Rent Pittsfield Condos

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Featured Condo Rentals in Pittsfield

Luxe Trailside! Bike + Ski On/Off. Closest unit to hot tub, lift, hotel & trail!

Luxe Trailside! Bike + Ski On/Off. Closest unit to hot tub, lift, hotel & trail!

Killington VT
Stay at this ski condo in Killington. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Killington Resort and Pico Mountain at Killington ...
Opens in a new windowLuxe Trailside! Bike + Ski On/Off. Closest unit to hot tub, lift, hotel & trail!
Killington Sapphire

Killington Sapphire

Killington VT
Stay at this condo in Killington. Enjoy a fitness centre and laundry facilities. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort ...
Opens in a new windowKillington Sapphire
GREAT WHITE VIEW-SKI ON/SKI OFF-3 Trails HOT TUB & SAUNA- MONTHLY RENTALS

GREAT WHITE VIEW-SKI ON/SKI OFF-3 Trails HOT TUB & SAUNA- MONTHLY RENTALS

Killington VT
Stay at this ski condo in Killington. Enjoy free Wi-Fi, 2 outdoor pickleball courts and a fitness centre. Popular attractions Killington Resort and Pico Mountain ...
Opens in a new windowGREAT WHITE VIEW-SKI ON/SKI OFF-3 Trails HOT TUB & SAUNA- MONTHLY RENTALS
Save an average of 15% on thousands of hotels when you're signed in
Two-story, walk-to-lift condo with indoor pool, hot tub, sauna, gym & game room

Two-story, walk-to-lift condo with indoor pool, hot tub, sauna, gym & game room

Killington VT
Stay at this golf condo in Killington. Enjoy a fitness centre, laundry facilities and a pool table. Popular attractions Killington Resort and Pico Mountain at ...
Opens in a new windowTwo-story, walk-to-lift condo with indoor pool, hot tub, sauna, gym & game room
3 Bed 3 Bath Luxury Ski-In/Ski-out Condo Killington Sunrise Village Slopeside

3 Bed 3 Bath Luxury Ski-In/Ski-out Condo Killington Sunrise Village Slopeside

Killington VT
Stay at this ski condo in Killington. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Killington Resort and Pico Mountain at Killington ...
Opens in a new window3 Bed 3 Bath Luxury Ski-In/Ski-out Condo Killington Sunrise Village Slopeside
Cozy condo on ski shuttle route with free WiFi & full ktichen

Cozy condo on ski shuttle route with free WiFi & full ktichen

Killington VT
Stay at this condo in Killington. Enjoy a fitness centre, a garden and laundry facilities. Popular attractions Killington Resort and Pico Mountain at Killington ...
Opens in a new windowCozy condo on ski shuttle route with free WiFi & full ktichen
Ski-In/ski-out condo with views, pool, hot tubs, gym & tennis access

Ski-In/ski-out condo with views, pool, hot tubs, gym & tennis access

Killington VT
Stay at this ski condo in Killington. Enjoy a fitness centre, laundry facilities and tennis courts. Popular attractions Killington Resort and Pico Mountain at ...
Opens in a new windowSki-In/ski-out condo with views, pool, hot tubs, gym & tennis access
Recently updated living room, 3 bedroom has everything you need in a ski vacation property G8

Recently updated living room, 3 bedroom has everything you need in a ski vacation property G8

Killington VT
Stay at this condo in Killington. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Killington Resort and Pico Mountain at Killington Ski ...
Opens in a new windowRecently updated living room, 3 bedroom has everything you need in a ski vacation property G8
Cozy Ski in-Ski Out Condominium Killington 3 Bed 2 Bath, Sleeps 6

Cozy Ski in-Ski Out Condominium Killington 3 Bed 2 Bath, Sleeps 6

Killington VT
Stay at this condo in Killington. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Killington Resort and Pico Mountain at Killington ...
Opens in a new windowCozy Ski in-Ski Out Condominium Killington 3 Bed 2 Bath, Sleeps 6
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Pittsfield Condo Rentals essential information

Accommodation
587 Condo Rentals
Lowest Price
NZ$400
Highest Price
NZ$794
Popular accommodation
Luxe Trailside! Bike + Ski On/Off. Closest unit to hot tub, lift, hotel & trail!, Killington Sapphire, GREAT WHITE VIEW-SKI ON/SKI OFF-3 Trails HOT TUB & SAUNA- MONTHLY RENTALS, Two-story, walk-to-lift condo with indoor pool, hot tub, sauna, gym & game room, 3 Bed 3 Bath Luxury Ski-In/Ski-out Condo Killington Sunrise Village Slopeside, Cozy condo on ski shuttle route with free WiFi & full ktichen, Ski-In/ski-out condo with views, pool, hot tubs, gym & tennis access, Recently updated living room, 3 bedroom has everything you need in a ski vacation property G8, Cozy Ski in-Ski Out Condominium Killington 3 Bed 2 Bath, Sleeps 6

Top trending hotels in Pittsfield

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
The price is NZ$400 per night from 12 Jan to 13 Jan
NZ$400
12 Jan - 13 Jan 2026
includes taxes & fees
Stay at this ski hotel in Killington. Enjoy free Wi-Fi, a free ski shuttle and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowKillington Mountain Lodge, Tapestry Collection by Hilton
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is NZ$464 per night from 17 Dec to 18 Dec
NZ$464
17 Dec - 18 Dec
includes taxes & fees
Stay at this ski hotel in Killington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. Popular ...
Opens in a new windowThe Mountain Inn at Killington
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is NZ$794 per night from 6 Jan to 7 Jan
NZ$794
6 Jan - 7 Jan 2026
includes taxes & fees
Stay at this luxury resort in Woodstock. Enjoy free Wi-Fi, free valet parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowWoodstock Inn & Resort
Save an average of 15% on thousands of hotels when you're signed in
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
Fully refundableReserve now, pay when you stay
Stay at this family-friendly hotel in Killington. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the pool and the helpful staff in their ...
Opens in a new windowNorth Star Lodge and Resort
Don't see what you're looking for?
See all available properties in Pittsfield
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.