Find Romantic Hotels in Hancock, MA from $100

Start date: Check-in selected.
To Date
End date: Check-out
  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check availability on Hancock Romantic Hotels

Our top choices for Hancock romantic hotels

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Hancock
9.8 out of 10, Exceptional, (20)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
$211 nightly
The price is $236
Dec 10 - Dec 11
Total with taxes and fees
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

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
$92 nightly
The price is $103
Dec 12 - Dec 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1008)
"Great stay!"
United States
Ann
$89 nightly
The price is $100
Dec 17 - Dec 18
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

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
$113 nightly
The price is $126
Dec 14 - Dec 15
Total with taxes and fees
Berkshires Untold

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
$183 nightly
The price is $205
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Red Lion Inn

Berkshire Village Carriage House - Super Private!!

Lanesborough
9.8 out of 10, Exceptional, (269)
"The cottage was amazing. Hope to be visit again and again. "
United States
Mark M.
$188 nightly
The price is $210
Dec 10 - Dec 11
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (548)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
$186 nightly
The price is $208
Dec 14 - Dec 15
Total with taxes and fees
The Williams Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
$204 nightly
The price is $216
Jan 7 - Jan 8, 2026
Total with taxes and fees
Harbour House Inn

1896 House Country Inn & Motels

2.5 star property
Williamstown
6.6 out of 10, (448)
"The price is good. It's a classic motel from the '50's, but gets the job done."
United States
edson
$112 nightly
The price is $126
Dec 23 - Dec 24
Total with taxes and fees
1896 House Country Inn & Motels

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Stephentown
8.4 out of 10, Very Good, (12)
"Great location and property. thank you"
United States
Christine P.
$244 nightly
The price is $260
Dec 14 - Dec 15
Total with taxes and fees
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
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 Hancock

Hancock attractions for couples

Nestled in the scenic Berkshires, Hancock, Massachusetts is a paradise of outdoor adventure and cultural experiences perfect for . Start your journey at Jiminy Peak Mountain Resort, where year-round activities await—from exhilarating skiing and snowboarding in winter to mountain biking and hiking in warmer months, catering to families eager for action. Don’t miss the nearby Massachusetts Museum of Contemporary Art (MASS MoCA) in North Adams, showcasing innovative art installations that will spark your imagination and provide a unique cultural touch to your trip. For a serene escape, explore the vast landscapes of the October Mountain State Forest, where you can hike through tranquil trails, enjoy picnicking, or simply revel in the beauty of nature. Families can also engage in fishing and kayaking at the pristine lakes nearby, perfect for creating cherished memories. When it comes to accommodations, the charming inn options in Hancock offer personalized service and cozy atmospheres, allowing you to unwind after a day of exploration. Staying here not only gives you easy access to these attractions but also immerses you in the peaceful, picturesque surroundings that the Berkshires are known for.

Find the best romantic hotels in Hancock

For couples looking to ignite their romance in the picturesque setting of Hancock, Massachusetts, these hotels offer the perfect blend of comfort and intimacy. Each hotel provides unique amenities that enhance the romantic experience, ensuring a memorable getaway.

Club Wyndham Bentley Brook

  • Why it's great for a couples retreat: For a romantic escape in the scenic Berkshires, Club Wyndham Bentley Brook is an exceptional choice for couples. With an impressive guest review rating of 9.2, this hotel boasts indoor and outdoor pools, a relaxing hot tub, and stunning mountain views that create a serene atmosphere perfect for romance. The premium rooms feature kitchenettes and private terraces, inviting guests to enjoy intimate meals or quiet moments together under the stars.
  • Other amenities: In addition to its romantic offerings, the hotel features a range of amenities to make the stay enjoyable. Guests can take advantage of the fitness center that’s open 24 hours, unwind in the sauna, or enjoy billiards in the game room. Ski enthusiasts will appreciate the nearby ski slopes and the option for ski-in/ski-out access. With free self-parking and a variety of outdoor activities nearby, guests can easily explore the beautiful surroundings while enjoying their romantic getaway.
  • Nearby attractions: Jiminy Peak Mountain Resort - 0.0 miles, Mountain Coaster - 0.55 miles, Alpine Super Slide - 1.05 miles

Mountainside Condo Ski In Ski Out

  • Why it's great for a couples retreat: The Mountainside Condo Ski In Ski Out is a charming retreat for couples looking to enjoy a romantic getaway with a dash of adventure. With a solid review rating of 9.0, this condo features a cozy fireplace and a private kitchen, providing an intimate setting for couples to relax and connect. The hotel’s ski-in/ski-out convenience makes it perfect for winter sports lovers wanting to share exhilarating days on the slopes.
  • Other amenities: In addition to its romantic offerings, the condo provides several appealing amenities. Couples can enjoy the shared pool and hot tub for relaxation or take advantage of the onsite fitness facilities. The picturesque mountain views add to the charm, while the nearby hiking trails promise memorable outdoor experiences together. A dedicated parking area ensures easy access, allowing guests to explore the beautiful surroundings at their own pace.
  • Nearby attractions: Jiminy Peak Mountain Resort - 0.0 miles, Mountain Coaster - 0.2 miles, Alpine Super Slide - 0.71 miles

Jiminy Peak Mountain Resort

  • Why it's great for a couples retreat: Jiminy Peak Mountain Resort is an ideal destination for couples seeking adventure intertwined with romance. Rated 8.2, this resort offers a cozy atmosphere complemented by outdoor pools and inviting hot tubs, perfect for unwinding after a day on the slopes. The stunning mountain views enhance the romantic setting, making it easy for guests to lose themselves in each other's company amidst nature's beauty.
  • Other amenities: Beyond the romantic vibes, the resort provides a wealth of amenities to elevate the experience. Couples can enjoy onsite skiing and snowboarding or take advantage of tennis courts for a fun match together. The option for mountain biking and hiking nearby adds to the adventure. Guests will also find a restaurant offering delicious meals, and a concierge service is available to assist with plans and bookings, ensuring a seamless and enjoyable stay.
  • Nearby attractions: Jiminy Peak Mountain Resort - 0.0 miles, Mountain Coaster - 0.31 miles, Alpine Super Slide - 0.81 miles

Top Hancock Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Hancock?
Are you and your partner in need of a romantic vacation? Our guests also enjoy Hancock for its skiing, hiking, and mountain views. You might consider checking out some of the nearby sights and attractions such as Jiminy Peak Mountain Resort, Alpine Super Slide, or Mountain Coaster. If you're interested in staying near a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Hancock?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Hancock: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Hancock are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Hancock?
There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all that Hancock has to offer. Couples looking for a little of everything will enjoy Hancock for its skiing, hiking, and restaurants. A visit to Jiminy Peak Mountain Resort, Alpine Super Slide, or Mountain Coaster might be just the ticket when you're checking out the sights.
What's the best way to get to Hancock and around town during my romantic getaway?
These transportation options in Hancock might help your romantic trip get off to a smooth start: The closest major airport is Pittsfield, MA (PSF-Pittsfield Municipal), located 8.5 mi (13.6 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.

Explore a world of travel with Expedia