Find Romantic Hotels in Southfield, MA

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Check availability on Southfield Romantic Hotels

Our top choices for Southfield romantic hotels

Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
The price is NT$4,658
NT$6,600 total
includes taxes & fees
Jan 12 - 2026/1/13
The Red Lion Inn
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (270)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is NT$6,429
NT$7,394 total
includes taxes & fees
Dec 21 - Dec 22
Interlaken Inn & Resort
Library
Blackberry River Inn

Blackberry River 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
The price is NT$5,127
NT$5,896 total
includes taxes & fees
Dec 17 - Dec 18
Blackberry River Inn
Exterior
The Millerton Inn

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.0 out of 10, Very Good, (9)
"Beautiful property, only stayed one night for business but it was very nice. Great burger at the restaurant downstairs! Possibly one of the best burgers I’ve ever had!"
United States
Jason
The price is NT$5,028
NT$5,688 total
includes taxes & fees
Jan 1 - 2026/1/2
The Millerton Inn
Room (King Room) | Iron/ironing board, free WiFi, bed sheets
Gateways Inn & Restaurant

Gateways Inn & Restaurant

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
The price is NT$4,792
NT$5,592 total
includes taxes & fees
Jan 4 - 2026/1/5
Gateways Inn & Restaurant
Front of property
Gedney Farm

Gedney Farm

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
The price is NT$5,786
NT$6,347 total
includes taxes & fees
Dec 14 - Dec 15
Gedney Farm
Business center
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 Chesterwood

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
The price is NT$11,914
NT$14,412 total
includes taxes & fees
Jan 5 - 2026/1/6
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164)
"Everything was perfect - location and accommodation."
United States
Christopher
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.
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Top Southfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The best of the best A definite destination and accommodations"
Seth 1-night trip
Posted 5 days ago
The Red Lion Inn
The Ponds at Foxhollow

The Ponds at Foxhollow

10/10 Excellent
"There was a coffee machine but no filters nor beans. I wish they had been provided."
art 3-night trip
Posted 11 days ago
The Ponds at Foxhollow

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Frequently asked questions

Searching for romantic hotels in Southfield?
If you and your partner need a romantic escape, we've got just the thing. If you want to explore the area, you might head to Umpachene Falls Park, Campbell Falls State Park, or Suter Farm. If you're interested in staying near a certain attraction, you can sort properties by neighborhood or distance 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 Southfield?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Southfield: 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 Southfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Southfield?
There's nothing better than experiencing a new place with your sweetheart, so consider taking time to discover all there is to see and do in Southfield. You might think about stopping by Umpachene Falls Park, Campbell Falls State Park, or Suter Farm while you're seeing the sights.
What's the best way to get to Southfield and around town during my romantic getaway?
These transportation options in Southfield might help your romantic trip go off without a hitch: To get to Southfield, you can fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest major airport, located 22.6 mi (36.3 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.