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Our top choices for Lenox romantic hotels
1. Garden Gables
Garden Gables4.0 star property
Lenox
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)
"Lovely place!"
"Lovely place!"
Eyee
The price is NT$4,294
NT$4,294
NT$7,184 total
includes taxes & fees
Nov 16 - Nov 17
2. The Yankee Inn
The Yankee Inn2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
9.2/10
Wonderful
(1,004 reviews)
"The location was good for our trip."
"The location was good for our trip."Basil
The price is NT$4,143
NT$4,143
NT$4,627 total
includes taxes & fees
Dec 12 - Dec 13
3. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel3.0 star property
Lee
9.2 out of 10, Wonderful, (1,004 reviews)
9.2/10
Wonderful
(1,004 reviews)
"clean room - pleasant staff"
"clean room - pleasant staff"Tina
The price is NT$3,493
NT$3,493
NT$3,902 total
includes taxes & fees
Dec 13 - Dec 14
4. Berkshires Untold
Berkshires Untold3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,074 reviews)
9.0/10
Wonderful
(1,074 reviews)
"Nice Hotel"
"Nice Hotel"Juan
The price is NT$3,457
NT$3,457
NT$3,862 total
includes taxes & fees
Nov 17 - Nov 18
5. The Whitlock
The Whitlock2.0 star property
Lenox
8.4 out of 10, Very good, (420 reviews)
8.4/10
Very good
(420 reviews)
"Nice location."
"Nice location."Beverly
The price is NT$4,241
NT$4,241
NT$4,737 total
includes taxes & fees
Nov 17 - Nov 18
6. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,001 reviews)
9.4/10
Exceptional
(1,001 reviews)
"Lovely room, comfortable bed and a nice breakfast."
"Lovely room, comfortable bed and a nice breakfast."
judith
The price is NT$5,590
NT$5,590
NT$6,411 total
includes taxes & fees
Nov 16 - Nov 17
7. Berkshire Mountain Lodge
Berkshire Mountain Lodge3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,274 reviews)
9.0/10
Wonderful
(1,274 reviews)
"Excellent stay!!!!"
"Excellent stay!!!!"Susan J
The price is NT$2,523
NT$2,523
NT$3,553 total
includes taxes & fees
Dec 6 - Dec 7
8. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,001 reviews)
9.2/10
Wonderful
(1,001 reviews)
"Nice place to stay"
"Nice place to stay"Michael
The price is NT$3,633
NT$3,633
NT$4,701 total
includes taxes & fees
Nov 16 - Nov 17
9. Chambery Inn
Chambery Inn3.0 star property
Lee
9.6 out of 10, Exceptional, (390 reviews)
9.6/10
Exceptional
(390 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."Alexandra
The price is NT$6,924
NT$6,924
NT$7,734 total
includes taxes & fees
Dec 15 - Dec 16
10. Devonfield Inn B&B
Devonfield Inn B&B4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
10/10
Exceptional
(141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
"Wonderful location and hosts are amazing. Breakfast was great. Clean."Sebastien
The price is NT$12,132
NT$12,132
NT$13,551 total
includes taxes & fees
Nov 16 - Nov 17
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.
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.
Top Lenox Hotel Reviews
Devonfield Inn B&B
Devonfield Inn B&BLee
10/10 Excellent
The history behind the inn was great. Doug one of the owners could not have been any more hospitable. He made sure to go above and beyond throughout our entire stay. Our room was comfortably sized and the fireplace was a great perk to have at night. Breakfast and treats were delicious. We will be back!
The history behind the inn was great. Doug one of the owners could not have been any more hospitable. He made sure to go above and beyond throughout our entire stay. Our room was comfortably sized and the fireplace was a great perk to have at night. Breakfast and treats were delicious. We will be back!
Anonymous traveler
Prospect Berkshires
Prospect BerkshiresEgremont
10/10 Excellent
So fantastic!! The cabins are gorgeous and very well appointed. We are going back!
So fantastic!! The cabins are gorgeous and very well appointed. We are going back!
Emily
Inn at Silver Maple Farm
Inn at Silver Maple FarmEast Chatham
10/10 Excellent
This is a super clean, comfortable, and relaxing Inn. The Inn-keepers, Chloe and Shawn are wonderful. I could not have been happier with the service, the level of cleanliness, and the comfort of my room and common areas. Breakfast was delicious!
This is a super clean, comfortable, and relaxing Inn. The Inn-keepers, Chloe and Shawn are wonderful. I could not have been happier with the service, the level of cleanliness, and the comfort of my room and common areas. Breakfast was delicious!
Michelle
Wilder House Berkshires
Wilder House BerkshiresSheffield
10/10 Excellent
Clean, cozy, and charming. The breakfast is delicious and all went smoothly.
Clean, cozy, and charming. The breakfast is delicious and all went smoothly.
Liliana
Brook Farm Inn
Brook Farm InnLenox
10/10 Excellent
We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!
We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!
roberta
Hotel On North
Hotel On NorthPittsfield
10/10 Excellent
The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...
The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...
Steve
Shaker Mill Inn
Shaker Mill InnWest Stockbridge
10/10 Excellent
This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...
This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...
Joe
Chambery Inn
Chambery InnLee
10/10 Excellent
The building is like going back in time -- the separate boys and girls stairways, the chalkboards in the rooms and historical pictures on the walls.
Breakfast was so well done, selections and presentation were wonderful. Room was extremely comfortable, especially the seating area for watching tv. Lots of nice restaurants and shops within walking distance.
The building is like going back in time -- the separate boys and girls stairways, the chalkboards in the rooms and historical pictures on the walls.
Breakfast was so well done, selections and presentation were wonderful. Room was extremely comfortable, especially the seating area for watching tv. Lots of nice restaurants and shops within walking distance.
Elaine
East Rock Inn
East Rock InnGreat Barrington
10/10 Excellent
Great room, recently renovated. Very close to Butternut and other areas of interest.
Great room, recently renovated. Very close to Butternut and other areas of interest.
Heather
Little Cat Lodge
Little Cat LodgeCopake Falls
10/10 Excellent
I didn't want to leave and wish I had time to stay longer. Room was exceptional. Staff was exceptional. A truly great stay.
I didn't want to leave and wish I had time to stay longer. Room was exceptional. Staff was exceptional. A truly great stay.
Elisabeth
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The BerkshiresLenox
10/10 Excellent
VERY friendly staff and location for area attractions.
VERY friendly staff and location for area attractions.
Lawrence
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 ChesterwoodStockbridge
10/10 Excellent
Diane is an absolutely lovely host--and breakfast at their table is a great experience.
Diane is an absolutely lovely host--and breakfast at their table is a great experience.
Charles
The Yankee Inn
The Yankee InnLenox
10/10 Excellent
We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!
We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!
Colleen
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
10/10 Excellent
A dog barking during the night
A dog barking during the night
Sheila
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Holiday Inn Club Vacations Oak n' Spruce Resort in the BerkshiresSouth Lee
10/10 Excellent
I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...
I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...
David
The Old Inn On The Green
The Old Inn On The GreenGreat Barrington
10/10 Excellent
Truly enjoyed the stay. Peter and his staff were extremely helpful and hospitable.
Truly enjoyed the stay. Peter and his staff were extremely helpful and hospitable.
Rishi
Berkshires Untold
Berkshires UntoldLenox
10/10 Excellent
High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free.
There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...
High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free.
There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...
Jill
Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
10/10 Excellent
It was very conveniently located to the activities we were doing on our mini-vacation. There were a couple of issues that developed during our stay, but the staff did an excellent job of dealing with the issues.
It was very conveniently located to the activities we were doing on our mini-vacation. There were a couple of issues that developed during our stay, but the staff did an excellent job of dealing with the issues.
Elliott
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
- 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
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.