Stockbridge Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

219 Houses

(2) Excellent 

39

Hawks View Chalet

Vermont / Stockbridge

Stockbridge house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly

Price per night from

$330

Responds fast!
avg. 1 hour 30 minutes

Price per night from

$330

32

Cedar Rock Chalet

Vermont / Stockbridge

Stockbridge house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$203

Responds fast!
avg. 1 hour 30 minutes

Price per night from

$203

33

NEW! 4-Season Stockbridge Home-Fireplace & Deck!

Vermont / Stockbridge

Stockbridge house

6 16 min stay varies

  • 6 bedrooms
  • sleeps 16
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$365

Responds fast!
avg. 9 minutes

Price per night from

$365

16

Hawks View Chalet

Vermont / Stockbridge

Stockbridge house

4 10 min stay varies

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

Price per night from

$437

Responds fast!
avg. 3 hours 56 minutes

Price per night from

$437

5

Cedar Rock Chalet

Vermont / Stockbridge

Stockbridge chalet

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Car not necessary
  • Pet Friendly

Price per night from

$280

Responds fast!
avg. 3 hours 56 minutes

Price per night from

$280

Great rentals within 20 miles that match your search

Distance approx 15.57 km from Stockbridge

(9) Excellent 

30

Sun House Studios

Vermont / Sharon

Sharon house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Ask about pets
  • Private garden
“Above expectations and perfect location for visiting Vermont Law School.” Perfect location for visiting Vermont Law School. Comfortable and all amenities that would be needed are provided. Clean and great attention to detail. Would return now that
…see more

Price per night from

$172

Responds fast!
avg. 1 hour 24 minutes

Price per night from

$172

Distance approx 8.46 km from Stockbridge

28

Killington Ski-In/Ski-Out Townhouse w/ Mtn. Views!

Vermont / Killington

Killington house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$171

Responds fast!
avg. 22 minutes

Price per night from

$171

Distance approx 10.6 km from Stockbridge

15

Ski right home! Updated 1br condo, fireplace, pool, hot tub, fitness center.

Vermont / Killington

Killington condo

1 4 min stay varies

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

Price per night from

$286

Responds fast!
avg. 2 hours 58 minutes

Price per night from

$286

Distance approx 12.39 km from Stockbridge

28

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

Vermont / Killington

Killington apartment

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$743

Price per night from

$743

Distance approx 14.55 km from Stockbridge

(5) Excellent 

27

The Little House Vermont

Vermont / Brandon

Brandon cottage

1 4 min stay varies

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

Price per night from

$136

Responds fast!
avg. 34 minutes

Price per night from

$136

Distance approx 8.27 km from Stockbridge

39

Quaint, dog-friendly condo with resort pool and hot tub, close to skiing!

Vermont / Killington

Killington house

2 6 min stay varies

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

Price per night from

$125

Price per night from

$125

Distance approx 10.99 km from Stockbridge

4

Ski Killington, Pico, Snow Mobile, Summer Fun

Vermont / Killington

Killington house

5 12 3 nights min

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

Price per night from

$571

Responds fast!
avg. 2 hours 10 minutes

Price per night from

$571

Distance approx 16.12 km from Stockbridge

(6) Excellent 

27

Woodstock Carriage House! Vermont's finest county road with homes and farms.

Vermont / Woodstock

Woodstock house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$252

Price per night from

$252

Distance approx 12.53 km from Stockbridge

(1) Excellent 

25

Serenity at Sunrise

Vermont / Killington

Killington hotel apartment

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$430

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$430

Distance approx 8.63 km from Stockbridge

(8) Excellent 

18

Killington Mountain Slopeside Home

Vermont / Killington

Killington house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary
“Ski home at Killington” We've been here for 10 days in late January. Wonderful place. Excellent home. We were two families with 4 aDT, CHD 4 with 6.9, 11 and 14 years. We left and came back home from skiing. We used the heated pool at the sport cente
…see more

Price per night from

$686

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$686

Distance approx 15.08 km from Stockbridge

9

Modern Country in Vermont

Vermont / Rutland

Rutland apartment

1 2 2 nights min

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

Price per night from

$200

Price per night from

$200

Distance approx 12.65 km from Stockbridge

(3) Very Good 

19

Colonial-style solid-timber home in a quiet setting; sanctuary.

Vermont / Barnard

Barnard house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 8 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$262

Price per night from

$262

Distance approx 10.31 km from Stockbridge

28

Mountain Green Recently Updated 1 BR Condo Across The Street From Snowshed Lodge

Vermont / Killington

Killington condo

1 4 2 nights min

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

Price per night from

$246

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$246

Distance approx 10.1 km from Stockbridge

23

Organic Farm, House, Barn Event Rental

Vermont / Hancock

Hancock farmhouse

10 20 2 nights min

  • 10 bedrooms
  • sleeps 20
  • 2 nights min
  • Ski
  • Child Friendly

Price per night from

$1,085

Price per night from

$1,085

Distance approx 12.56 km from Stockbridge

24

Sunrise - Timberline L-1

Vermont / Killington

Killington house

3 12 min stay varies

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

Price per night from

$385

Responds fast!
avg. 3 hours 50 minutes

Price per night from

$385

Distance approx 18.42 km from Stockbridge

16

Light Filled Mountain Retreat Near Killington and Okemo - sleeps 6

Vermont / Plymouth

Plymouth house

2 6 3 nights min

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

Price per night from

$252

Price per night from

$252

Distance approx 9.75 km from Stockbridge

24

Glazebrook-Killington Townhome - 1 Mi to Snowshed!

Vermont / Killington

Killington house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$234

Responds fast!
avg. 2 hours 55 minutes

Price per night from

$234

Distance approx 10.28 km from Stockbridge

24

Mt Green 1-C8 ~ RA80777

Vermont / Killington

Killington apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary

Price per night from

$160

Responds fast!
avg. 3 hours 50 minutes

Price per night from

$160

Distance approx 11.05 km from Stockbridge

42

Spacious home w/ large deck, hot tub, movie room & sauna!

Vermont / Killington

Killington house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Car not necessary

Price per night from

$350

Price per night from

$350

Distance approx 8.23 km from Stockbridge

38

A shared indoor pool, hot tub, gym & shuttle to the slopes!

Vermont / Killington

Killington house

2 6 min stay varies

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

Price per night from

$92

Price per night from

$92

Distance approx 12.64 km from Stockbridge

40

Gorgeous townhouse with private sauna, ski-in/ski-out access to Sunrise!

Vermont / Killington

Killington house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$368

Price per night from

$368

Distance approx 12.54 km from Stockbridge

51

Ski-in/ski-out at this Killington Resort condo w/ tennis & shared pool & hot tub

Vermont / Killington

Killington house

2 6 min stay varies

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

Price per night from

$137

Price per night from

$137

Distance approx 8.43 km from Stockbridge

(1) Excellent 

41

Townhome near ski slopes w/ shared hot tub, pool & private sauna!

Vermont / Killington

Killington house

2 6 min stay varies

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

Price per night from

$217

Price per night from

$217

Distance approx 12.57 km from Stockbridge

(3) Excellent 

56

Ski-in/ski-out Sunrise townhome w/ shared pool & hot tub for year-round retreats

Vermont / Killington

Killington house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$157

Price per night from

$157

Distance approx 12.56 km from Stockbridge

(1)  

43

Ski-in/ski out from this cozy Vermont condo w/ shared pool, hot tub, & two decks

Vermont / Killington

Killington house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$169

Price per night from

$169

Distance approx 12.6 km from Stockbridge

43

Ski-in/ski-out condo with views & access to a pool, hot tubs, a gym, and tennis!

Vermont / Killington

Killington house

3 4 min stay varies

  • 3 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$111

Price per night from

$111

Distance approx 8.08 km from Stockbridge

26

A private balcony, forest views, walk to Pico Mountain!

Vermont / Killington

Killington house

3 9 min stay varies

  • 3 bedrooms
  • sleeps 9
  • min stay varies
  • Child Friendly
  • Car not necessary

Price per night from

$122

Price per night from

$122

Distance approx 8.42 km from Stockbridge

37

Ski-in/ski-out condo w/ shared, heated pool at the base of Pico Mountain

Vermont / Killington

Killington house

1 4 min stay varies

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

Price per night from

$61

Price per night from

$61

Distance approx 8.31 km from Stockbridge

45

Ski-themed home close to slopes with a community pool, hot tub & gym!

Vermont / Killington

Killington house

2 6 min stay varies

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

Price per night from

$94

Price per night from

$94

Distance approx 12.56 km from Stockbridge

31

Ski-in/ski-out getaway w/ private deck, shared pool & hot tub

Vermont / Killington

Killington house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$299

Price per night from

$299

Distance approx 8.25 km from Stockbridge

42

Comfortable condo w/ shared pool, hot tub & more - ski access nearby!

Vermont / Killington

Killington house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$135

Price per night from

$135

Distance approx 8.28 km from Stockbridge

39

Recently updated home w/ shared hot tub, pool & more - easy ski access!

Vermont / Killington

Killington house

2 6 min stay varies

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

Price per night from

$122

Price per night from

$122

Distance approx 8.26 km from Stockbridge

40

Cozy townhome w/ sauna, a shared pool and hot tub, close to two mountain resorts

Vermont / Killington

Killington house

2 6 min stay varies

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

Price per night from

$143

Price per night from

$143