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Find Romantic Hotels in Monterey, MA from $100

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Top Monterey Romantic Hotels

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
$89 nightly
The price is $100
Dec 15 - Dec 16
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (982)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$92 nightly
The price is $103
Dec 12 - Dec 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
$189 nightly
The price is $212
Dec 18 - Dec 19
Total with taxes and fees
The Red Lion Inn

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (807)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
$114 nightly
The price is $127
Dec 9 - Dec 10
Total with taxes and fees
Berkshires Untold

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
$164 nightly
The price is $189
Dec 8 - Dec 9
Total with taxes and fees
Blackberry River Inn

Berkshire Village Carriage House - Super Private!!

Lanesborough
9.8 out of 10, Exceptional, (268)
"The cottage was amazing. Hope to be visit again and again. "
United States
Mark M.
$189 nightly
The price is $211
Dec 8 - Dec 9
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!

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
$204 nightly
The price is $224
Jan 5 - Jan 6, 2026
Total with taxes and fees
Gedney Farm

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
$155 nightly
The price is $172
Jan 5 - Jan 6, 2026
Total with taxes and fees
Gateways Inn & Restaurant

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
$414 nightly
The price is $462
Dec 28 - Dec 29
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
United States
Christopher
$179 nightly
The price is $200
Dec 11 - Dec 12
Total with taxes and fees
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.

Find out more about Monterey

Monterey attractions for couples

Monterey, Massachusetts offers a tranquil escape with a variety of activities that appeal to adventurous travelers and families alike. Start your exploration at the stunning Lake Garfield, where you can enjoy boating, fishing, or simply relaxing by the serene shores. For nature lovers, the nearby Beartown State Forest provides miles of hiking trails that wind through lush woodlands and offer breathtaking views, perfect for family outings or a personal retreat. History enthusiasts will appreciate a visit to the quaint Monterey Museum, featuring local art and historical exhibits that tell the story of this charming town. Don’t miss a stroll through the picturesque village center, where you can discover unique shops and delightful eateries showcasing local cuisine. To truly unwind, consider staying at one of the cozy inns or lodges that provide a homey atmosphere and attentive service, ensuring your family feels pampered. Whether you’re enjoying a morning coffee on a scenic balcony or ending the day by the fire pit, the accommodations in Monterey enhance your exploration with comfort and convenience.

Top Monterey Hotel Reviews

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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