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Find Romantic Hotels in Monterey, MA

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Check availability on Monterey Romantic Hotels

Tonight
31 Oct - 1 Nov
Tomorrow
1 Nov - 2 Nov
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Top Monterey Romantic Hotels

Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (934)
"Enjoyable stay. Staff were very nice. "
United States
Claire
The price is AED 378
AED 423 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1023)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
The price is AED 393
AED 439 total
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (787)
"We enjoyed our stay , bar tender was excellent "
United States
Connie
The price is AED 340
AED 380 total
includes taxes & fees
5 Nov - 6 Nov
Berkshires Untold
Library
Blackberry River Inn
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (151)
"A wonderful facility, lovely breakfast and way way more than you would expect in every catagory."
United States
Steve
The price is AED 598
AED 687 total
includes taxes & fees
3 Nov - 4 Nov
Blackberry River Inn
Outdoor pool, sun loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1024)
"Wonderful old inn; chock full of charm."
United States
Karen
The price is AED 510
AED 734 total
includes taxes & fees
16 Nov - 17 Nov
The Red Lion Inn
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (263)
"This VRBO was perfect for what I needed. The property was gorgeous, the house was clean, and it had everything I needed for a nice stay. Thank you! "
United States
Britt F.
The price is AED 496
AED 771 total
includes taxes & fees
4 Nov - 5 Nov
Berkshire Village Carriage House - Super Private!!
Front of property
The Constance by the Lenox Collection
The Constance by the Lenox Collection
3.5 star property
8.4 out of 10, Very Good, (558)
"Great b&b, great Bfast, great location, easy parking!"
United States
Rose
The price is AED 398
AED 444 total
includes taxes & fees
3 Nov - 4 Nov
The Constance by the Lenox Collection
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (162)
"Inn was gorgeous and staff exceptional!"
United States
Joyce
Brook Farm Inn
Front of property
Gedney Farm
Gedney Farm
3.5 star property
9.2 out of 10, Wonderful, (131)
"Great property"
United States
Blair
Gedney Farm
Property grounds
Whistler's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (500)
"Cozy spot with very friendly propeietor"
United States
Kyle
The price is AED 562
AED 628 total
includes taxes & fees
9 Nov - 10 Nov
Whistler's Inn Bed & Breakfast
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Clean room and very friendly staff. "
Michael 2-night trip
Posted 13 hours ago
The Red Lion Inn

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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.