Find Winery Hotels in Western Massachusetts, MA

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Western Massachusetts Winery Hotels

Top Western Massachusetts Winery Hotels

Our top choices for Western Massachusetts hotels with winery

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is NT$3,727
NT$4,163 total
includes taxes & fees
Sep 21 - Sep 22
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Comfort Inn & Suites Sturbridge - Brimfield
Exterior

Comfort Inn & Suites Sturbridge - Brimfield

2.5 star property
9.0 out of 10, Wonderful, (1003)
"The facilities were very clean and the staff were great. The room was great and the bed was comfy. I would stay there again."
The price is NT$3,573
NT$3,991 total
includes taxes & fees
Sep 29 - Sep 30
Comfort Inn & Suites Sturbridge - Brimfield
D. Hotel Suites & Spa
Indoor pool

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2230)
"Very nice hotel with great rooms for affordable price"
The price is NT$3,913
NT$4,546 total
includes taxes & fees
Sep 16 - Sep 17
D. Hotel Suites & Spa
Hotel Northampton
2 restaurants, breakfast, lunch, dinner served; American cuisine

Hotel Northampton

3.5 star property
9.2 out of 10, Wonderful, (1003)
"Beautiful historic property with great dining options."
Hotel Northampton
Hampton Inn & Suites Springfield/Downtown
Lobby

Hampton Inn & Suites Springfield/Downtown

2.5 star property
8.6 out of 10, Excellent, (1004)
"Plenty of parking.. nice breakfast! "
The price is NT$3,830
NT$4,345 total
includes taxes & fees
Oct 5 - Oct 6
Hampton Inn & Suites Springfield/Downtown
East Rock Inn
Premium Apartment | Private kitchen | Electric kettle

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (32)
"Room was really comfortable and clean. Beautiful views from the main court yard during the day and at night the sky was full of stars. Amazing. "
The price is NT$4,656
NT$5,201 total
includes taxes & fees
Sep 28 - Sep 29
East Rock Inn
Courtyard by Marriott West Springfield
View from property

Courtyard by Marriott West Springfield

3.0 star property
9.2 out of 10, Wonderful, (518)
"Exceptionally satisfying stay in all aspects "
The price is NT$4,497
NT$5,147 total
includes taxes & fees
Oct 5 - Oct 6
Courtyard by Marriott West Springfield
Quality Inn & Suites Northampton - Amherst
Deluxe Room, 2 Queen Beds, Non Smoking | Desk, iron/ironing board, cribs/infant beds, rollaway beds

Quality Inn & Suites Northampton - Amherst

2.5 star property
7.2 out of 10, Good, (1001)
"great location - just off the highway and near to downtown"
The price is NT$3,830
NT$4,278 total
includes taxes & fees
Sep 21 - Sep 22
Quality Inn & Suites Northampton - Amherst
Nautical Nest
Premium bedding, memory foam beds, individually decorated

Nautical Nest

2.5 star property
9.6 out of 10, Exceptional, (118)
"Great location. Room needs a comfy chair"
The price is NT$4,681
NT$5,430 total
includes taxes & fees
Sep 22 - Sep 23
Nautical Nest
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (561)
"Super "
The price is NT$5,035
NT$5,624 total
includes taxes & fees
Sep 28 - Sep 29
Berkshire Valley 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.

Top Western Massachusetts Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"Room very comfortable and clean; appreciated free wifi, breakfast, coffee, iron and hairdryer. But best of all, the warm welcome that Brian at the Reception Desk gave us and all the information he gave about Great Barrington, excellent recommendations on dining spots and, especially, telling us about the Clark Arts Institute in nearby Williamstown which was the highlight of our trip to The Berkshires. Thank you so much Brian for your wonderful service."
Ian 2-night trip
Posted 7 days ago
Quality Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"We booked for an overnight stay to attend a concert at Tanglewood and were pleasantly surprised by the quality of the room for the price; clean, large, updated, comfy. Great value!"
Anonymous traveler 1-night trip
Posted 9 days ago
Howard Johnson by Wyndham Lenox

Explore a world of travel with Expedia

Explore a world of travel with Expedia