Holiday rentals near Winchester Historical Society
We found 380 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals within easy reach of Winchester Historical Society that can be your home away from home. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Winchester Historical Society
Showing deals for:7 Nov - 14 Nov
Image gallery for Peaceful, Post and Beam Loft, Sleeps 9
1010 out of 10 rating
Exceptional
(19 reviews)
Peaceful, Post and Beam Loft, Sleeps 9
Great Barrington, MA
14% off
Price is S$2,275
S$2,275
S$325 per night
includes taxes & fees
Image gallery for County Seat Colonial
1010 out of 10 rating
Exceptional
(11 reviews)
County Seat Colonial
Litchfield, CT
8% off
Price is S$3,861
S$3,861
S$552 per night
includes taxes & fees
Image gallery for Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Watertown, CT
8% off
Price is S$11,116
S$11,116
S$1,588 per night
includes taxes & fees
Image gallery for Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sandisfield, MA
8% off
Price is S$2,066
S$2,066
S$295 per night
includes taxes & fees
Image gallery for 5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
1010 out of 10 rating
Exceptional
(10 reviews)
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
New Marlborough, MA
16% off
Price is S$6,210
S$6,210
S$887 per night
includes taxes & fees
Image gallery for Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
1010 out of 10 rating
Exceptional
(15 reviews)
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Sheffield, MA
8% off
Price is S$5,532
S$5,532
S$790 per night
includes taxes & fees
Image gallery for Konkapot Cottage, Pastoral Bliss With Wide Views
1010 out of 10 rating
Exceptional
(20 reviews)
Konkapot Cottage, Pastoral Bliss With Wide Views
New Marlborough, MA
8% off
Price is S$3,190
S$3,190
S$456 per night
includes taxes & fees
Image gallery for Romantic and Secluded Berkshire's Gem
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Romantic and Secluded Berkshire's Gem
New Marlborough, MA
8% off
Price is S$6,331
S$6,331
S$904 per night
includes taxes & fees
Image gallery for Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
1010 out of 10 rating
Exceptional
(35 reviews)
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Plymouth, CT
8% off
Price is S$5,183
S$5,183
S$740 per night
includes taxes & fees
Image gallery for Beautiful retreat in a lake community to the enjoy the summer season.
1010 out of 10 rating
Exceptional
(40 reviews)
Beautiful retreat in a lake community to the enjoy the summer season.
Granville, MA
9% off
Price is S$2,167
S$2,167
S$310 per night
includes taxes & fees
Image gallery for Mountain View Getaway
1010 out of 10 rating
Exceptional
(55 reviews)
Mountain View Getaway
West Cornwall, CT
8% off
Price is S$2,802
S$2,802
S$400 per night
includes taxes & fees
Image gallery for Charming 1870 cape cottage in Litchfield
1010 out of 10 rating
Exceptional
(52 reviews)
Charming 1870 cape cottage in Litchfield
Litchfield, CT
8% off
Price is S$2,519
S$2,519
S$360 per night
includes taxes & fees
Image gallery for Forget-Me-Not by AvantStay | Bold Lakefront Escape
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Forget-Me-Not by AvantStay | Bold Lakefront Escape
Monterey, MA
9% off
Price is S$8,977
S$8,977
S$1,282 per night
includes taxes & fees
Image gallery for West Cornwall Cabin ~ 4 Mi to Covered Bridge!
9.69.6 out of 10 rating
Exceptional
(8 reviews)
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
West Cornwall, CT
7% off
Price is S$2,528
S$2,528
S$361 per night
includes taxes & fees
Image gallery for WINTER/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT
9.69.6 out of 10 rating
Exceptional
(17 reviews)
WINTER/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT
Monterey, MA
8% off
Price is S$5,337
S$5,337
S$762 per night
includes taxes & fees
Image gallery for Mountaintop Horse Farm with Heated Pool
1010 out of 10 rating
Exceptional
(31 reviews)
Mountaintop Horse Farm with Heated Pool
Bloomfield, CT
8% off
Price is S$2,931
S$2,931
S$419 per night
includes taxes & fees
Image gallery for Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Cornwall Bridge, CT
8% off
Price is S$7,050
S$7,050
S$1,007 per night
includes taxes & fees
Image gallery for Luxurious Mountain Retreat - Private 40-Acre Family Haven
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Luxurious Mountain Retreat - Private 40-Acre Family Haven
New Marlborough, MA
16% off
Price is S$7,367
S$7,367
S$1,052 per night
includes taxes & fees
Image gallery for Cozy Cabin in the Berkshires
1010 out of 10 rating
Exceptional
(17 reviews)
Cozy Cabin in the Berkshires
Sandisfield, MA
12% off
Price is S$2,415
S$2,415
S$345 per night
includes taxes & fees
Image gallery for Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views
9.69.6 out of 10 rating
Exceptional
(202 reviews)
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views
Salisbury, CT
12% off
Price is S$2,272
S$2,272
S$325 per night
includes taxes & fees
Image gallery for Private Island - Largest Fresh Water Reservoir in Mass....
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Private Island - Largest Fresh Water Reservoir in Mass....
Otis, MA
16% off
Price is S$4,238
S$4,238
S$605 per night
includes taxes & fees
Image gallery for Charming apartment 7 minute walk to downtown
1010 out of 10 rating
Exceptional
(15 reviews)
Charming apartment 7 minute walk to downtown
Torrington, CT
8% off
Price is S$1,724
S$1,724
S$246 per night
includes taxes & fees
Image gallery for Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
1010 out of 10 rating
Exceptional
(5 reviews)
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Harwinton, CT
15% off
Price is S$1,892
S$1,892
S$270 per night
includes taxes & fees
Image gallery for Peaceful Meadow Retreat
1010 out of 10 rating
Exceptional
(9 reviews)
Peaceful Meadow Retreat
Granby, CT
10% off
Price is S$1,340
S$1,340
S$191 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winchester Historical Society
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Sleeps 6 · 1 bedroom · 1 bathroom
8.88.8 out of 10
Excellentexcellent
20 reviews(20 reviews)
Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
Waterfront Lake Home on Tranquil Harwinton Lake with spectacular 180⁰ view.
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
188 reviews(188 reviews)
Amazing 11 Bedroom 15 Bathroom Mansion Close to Beaches
Sleeps 24 · 11 bedrooms · 11+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
10 reviews(10 reviews)
Stunning Retreat on 62 Acres, 7000 sq ft, Pool and Hot Tub
Sleeps 12 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Cozy 2-bedroom Cottage with Access to Bantam Lake
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Top rated rentals - Winchester Historical Society
Incredible stay
1010 out of 10
Exceptionalexceptional
72 reviews(72 reviews)
Phenomenal
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value