Updating...

Enter dates for more accurate prices

Pittsfield Rentals

Filter

Bedrooms

  • Any
  • 1+ Bedrooms
  • 2+ Bedrooms
  • 3+ Bedrooms
  • 4+ Bedrooms
  • 5+ Bedrooms
  • 6+ Bedrooms
  • 7+ Bedrooms
  • 8+ Bedrooms
  • 9+ Bedrooms
  • 10+ Bedrooms
  • 11+ Bedrooms
  • 12+ Bedrooms
  • 13+ Bedrooms
  • 14+ Bedrooms
  • 15+ Bedrooms

Price range

Per night

$10 - $500

Pittsfield Rentals

244 Houses

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

Pittsfield house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$92

1 / 0

Killington area ski house

Pittsfield house

5 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 1 hour 40 minutes

Price per night from

$430

1 / 16

Charming mountain farmhouse

Pittsfield house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 3 hours 40 minutes

Price per night from

$172

1 / 27

Sweet Life

Pittsfield house

3 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 1 hour 24 minutes

Price per night from

$300

1 / 26

Silver Spring Chalet

Pittsfield house

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 1 hour 24 minutes

Price per night from

$204

1 / 31

Sweet Life ( 3-Bedroom Chalet )

Pittsfield chalet

3 bedrooms / 2 bathrooms / sleeps 20

Price per night from

$397

1 / 24

Great rentals within 20 miles that match your search

Swiss Chalet 8-Bdrooms_6 F-Bathrooms X-Mass *Grps 5+

Killington chalet

8 bedrooms / 6 bathrooms / sleeps 22

Price per night from

$257

1 / 30

Pico Resort Slopeside Condo, Killington Vermont

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$143

1 / 38

Sunrise - Timberline L-1

Killington house

3 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$386

1 / 24

Suites at killington Center

Killington condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$343

1 / 23

Hakuna Matata

Bridgewater house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$198

1 / 24

The Antler House

Plymouth house

4 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$613

1 / 24

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

Killington condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 58 minutes

Price per night from

$287

1 / 15

Mt Green 3-C4

Killington apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$218

1 / 24

Killington- 6 Bedroom, 3 Bath, Sleeps 20+. Right in the heart of Ski country!

Killington house

6 bedrooms / 3 bathrooms / sleeps 20

Price per night from

$630

1 / 53

Premier Ski-in/Ski-out Location, Sunrise Mountain

Killington apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$372

1 / 24

Mt Green 1-C8 ~ RA80777

Killington apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$161

1 / 24

Mt Green 2-E6

Killington apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$159

1 / 24

Mt Green 2-F9

Killington apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$159

1 / 24

Mt Green 3-D8

Killington apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$208

1 / 24

Mt Green 3-B15

Killington apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$169

1 / 24

The Swallow's Nest

Brandon house

2 bedrooms / 1 bathroom / sleeps 4

“Truly a beautiful experience!” We could have not asked for better accommodations or service. A lovely little "nest", a beautiful farm, well stocked kitchen, plenty of towels and pillows and linens - a rare find in some places but not here! Would have

Price per night from

$172

1 / 22

Hawks View Chalet

Stockbridge house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$437

1 / 16

Mt Green 1-B9

Killington apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$160

1 / 24

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

Brandon house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$247

1 / 26

LUXURY, hot tub, private, 6 BR, 3 BA

Killington house

5 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$630

1 / 37

Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!

Killington house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$516

1 / 23

Mt Green 1-B2

Killington apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$227

1 / 24

Killington Condo w/ Fireplace Near Skiing & Spa!

Killington apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 19 minutes

Price per night from

$144

1 / 24

Mt Green 3-C8

Killington apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$169

1 / 24

The Little House Vermont

Brandon house

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$171

1 / 15

Tanglewood Vista at Killington: Amazing Mountain Vacation Destination!

Killington house

5 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$144

1 / 47

The Farmhouse

South Pomfret house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$258

1 / 18

Upper unit of Chalet, minutes to Killington, Okemo or Woodstock

Plymouth house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$401

1 / 25

ROSE'S COZY MOUNTAINVIEW - B -

Rutland house

2 bedrooms / 2 bathrooms / sleeps 7

“Comfortable and Warm House!” We are two friends from argentina and lived in The Duplex a for two weeks and we can ensure that is a confortable and likeable house. It is fully furnished with excellent conditions. Now, we are living in The Duplex B unti

Price per night from

$77

1 / 22

The Cabin at Killington: Right Unit - Amazing Ski Home Close to Mtn & Activities

Killington house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$98

1 / 18

Mt Green 2-F6

Killington apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$169

1 / 24

Mt Green 3-A13

Killington apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$218

1 / 24
Viewing 38 of 244
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more