Find Romantic Hotels in Monterey, MA

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Check availability on Monterey Romantic Hotels

Tonight
Jan 28 - Jan 29
Tomorrow
Jan 29 - Jan 30
This weekend
Jan 30 - Feb 1
Next weekend
Feb 6 - Feb 8

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, (1,012 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is NT$2,915
NT$3,256 total
includes taxes & fees
Feb 5 - Feb 6
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, (1,000 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is NT$3,084
NT$3,444 total
includes taxes & fees
Feb 6 - Feb 7
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (844 reviews)
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
The price is NT$2,778
NT$3,103 total
includes taxes & fees
Jan 29 - Jan 30
Berkshires Untold
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,007 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is NT$5,003
NT$6,994 total
includes taxes & fees
Feb 22 - Feb 23
The Red Lion Inn
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (167 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is NT$5,171
NT$5,947 total
includes taxes & fees
Jan 29 - Jan 30
Blackberry River Inn
Front of property

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (135 reviews)
"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$5,836
NT$6,403 total
includes taxes & fees
Feb 11 - Feb 12
Gedney Farm
Front of property

Gateways Inn & Restaurant

Gateways Inn & Restaurant
3.0 star property
Lenox
8.0 out of 10, Very Good, (197 reviews)
"Gateways Inn is a fantastic place to stay! The staff was very courteous and the room was spacious and very clean. The breakfast was included and very tasty. I highly suggest a stay there if you are planning on visiting the Berkshires!!!"
United States
Miguel
The price is NT$5,260
NT$6,138 total
includes taxes & fees
Jan 29 - Jan 30
Gateways Inn & Restaurant
Suite, Private Bathroom (RedBird Suite) | View from room

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 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is NT$9,737
NT$11,780 total
includes taxes & fees
Feb 16 - Feb 17
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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.
View all properties

Top Monterey Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The room was large, clean and comfortable. The breakfast was good and the staff was great. The hotel is a little bit quaint which I enjoy and why I go there. The only issue was the shower took a while for the water to heat up."
Thomas 1-night trip
Posted 6 days ago
The Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"generally good"
jonathan 1-night trip
Posted 9 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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.

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