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Find Romantic Hotels in Monterey, MA

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Check availability on Monterey Romantic Hotels

Our top choices for Monterey romantic hotels

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1008)
"Great stay there!! Very friendly staff"
United States
Ann
The price is NT$2,783
NT$3,109 total
includes taxes & fees
Dec 17 - Dec 18
The Yankee, Trademark Collection by Wyndham
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (983)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is NT$2,750
NT$3,072 total
includes taxes & fees
Dec 12 - Dec 13
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is NT$4,708
NT$6,653 total
includes taxes & fees
Jan 6 - 2026/1/7
The Red Lion Inn
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (811)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is NT$3,419
NT$3,819 total
includes taxes & fees
Dec 11 - Dec 12
Berkshires Untold
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (163)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is NT$5,125
NT$5,893 total
includes taxes & fees
Dec 11 - Dec 12
Blackberry River Inn
Front of property
Gedney Farm

Gedney Farm

3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (132)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is NT$5,784
NT$6,345 total
includes taxes & fees
Dec 11 - Dec 12
Gedney Farm
Room (King Room) | Iron/ironing board, free WiFi, bed sheets
Gateways Inn & Restaurant

Gateways Inn & Restaurant

3.0 star property
Lenox
8.0 out of 10, Very Good, (192)
"Very well kept property, nice restaurant and is in a great area"
United States
Josephine
The price is NT$4,790
NT$5,590 total
includes taxes & fees
Jan 4 - 2026/1/5
Gateways Inn & Restaurant
Business center
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 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is NT$11,909
NT$14,407 total
includes taxes & fees
Jan 5 - 2026/1/6
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm 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.
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Top Monterey Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly. "
Brendan 1-night trip
Posted 5 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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Frequently asked questions

Searching for romantic hotels in Monterey?
Are you looking for a romantic vacation? If you want to explore the area, you might head to Bidwell House Museum. If you're interested in staying close to a certain attraction, you can sort by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Monterey?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Monterey: The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Monterey are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Monterey?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all that Monterey has to offer. Bidwell House Museum is one of the local sights that might be worth a stop.
What's the best way to get to Monterey and around town during my romantic getaway?
These transportation options in Monterey might help your romantic trip get off to a smooth start: Make your way to Monterey with a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest major airport located 17.5 mi (28.1 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.