Compare Pittsfield Guest House Rentals
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Guest Houses in Pittsfield

The Trailside Inn
115 Coffee House Road, Killington, VT
At The Trailside Inn, guests have access to free WiFi in public areas, meeting rooms, and a library. A stay here includes free parking. Front-desk staff can assist with luggage storage and concierge services. Other amenities at this golf guesthouse include express check-out, a terrace, and a picnic area.
Breakfast included
Parking included

The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views!
The price is $869 per night
$869
includes taxes & fees
$769 per night
May 1 - May 2
Guests staying at this guesthouse enjoy ski-in/ski-out access, a hot tub, and laundry facilities. This ski guesthouse also has barbecue grills.
Hot Tub
Pet friendly

Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts
Guests staying at this guesthouse have access to a garden and barbecue grills.
Air conditioning
Parking available

Serene dog-friendly guest house with mountain views, fireplace, & firepit
Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Pet friendly
Air conditioning

110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool
The price is $157 per night
$157
includes taxes & fees
$145 per night
May 18 - May 19
Guests staying at this guesthouse enjoy a gym, a library, and laundry facilities. This smoke-free guesthouse also has barbecue grills.
Air conditioning
Gym

Salt Ash Inn
4758 Route 100A, Plymouth, VT
Guests of Salt Ash Inn enjoy free WiFi in public areas, coffee in a common area, and a library. You can take advantage of free parking if you drive. Staff members are on hand to provide tour or ticket assistance and luggage storage. Additional amenities include express check-out, a terrace, and a fireplace in the lobby.
Parking included
Free WiFi
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.
Hotel Options in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 13+
Pittsfield
9.6/10 Exceptional! (80 reviews)

Private Killington Area Inn all to Yourself!
Pittsfield
10/10 Exceptional! (38 reviews)

Comfort Inn Rutland - Killington
19 Allen St, Rutland, VT
The price is $128 per night from May 4 to May 5
$128
includes taxes & fees
$116 per night
May 4 - May 5
8/10 Very Good! (1,000 reviews)
Pittsfield Guest Houses essential information
Accommodation | 6 Guest Houses |
---|---|
Lowest Price | $128 |
Highest Price | $869 |
Popular accommodation | The Trailside Inn, The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views!, Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts, Serene dog-friendly guest house with mountain views, fireplace, & firepit, 110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool, Salt Ash Inn |
Guest Houses in Pittsfield
Most Popular
More Places To Stay in Pittsfield
Top Trending
Hotels
Cheap Hotels in BurlingtonPet Friendly Hotels in KillingtonHotels in St. JohnsburyHotels with Hot Tubs in BurlingtonHistoric Hotels in ManchesterHotels with Hot Tubs in BrattleboroLuxury Hotels in BrattleboroHotels in Essex JunctionKid Friendly Hotels in BurlingtonHotels in StoweSki Resorts & Hotels in KillingtonHotels in KillingtonHotels in BurlingtonSpa Resorts & Hotels in BurlingtonSpa Resorts & Hotels in BenningtonHotels with Kitchenettes in StoweHotels in WoodstockHotels in BenningtonGay Friendly Hotels in Brattleboro
Cars
Packages