Holiday rentals near Connecticut Railroad Historical Museum
We found 667 holiday rentals — enter your dates for availability
Choose the right private holiday rental within easy reach of Connecticut Railroad Historical Museum. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a fireplace. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Connecticut Railroad Historical Museum
Showing deals for:19 Sept - 26 Sept
Image gallery for 5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
1010 out of 10 rating
Exceptional
(9 reviews)
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
New Marlborough, MA
12% off
Price is AU$6,905
AU$6,905
AU$986 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
(9 reviews)
Newly renovated charming home , Brand new chefs kitchen very comfortable home .
Lakeville, CT
12% off
Price is AU$4,401
AU$4,401
AU$629 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 AU$3,336
AU$3,336
AU$477 per night
includes taxes & fees
Image gallery for Cozy Cottage on the Lake
9.49.4 out of 10 rating
Exceptional
(26 reviews)
Cozy Cottage on the Lake
Otis, MA
7% off
Price is AU$3,115
AU$3,115
AU$445 per night
includes taxes & fees
Image gallery for Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
1010 out of 10 rating
Exceptional
(63 reviews)
Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
Great Barrington, MA
8% off
Price is AU$7,665
AU$7,665
AU$1,095 per night
includes taxes & fees
Image gallery for Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Great Barrington, MA
6% off
Price is AU$7,299
AU$7,299
AU$1,043 per night
includes taxes & fees
Image gallery for Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount
1010 out of 10 rating
Exceptional
(10 reviews)
Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount
Hillsdale, NY
8% off
Price is AU$8,194
AU$8,194
AU$1,171 per night
includes taxes & fees
Image gallery for Gorgeous Sheffield Home in Heart of Berkshires
1010 out of 10 rating
Exceptional
(50 reviews)
Gorgeous Sheffield Home in Heart of Berkshires
Sheffield, MA
8% off
Price is AU$8,430
AU$8,430
AU$1,204 per night
includes taxes & fees
Image gallery for COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
9.89.8 out of 10 rating
Exceptional
(159 reviews)
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
Lee, MA
12% off
Price is AU$2,584
AU$2,584
AU$369 per night
includes taxes & fees
Image gallery for Elegant Modern Farmhouse with Pool and Gardens, steps from Nature Preserve
1010 out of 10 rating
Exceptional
(15 reviews)
Elegant Modern Farmhouse with Pool and Gardens, steps from Nature Preserve
Sharon, CT
8% off
Price is AU$10,529
AU$10,529
AU$1,504 per night
includes taxes & fees
Image gallery for Berkshire Lake at the Pillow, and EV!
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Berkshire Lake at the Pillow, and EV!
Lee, MA
8% off
Price is AU$4,517
AU$4,517
AU$645 per night
includes taxes & fees
Image gallery for Cozy Log Cabin Retreat with Pool on 4 Acres
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Cozy Log Cabin Retreat with Pool on 4 Acres
Canaan, CT
7% off
Price is AU$3,921
AU$3,921
AU$560 per night
includes taxes & fees
Image gallery for Cozy Cabin in the Berkshires
1010 out of 10 rating
Exceptional
(16 reviews)
Cozy Cabin in the Berkshires
Sandisfield, MA
12% off
Price is AU$2,882
AU$2,882
AU$412 per night
includes taxes & fees
Image gallery for Ashintully Cottage in spectacular setting
1010 out of 10 rating
Exceptional
(33 reviews)
Ashintully Cottage in spectacular setting
Lee, MA
17% off
Price is AU$3,772
AU$3,772
AU$539 per night
includes taxes & fees
Image gallery for Stay at Beaver Lodge!
1010 out of 10 rating
Exceptional
(29 reviews)
Stay at Beaver Lodge!
Monterey, MA
8% off
Price is AU$2,167
AU$2,167
AU$310 per night
includes taxes & fees
Image gallery for Secluded Family Home in Serene Stockbridge Woods
1010 out of 10 rating
Exceptional
(21 reviews)
Secluded Family Home in Serene Stockbridge Woods
South Lee, MA
8% off
Price is AU$6,171
AU$6,171
AU$882 per night
includes taxes & fees
Image gallery for Salisbury Cottage Retreat
1010 out of 10 rating
Exceptional
(11 reviews)
Salisbury Cottage Retreat
Salisbury, CT
16% off
Price is AU$2,828
AU$2,828
AU$404 per night
includes taxes & fees
Image gallery for TREEMENDOUS VIEWS COTTAGE
1010 out of 10 rating
Exceptional
(21 reviews)
TREEMENDOUS VIEWS COTTAGE
Amenia, NY
19% off
Price is AU$4,209
AU$4,209
AU$601 per night
includes taxes & fees
Image gallery for Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
1010 out of 10 rating
Exceptional
(49 reviews)
Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
Great Barrington, MA
8% off
Price is AU$20,378
AU$20,378
AU$2,911 per night
includes taxes & fees
Image gallery for Classic Stockbridge Cottage
1010 out of 10 rating
Exceptional
(15 reviews)
Classic Stockbridge Cottage
Stockbridge, Massachusetts
14% off
Price is AU$4,462
AU$4,462
AU$637 per night
includes taxes & fees
Image gallery for Two Rooms with En-Suite in Quiet Woodland
1010 out of 10 rating
Exceptional
(30 reviews)
Two Rooms with En-Suite in Quiet Woodland
Hillsdale, NY
8% off
Price is AU$2,746
AU$2,746
AU$392 per night
includes taxes & fees
Image gallery for Doodletown Cabin: Pond—Outdoor Dining—Games Barn!
9.69.6 out of 10 rating
Exceptional
(65 reviews)
Doodletown Cabin: Pond—Outdoor Dining—Games Barn!
Ancram, NY
12% off
Price is AU$6,839
AU$6,839
AU$977 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 AU$8,802
AU$8,802
AU$1,257 per night
includes taxes & fees
Image gallery for Forget-Me-Not by AvantStay | Bold Lakefront Escape
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Forget-Me-Not by AvantStay | Bold Lakefront Escape
Monterey, Massachusetts
10% off
Price is AU$12,453
AU$12,453
AU$1,779 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Connecticut Railroad Historical Museum
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
Sleeps 5 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
159 reviews(159 reviews)
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Sleeps 20 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
231 reviews(231 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Villa with Access to Amazing Amenities!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
125 reviews(125 reviews)
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Sleeps 10 · 4 bedrooms · 2 bathrooms
7.27.2 out of 10
Goodgood
44 reviews(44 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