Houses in Pittsfield and Chalets – Holiday Lettings - Holiday Rentals Pittsfield

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290 Holiday homes

(1) Excellent 

16

Holiday home rental

Vermont / Pittsfield

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Child friendly

from £307 / night

£1,531 / week

Book View

from £307 / night

(2) Very Good 

27

Home rental in Pittsfield

Vermont / Pittsfield

4 9 2 nights min

  • 4 bedrooms
  • sleeps 9
  • 2 nights min
  • Child friendly

from £115 / night

£460 - £2,067 / week

Book View

Responds fast!
avg. 3 hours 43 minutes

from £115 / night

(1)  

26

Holiday home in Pittsfield

Vermont / Pittsfield

3 12 min stay varies

  • 3 bedrooms
  • sleeps 12
  • min stay varies
  • Child friendly
  • Pet friendly

from £201 / night

£1,404 / week

Book View

Responds fast!
avg. 36 minutes

from £201 / night

25

Holiday home in Pittsfield

Vermont / Pittsfield

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly

from £56 / night

£391 / week

Book View

from £56 / night

26

Home rental in Pittsfield

Vermont / Pittsfield

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Pet friendly

from £173 / night

£536 - £1,665 / week

Book View

from £173 / night

24

Holiday chalet with golf nearby in Pittsfield

Vermont / Pittsfield

3 20 min stay varies

  • 3 bedrooms
  • sleeps 20
  • min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from £227 / night

£1,589 - £6,361 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £227 / night

Great rentals within 20 miles that match your search

Distance approx 17.38 miles from Pittsfield

16

Holiday hotel apartment in Woodstock

Vermont / Woodstock

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £192 / night

£1,148 / week

Book View

from £192 / night

Distance approx 9.98 miles from Pittsfield

(4) Excellent 

8

Holiday log cabin in Barnard

Vermont / Barnard

2 min stay varies

  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km

from £85 / night

£499 - £687 / week

Book View

from £85 / night

Distance approx 17.59 miles from Pittsfield

25

Home accommodation in Plymouth

Vermont / Plymouth

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 1 km
  • Child friendly
  • Pet friendly

from £269 / night

£1,841 / week

Book View

from £269 / night

Distance approx 18.16 miles from Pittsfield

16

Holiday home in Plymouth

Vermont / Plymouth

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £169 / night

£959 / week

Book View

from £169 / night

Distance approx 13.55 miles from Pittsfield

(5) Excellent 

27

Holiday cottage in Brandon

Vermont / Brandon

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 1 km
  • Air conditioning
  • Private garden

from £92 / night

£533 - £901 / week

Book View

Responds fast!
avg. 27 minutes

from £92 / night

Distance approx 12.18 miles from Pittsfield

(9) Excellent 

26

Rutland holiday home accommodation

Vermont / Rutland

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Nearest beach 8 km
  • Child friendly
  • Private garden

from £42 / night

£269 - £376 / week

Book View

from £42 / night

Distance approx 12.99 miles from Pittsfield

32

Holiday home in Ripton

Vermont / Ripton

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden

from £307 / night

£2,147 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £307 / night

Distance approx 13.92 miles from Pittsfield

13

Ski apartment to rent in Rutland

Vermont / Rutland

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Ski
  • Child friendly

from £192 / night

£1,151 / week

Book View

from £192 / night

Distance approx 12.04 miles from Pittsfield

(1) Excellent 

25

Ski hotel apartment to rent in Killington

Vermont / Killington

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child friendly

from £180 / night

£1,262 - £1,989 / week

Book View

Responds fast!
avg. 3 hours 26 minutes

from £180 / night

Distance approx 13.92 miles from Pittsfield

9

Rutland ski apartment to rent.

Vermont / Rutland

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Ski

from £134 / night

£765 / week

Book View

from £134 / night

Distance approx 10.06 miles from Pittsfield

24

Holiday condo with shared pool in Killington

Vermont / Killington

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly

from £223 / night

£618 - £2,435 / week

Book View

from £223 / night

Distance approx 10.07 miles from Pittsfield

15

Killington ski condo to rent.

Vermont / Killington

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ski
  • Child friendly

from £192 / night

£1,342 / week

Book View

Responds fast!
avg. 54 minutes

from £192 / night

Distance approx 7.52 miles from Pittsfield

38

Holiday condo with shared pool in Killington

Vermont / Killington

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly

from £96 / night

£671 / week

Book View

from £96 / night

Distance approx 10.39 miles from Pittsfield

4

Home rental in Killington

Vermont / Killington

5 12 3 nights min

  • 5 bedrooms
  • sleeps 12
  • 3 nights min
  • Child friendly
  • Private garden

from £381 / night

£2,664 / week

Book View

Responds fast!
avg. 2 hours 37 minutes

from £381 / night

Distance approx 7.88 miles from Pittsfield

20

Holiday home in Killington

Vermont / Killington

8 24 min stay varies

  • 8 bedrooms
  • sleeps 24
  • min stay varies
  • Child friendly
  • Private garden

from £614 / night

£4,295 / week

Book View

from £614 / night

Distance approx 7.22 miles from Pittsfield

17

Ski condo to rent in Killington

Vermont / Killington

2 9 2 nights min

  • 2 bedrooms
  • sleeps 9
  • 2 nights min
  • Swimming pool
  • Ski
  • Child friendly

from £169 / night

£1,181 / week

Book View

from £169 / night

Distance approx 8.16 miles from Pittsfield

(8) Excellent 

18

Killington holiday home rental

Vermont / Killington

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £460 / night

£2,684 - £4,218 / week

Book View

Responds fast!
avg. 1 hour 18 minutes

from £460 / night

Distance approx 12.13 miles from Pittsfield

25

Holiday home in Mendon

Vermont / Mendon

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 30 km
  • Child friendly
  • Private garden

from £249 / night

£1,067 / week

Book View

from £249 / night

Distance approx 9.75 miles from Pittsfield

28

Holiday condo with shared pool in Killington

Vermont / Killington

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly

from £92 / night

£590 / week

Book View

Responds fast!
avg. 2 hours 4 minutes

from £92 / night

Distance approx 8.02 miles from Pittsfield

6

Holiday apartment in Killington

Vermont / Killington

2 3 3 nights min

  • 2 bedrooms
  • sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children

from £115 / night

£863 - £1,131 / week

Book View

from £115 / night

Distance approx 9.75 miles from Pittsfield

24

Holiday apartment with shared pool, golf nearby in Killington

Vermont / Killington

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £109 / night

£763 - £3,989 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £109 / night

Distance approx 12.07 miles from Pittsfield

24

Holiday home with shared pool, golf nearby in Killington

Vermont / Killington

3 12 min stay varies

  • 3 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Car not necessary
  • Pet friendly

from £182 / night

£1,273 - £7,096 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £182 / night

Distance approx 10.23 miles from Pittsfield

25

Holiday home in Barnard

Vermont / Barnard

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Private garden

from £227 / night

£1,500 / week

Book View

from £227 / night

Distance approx 16.17 miles from Pittsfield

15

Holiday home in Granville

Vermont / Granville

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly

from £192 / night

£1,151 / week

Book View

from £192 / night

Distance approx 9.75 miles from Pittsfield

24

Holiday apartment with shared pool, golf nearby in Killington

Vermont / Killington

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £92 / night

£639 - £3,275 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £92 / night

Distance approx 7.08 miles from Pittsfield

23

Ski home to rent in Killington

Vermont / Killington

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Ski
  • Child friendly
  • Private garden

from £345 / night

£2,416 / week

Book View

from £345 / night

Distance approx 9.75 miles from Pittsfield

4

Holiday apartment with shared pool, golf nearby in Killington

Vermont / Killington

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £109 / night

£763 - £4,032 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £109 / night

Distance approx 9.71 miles from Pittsfield

24

Holiday apartment with shared pool, golf nearby in Killington

Vermont / Killington

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £92 / night

£639 - £3,098 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £92 / night

Distance approx 19.68 miles from Pittsfield

24

Holiday home with golf nearby in Plymouth

Vermont / Plymouth

4 11 min stay varies

  • 4 bedrooms
  • sleeps 11
  • min stay varies
  • Child friendly
  • Car not necessary

from £352 / night

£2,464 - £4,547 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £352 / night

Distance approx 9.76 miles from Pittsfield

24

Holiday condo with shared pool, golf nearby in Killington

Vermont / Killington

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £92 / night

£639 - £2,545 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £92 / night

Distance approx 2.94 miles from Pittsfield

16

Holiday home with golf nearby in Stockbridge

Vermont / Stockbridge

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child friendly
  • Car not necessary

from £250 / night

£1,746 - £7,249 / week

Book View

Responds fast!
avg. 1 hour 56 minutes

from £250 / night

Distance approx 6.81 miles from Pittsfield

15

Home rental in Killington

Vermont / Killington

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from £273 / night

£1,911 - £7,633 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £273 / night

Distance approx 7.67 miles from Pittsfield

24

Holiday home in Killington

Vermont / Killington

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

from £339 / night

£2,040 - £4,391 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £339 / night

Distance approx 7.7 miles from Pittsfield

21

Holiday apartment with shared pool, golf nearby in Killington

Vermont / Killington

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £109 / night

£763 - £4,085 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £109 / night