Find Romantic Hotels in Lenox, MA from $100

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Top Lenox 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 14 - Dec 15
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, (980)
"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

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 7 - Dec 8
Total with taxes and fees
Berkshires Untold

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
$154 nightly
The price is $171
Jan 5 - Jan 6, 2026
Total with taxes and fees
Gateways Inn & Restaurant

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

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
$184 nightly
The price is $206
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Red Lion Inn

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (546)
"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 9 - Dec 10
Total with taxes and fees
The Williams 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
$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!!

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
$249 nightly
The price is $264
Jan 5 - Jan 6, 2026
Total with taxes and fees
Harbour House 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 Lenox

Lenox attractions for couples

Lenox, Massachusetts, is a captivating blend of culture and nature, perfect for travelers seeking quality experiences. Begin your exploration at Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy world-class performances in a stunning outdoor setting. A visit to the Norman Rockwell Museum is a must, showcasing the works of one of America's most beloved illustrators, with a collection that captures the spirit of American life. For outdoor enthusiasts, the nearby Kennedy Park offers a network of trails ideal for hiking and biking, surrounded by picturesque landscapes. Families can enjoy a day at the Berkshire Botanical Garden, where you can wander through beautifully curated gardens and enjoy seasonal workshops. As for accommodations, the charming inns and upscale hotels in the heart of Lenox provide a cozy yet refined experience, often featuring amenities like spa services and gourmet dining. Staying here allows you to easily explore the town's vibrant arts scene and enjoy the natural beauty that the Berkshires offer, all while receiving attentive service that caters to your every need.

Find the best romantic hotels in Lenox

For couples seeking a romantic escape in Lenox, Massachusetts, these hotels provide the perfect backdrop for a memorable getaway. Each offers unique amenities that enhance the romantic experience.

The Yankee, Trademark Collection by Wyndham

  • Why it's great for a couples retreat: With a solid review rating of 9.2, The Yankee, Trademark Collection by Wyndham presents a charming setting for couples. This hotel features a private hot tub, perfect for relaxing evenings together, and a cozy fireplace that adds warmth to your stay. Guests can enjoy a delightful buffet breakfast to fuel their adventures, ensuring a wonderful start to each romantic day.
  • Other amenities: Other highlights include balconies or patios for private moments, a 24-hour fitness center for those who want to stay fit, and concierge services to assist with local recommendations. The indoor pool offers a relaxing escape, and the hotel’s nearby skiing and hiking locations provides opportunities for outdoor exploration, adding more excitement to your romantic getaway.
  • Nearby attractions: Pleasant Valley Wilderness Sanctuary - 1.21 miles, Herman Melville's Arrowhead - 1.65 miles, Kennedy Park - 1.79 miles

The Cornell Inn, Lenox & The Berkshires

  • Why it's great for a couples retreat: The Cornell Inn, Lenox & The Berkshires, a review rating of 9.2, offers an enchanting retreat for couples. With private hot tubs available, guests can indulge in romantic evenings while the cozy decor and fireplace create an intimate atmosphere. A complimentary full breakfast is served daily, perfect for sharing moments over delicious food before heading out to explore the Berkshires.
  • Other amenities: This charming inn features outdoor terraces and balconies allowing guests to enjoy the beautiful surroundings together. Guests can also enjoy self-parking and daily housekeeping for added convenience. With nearby access to skiing and biking, couples can adventure together, making it a fantastic choice for romance amid nature's beauty.
  • Nearby attractions: Kennedy Park - 1.04 miles, Lenox Library - 0.62 miles, Ventfort Hall Mansion and Gilded Age Museum - 1.0 miles

Hampton Inn & Suites Berkshires-Lenox

  • Why it's great for a couples retreat: The Hampton Inn & Suites Berkshires-Lenox is an inviting choice for couples looking to unwind together, an impressive review rating of 9.2. Guests can enjoy an indoor pool for a cozy swim, along with complimentary breakfast options to start the day off right. The hotel's atmosphere encourages intimacy, with comfortable suites featuring separate living areas for added privacy.
  • Other amenities: Additional features include a fitness center for those wanting to stay active, scenic mountain views to set the mood, and convenient access to nearby outdoor activities like hiking and snowboarding. Guests can also take advantage of self-parking and daily housekeeping to ensure a stress-free stay, making it an ideal romantic retreat.
  • Nearby attractions: Pleasant Valley Wilderness Sanctuary - 1.0 miles, Herman Melville's Arrowhead - 1.43 miles, Kennedy Park - 1.58 miles

Courtyard by Marriott Lenox Berkshires

  • Why it's great for a couples retreat: The Courtyard by Marriott Lenox Berkshires offers a delightful setting for couples, with a solid review rating of 9.2. The indoor pool serves as a perfect spot for relaxation, while the comfortable suites provide ample space for couples to unwind after a day of exploring the area. Guests can enjoy a complimentary breakfast that sets the tone for a wonderful day together.
  • Other amenities: Additional amenities include a fitness center to keep active together, self-parking for convenience, and a snack bar for quick bites. The hotel’s inviting atmosphere, combined with its accessible pool and charming surroundings, ensures a memorable romantic experience for guests.
  • Nearby attractions: Pleasant Valley Wilderness Sanctuary - 0.99 miles, Kennedy Park - 0.31 miles, Lenox Library - 1.59 miles

Berkshires Untold

  • Why it's great for a couples retreat: Berkshires Untold stands out as a romantic destination with a guest review rating of 9.0. This hotel offers couples dining experiences and champagne service, ensuring every moment spent here feels special. The beautiful garden views from the restaurant create a serene backdrop for couples to connect and relax.
  • Other amenities: Additional amenities include a terrace for enjoying the outdoors, concierge services for personalized recommendations, and luxurious bathrobes provided for a touch of elegance. With designer toiletries and premium bedding, guests will feel pampered throughout their stay. The hotel’s design and atmosphere foster romance, making it an ideal choice for couples looking to celebrate love.
  • Nearby attractions: Pleasant Valley Wilderness Sanctuary - 0.68 miles, Kennedy Park - 0.53 miles, The Bookstore - 2.15 miles

Top Lenox Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Lenox?
Are you and your partner in need of a romantic vacation? Our guests also enjoy Lenox for its museums, live music, and gardens. If you want to explore the area, you might head to Ventfort Hall Mansion and Gilded Age Museum, Shakespeare and Company, or Tanglewood Music Center. If you're interested in staying near a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Lenox?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Lenox: 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 27°F. The snowiest months in Lenox are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Lenox?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all that Lenox has to offer. Couples looking for a little of everything will enjoy Lenox for its museums, live music, and gardens. You might think about visiting Ventfort Hall Mansion and Gilded Age Museum, Shakespeare and Company, or Tanglewood Music Center.
What's the best way to get to Lenox and around town during my romantic getaway?
This information about transportation options in Lenox might help your romantic getaway go off without a hitch: Make your way to Lenox with a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest major airport located 4.7 mi (7.6 km) from the city center. If you'd like to venture out around the area, consider renting a car to take in more sights.

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