COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Holiday Houses in Pittsfield

Updating

age 0-16
162 Results

Relevance

Price low to high

Price high to low

Reviews

162 Holiday homes

Charming condo w/ shared hot tub - near golf, ski trails & fishing!

Pittsfield house

2 bedrooms / 1 bathroom / sleeps 6

from £143 / night

£996 / week

Colonial home with a yard & deck, close to golf & skiing!

Pittsfield house

5 bedrooms / 3 bathrooms / sleeps 13

from £284 / night

£1,986 / week

Killington area ski house

Pittsfield house

5 bedrooms / 2 bathrooms / sleeps 11

2

Responds fast! avg. 3 hours 20 minutes

from £322 / night

£2,255 / week

Killington area mountain home on 60 acres and surrounded by National Forests

Pittsfield house

4 bedrooms / 2 bathrooms / sleeps 9

2

Responds fast! avg. 2 hours 17 minutes

from £172 / night

£1,202 / week

Sweet Life

Pittsfield house

3 bedrooms / 2 bathrooms / sleeps 12

1

Responds fast! avg. 3 hours 54 minutes

from £305 / night

£2,130 / week

Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail

Pittsfield house

3 bedrooms / 1 bathroom / sleeps 6

from £119 / night

£828 / week

Silver Spring Chalet

Pittsfield house

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 3 hours 54 minutes

from £305 / night

£2,130 / week

Escape

Pittsfield house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 54 minutes

from £437 / night

£3,054 / week

Great rentals within 20 miles that match your search

Minutes from Killington + Okemo + Woodstock, VT come and experience The Cabin

Bridgewater log cabin

4 bedrooms / 3 bathrooms / sleeps 24

from £752 / night

£5,262 / week

☆ SKI ON & OFF! ☆ Luxury Trailside Condo! NEW Steam Shower, Hot Tub, Pool

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

5

Responds fast! avg. 12 minutes

from £141 / night

£987 / week

RV/Camper rental Randolph VT area

Braintree camper van

2 bedrooms / 2 bathrooms / sleeps 6

from £118 / night

£706 / week

Organic Farm, House, Barn Event Rental

Hancock farmhouse

10 bedrooms / 4 bathrooms / sleeps 20

from £895 / night

£3,295 - £6,721 / week

Ski Killington Vermont

Killington apartment

1 bedroom / 2 bathrooms / sleeps 6

from £179 / night

£1,224 / week

Killington Vermont- 2 Bedroom/1Bath. Right in the heart of Ski country!

Killington house

2 bedrooms / 1 bathroom / sleeps 8

from £236 / night

£1,647 / week

Vermont Living Central Location

Rutland apartment

2 bedrooms / 2 bathrooms / sleeps 4

from £236 / night

£1,412 / week

Mountain Green WLK 2 LIFT/Access RD. Kilington VT

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

1

from £165 / night

£1,153 / week

Hidden House Vermont : Private Mountain Retreat in the Heart of The Green Mts.

Bethel apartment

3 bedrooms / 1 bathroom / sleeps 4

from £217 / night

£1,516 / week

Vermont Farmhouse

Granville house

3 bedrooms / 2 bathrooms / sleeps 6

from £236 / night

£1,412 / week

Serenity at Sunrise

Killington hotel apartment

3 bedrooms / 3 bathrooms / sleeps 6

1

from £236 / night

£1,506 - £4,706 / week

3 bedroom 2 bath Pinnacle Condo at Killington

Killington apartment

3 bedrooms / 2 bathrooms / sleeps 8

3

from £518 / night

£2,636 / week

Modern Country in Vermont

Rutland apartment

1 bedroom / 1 bathroom / sleeps 2

from £165 / night

£942 / week

ROSE'S COZY MOUNTAINVIEW - A -

Rutland townhouse

2 bedrooms / 1 bathroom / sleeps 5

from £162 / night

£809 / week

HOMESHARE at ROSE'S COZY MOUNTAINVIEW Duplex

Rutland house

1 bedroom / 1 bathroom / sleeps 3

from £51 / night

£325 - £455 / week

Private Green Mountain get-away with pond

Ripton house

3 bedrooms / 2 bathrooms / sleeps 6

from £372 / night

£2,601 / week

Ski House Between Killington and Okemo

Plymouth condo

4 bedrooms / 2 bathrooms / sleeps 8

from £176 / night

£1,230 / week

Sun House Studios

Sharon house

3 bedrooms / 2 bathrooms / sleeps 6

9

Responds fast! avg. 1 hour 57 minutes

from £89 / night

£533 - £1,154 / week

Contemporary Spacious 7br/6.5 bath home near Killington VT

Mendon house

7 bedrooms / 7 bathrooms / sleeps 22

from £700 / night

£1,400 / week

ROSE'S COZY MOUNTAINVIEW - B -

Rutland house

2 bedrooms / 2 bathrooms / sleeps 7

from £139 / night

£913 / week

Spectacular Water Views From Every Room ~ Directly On Lake Hortonia, Vt.

Brandon house

3 bedrooms / 2 bathrooms / sleeps 6

from £189 / night

£1,316 / week

2 bedroom premium AAA rated condo across from the slopes-2C4

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

from £170 / night

£858 - £2,773 / week

2 bedroom premium AAA rated condo across from the slopes-2D2

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

from £170 / night

£858 - £2,773 / week

Premier Ski-in / Ski-out - 3 Bed, Sunrise Mountain

Killington apartment

3 bedrooms / 2 bathrooms / sleeps 8

from £579 / night

£4,052 / week

Heavenly Vacation Home on Silver Lake

Barnard house

5 bedrooms / 3 bathrooms / sleeps 7

13

from £439 / night

£3,067 / week

Cozy Apt Near Killington Ski Area & Sugarbush Farm

Bridgewater apartment

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 20 minutes

from £137 / night

£956 / week

Hideaway Chalet Comfort for 24 SKI PASSES 50% ski slopes 2min HOT TUB

Killington house

8 bedrooms / 6 bathrooms / sleeps 24

1

Responds fast! avg. 1 hour 56 minutes

from £855 / night

£1,566 / week

Cricket Hill - Cozy, clean, private, spacious. 5 rooms. Entire lower level.

Killington house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 58 minutes

from £120 / night

£838 / week

Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!

Killington house

6 bedrooms / 3 bathrooms / sleeps 12

from £485 / night

£3,394 / week

Cozy Condo w/ Pool Access Near Killington Resort!

Killington apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 11 minutes

from £136 / night

£951 / week

Plymouth Home w/ Jacuzzi Near Okemo & Killington!

Plymouth house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 15 minutes

from £324 / night

£2,267 / week

ROSE'S COZY MOUNTAINVIEW -A & -B-

Mendon house

4 bedrooms / 3 bathrooms / sleeps 12

from £420 / night

£1,381 / week

Viewing 40 of 162
rentals in Pittsfield