Holiday rentals near Winchester Historical Society
We found 383 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:17 Oct - 24 Oct
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, Massachusetts
14% off
Price is NZ$3,129
NZ$3,129
NZ$447 per night
includes taxes & fees
Image gallery for Sweetbrier Farm -- Gorgeous Views, Beautiful Home
1010 out of 10 rating
Exceptional
(29 reviews)
Sweetbrier Farm -- Gorgeous Views, Beautiful Home
Litchfield, CT
12% off
Price is NZ$8,617
NZ$8,617
NZ$1,231 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 NZ$8,197
NZ$8,197
NZ$1,171 per night
includes taxes & fees
Image gallery for The Country Retreat House
1010 out of 10 rating
Exceptional
(6 reviews)
The Country Retreat House
Lakeville, CT
8% off
Price is NZ$9,753
NZ$9,753
NZ$1,393 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 NZ$4,165
NZ$4,165
NZ$595 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
(39 reviews)
Beautiful retreat in a lake community to the enjoy the summer season.
Granville, MA
9% off
Price is NZ$2,860
NZ$2,860
NZ$409 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
(17 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sandisfield, MA
8% off
Price is NZ$2,448
NZ$2,448
NZ$350 per night
includes taxes & fees
Image gallery for Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
1010 out of 10 rating
Exceptional
(33 reviews)
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Plymouth, CT
8% off
Price is NZ$5,603
NZ$5,603
NZ$800 per night
includes taxes & fees
Image gallery for Mountain View Getaway
1010 out of 10 rating
Exceptional
(54 reviews)
Mountain View Getaway
West Cornwall, CT
8% off
Price is NZ$3,766
NZ$3,766
NZ$538 per night
includes taxes & fees
Image gallery for Charming 1870 cape cottage in Litchfield
1010 out of 10 rating
Exceptional
(51 reviews)
Charming 1870 cape cottage in Litchfield
Litchfield, CT
8% off
Price is NZ$3,291
NZ$3,291
NZ$470 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 NZ$9,243
NZ$9,243
NZ$1,320 per night
includes taxes & fees
Image gallery for Mountaintop Horse Farm with Heated Pool
1010 out of 10 rating
Exceptional
(29 reviews)
Mountaintop Horse Farm with Heated Pool
Bloomfield, CT
8% off
Price is NZ$3,825
NZ$3,825
NZ$546 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 NZ$9,646
NZ$9,646
NZ$1,378 per night
includes taxes & fees
Image gallery for Waterfront oasis in heart of Berkshires
1010 out of 10 rating
Exceptional
(17 reviews)
Waterfront oasis in heart of Berkshires
Sandisfield, MA
8% off
Price is NZ$7,656
NZ$7,656
NZ$1,094 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 NZ$3,154
NZ$3,154
NZ$451 per night
includes taxes & fees
Image gallery for The Blue Elm - A Historic Berkshire Cottage
1010 out of 10 rating
Exceptional
(7 reviews)
The Blue Elm - A Historic Berkshire Cottage
Ashley Falls, MA
8% off
Price is NZ$2,845
NZ$2,845
NZ$406 per night
includes taxes & fees
Image gallery for Newly renovated charming home , Brand new chefs kitchen very comfortable home .
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Newly renovated charming home , Brand new chefs kitchen very comfortable home .
Lakeville, CT
12% off
Price is NZ$4,924
NZ$4,924
NZ$703 per night
includes taxes & fees
Image gallery for Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Avon, CT
8% off
Price is NZ$3,947
NZ$3,947
NZ$564 per night
includes taxes & fees
Image gallery for Converted Berkshire schoolhouse on a quiet river
1010 out of 10 rating
Exceptional
(32 reviews)
Converted Berkshire schoolhouse on a quiet river
Great Barrington, MA
8% off
Price is NZ$3,648
NZ$3,648
NZ$521 per night
includes taxes & fees
Image gallery for Cozy Lakefront Bungalow w firepit/dock/kayaks
1010 out of 10 rating
Exceptional
(29 reviews)
Cozy Lakefront Bungalow w firepit/dock/kayaks
Plymouth, CT
8% off
Price is NZ$6,699
NZ$6,699
NZ$957 per night
includes taxes & fees
Image gallery for Lakefront Tranquility/Fishermans Delight
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Lakefront Tranquility/Fishermans Delight
New Hartford, CT
8% off
Price is NZ$3,499
NZ$3,499
NZ$500 per night
includes taxes & fees
Image gallery for ISLAND WATERFRONT Sleeps up to 8
9.09.0 out of 10 rating
Wonderful
(73 reviews)
ISLAND WATERFRONT Sleeps up to 8
Southwick, MA
8% off
Price is NZ$3,286
NZ$3,286
NZ$469 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 NZ$1,743
NZ$1,743
NZ$249 per night
includes taxes & fees
Image gallery for Secluded retreat, 13 acres, solar, pool, river views, pet & child friendly
9.29.2 out of 10 rating
Wonderful
(116 reviews)
Secluded retreat, 13 acres, solar, pool, river views, pet & child friendly
Cornwall Bridge, CT
8% off
Price is NZ$7,578
NZ$7,578
NZ$1,083 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
Villa
Chalet
Find the best place to stay - Winchester Historical Society
Showing deals for: 13 Oct - 16 Oct
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)
The current price is NZ$1,417
NZ$1,417
for 3 nights, 1 cabin
NZ$472 per night
includes taxes & fees
Waterfront Lake Home on Tranquil Harwinton Lake with spectacular 180⁰ view.
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
184 reviews(184 reviews)
The current price is NZ$2,020
NZ$2,020
for 3 nights, 1 cottage
NZ$673 per night
includes taxes & fees
Amazing 11 Bedroom 15 Bathroom Mansion Close to Beaches
Sleeps 24 · 11 bedrooms · 11+ bathrooms
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
The current price is NZ$7,038
NZ$7,038
for 3 nights, 1 home
NZ$2,346 per night
includes taxes & fees
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)
The current price is NZ$9,510
NZ$9,510
for 3 nights, 1 home
NZ$3,170 per night
includes taxes & fees
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
67 reviews(67 reviews)
The current price is NZ$1,456
NZ$1,456
for 3 nights, 1 cottage
NZ$485 per night
includes taxes & fees
Postcard Cabins Machimoodus
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
35 reviews(35 reviews)
The current price is NZ$1,444
NZ$1,444
for 3 nights, 1 cabin
NZ$481 per night
includes taxes & fees
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