love, but we’ve got some advice for you, don’t wait for a reason to book a romantic hotel. Surprise your honey with a getaway to Western Massachusetts for no reason at all. Spice it with up a Hotwire Hot Rate—after all, every good relationship loves a little mystery.