Winchester Vacation Rentals | Book Now, Save Up to 30%

All in pricing: Taxes and fees included

Save $1,178

House in Winchester, CT

Nov 16 - 21

$2,396/night

New

3 bedrooms

12 guests

$14,727$13,549total

Save $96

Preferred host

Entire cottage in Goshen, CT

Nov 16 - 19

$326/night

5.0

4

3 bedrooms

6 guests

$1,201$1,105total

Save $227

Preferred host

Cottage in Goshen, CT

Nov 30 - Dec 3

$602/night

5.0

1

3 bedrooms

6 guests

$2,279$2,052total

Save $101

Preferred host

Entire cabin in Cornwall, CT

Nov 23 - 26

$343/night

5.0

5

2 bedrooms

8 guests

$1,263$1,162total

Save $214

Guests rave

House in Cornwall, CT

Nov 16 - 19

$586/night

4.9

20

5 bedrooms

9 guests

$2,314$2,100total

Save $92

Preferred host

Entire home in Litchfield, CT

Dec 15 - 18

$312/night

5.0

6

3 bedrooms

7 guests

$1,151$1,059total

Save $111

Entire home in Avon, CT

Nov 16 - 19

$375/night

New

5 bedrooms

6 guests

$1,383$1,272total

Save $74

Preferred host

Entire home in Tolland, MA

Nov 16 - 19

$259/night

5.0

3

2 bedrooms

6 guests

$929$855total

Save $171

Preferred host

Entire home in Sheffield, MA

Dec 14 - 17

$346/night

5.0

3

5 bedrooms

10 guests

$1,313$1,143total

Save $65

Preferred host

House in Avon, CT

Dec 14 - 17

$175/night

4.7

53

2 bedrooms

5 guests

$661$596total

Save $194

Preferred host

House in Sheffield, MA

Nov 16 - 19

$576/night

5.0

10

4 bedrooms

14 guests

$2,107$1,912total

Save $195

House in New Marlborough, MA

Nov 16 - 19

$319/night

4.8

34

3 bedrooms

6 guests

$1,282$1,087total

Save $69

Cabin in New Marlborough, MA

Nov 16 - 19

$234/night

5.0

9

1 bedroom

2 guests

$868$798total

Save $566

House in New Marlborough, MA

Nov 16 - 19

$537/night

New

4 bedrooms

8 guests

$2,396$1,830total

Save $91

Preferred host

Entire cabin in New Marlborough, MA

Nov 23 - 26

$322/night

5.0

6

2 bedrooms

5 guests

$1,137$1,046total

Save $584

Condo in Farmington, CT

Dec 5 - Jan 6

$84/night

New

1 bedroom

2 guests

$3,267$2,683total

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Map shows last minute vacation rentals in Winchester