Gog_sr_cc_less
Skip to main content

Filter by:

Review score
Property type
Travel group
Smart filters
Brands
Fun things to do
Certifications
Entire places
Facilities
Room facilities
Distance from centre of Pittsfield
Landmarks
Property rating
Find high-quality hotels and holiday rentals
Property accessibility
Room accessibility

Pittsfield: 16 properties found

Save up to 40% on stays

Book now with free cancellation and no hidden fees, stay till 31 Dec 2026.
A double bed in front of large Black Friday logo
1.2 miles from centre
Bar
Located in Pittsfield, 18 km from Killington Mountain, Clear River Inn and Tavern provides accommodation with a shared lounge, free private parking, a restaurant and a bar.
0.6 miles from centre
Located in Pittsfield in the Vermont region, Perfect secluded 3 bedroom cozy getaway home Hawk Landing has a balcony. This holiday home features accommodation with a patio.
1.3 miles from centre
Silver Spring Chalet is situated in Pittsfield, 14 km from Gifford Woods State Park, 18 km from Pico Peak, and 44 km from Mount Tom.
0.5 miles from centre
Situated 18 km from Pico Peak, 43 km from Mount Tom and 20 km from Killington Pico Adventure Center, Swiss Farm Inn - Entire Inn to Yourself provides accommodation set in Pittsfield.
0.9 miles from centre
Located in Pittsfield, this villa is 10 km from Killington. The property is 28 km from Woodstock and boasts views of the mountains.
0.9 miles from centre
Hot tub/Jacuzzi
Sweet Life Brought to you by GetAway Vacations is located in Pittsfield, 20 km from Killington Mountain, 11 km from Gifford Woods State Park, as well as 17 km from Pico Peak.
0.6 miles from centre
Terrace
Situated 22 km from Killington Mountain and 13 km from Gifford Woods State Park in Pittsfield, Mountain Top Fresh Pond Hot Tub offers accommodation with a kitchen.
0.9 miles from centre
Situated 20 km from Killington Mountain and 11 km from Gifford Woods State Park in Pittsfield, Sweet Life offers accommodation with a kitchen.
0.7 miles from centre
Set in Pittsfield, 20 km from Pico Peak and 46 km from Mount Tom, Serene Architect-Designed Vermont Chalet home offers air conditioning.
1.3 miles from centre
Situated in Pittsfield, Silver Spring Chalet Brought to you by GetAway Vacations features accommodation with heated pool, free WiFi and free private parking for guests who drive.
1.6 miles from centre
Hot tub/Jacuzzi
Located 16 km from Pico Peak, The Getaway home offers accommodation in Pittsfield with access to a hot tub.
3.7 miles from centre
Located in Pittsfield in the Vermont region, Experience the charm of Peak Hill Home, a cozy 3-BR retreat close to Ski Resort features a patio.
8.2 miles from centre
Restaurant
Situated in Pittsfield, 44 km from Killington Mountain and 22 km from Mount Tom, The Cabin at Fort Defiance features a restaurant. Guests can benefit from a balcony and a children's playground.
1.3 miles from centre
Located in Pittsfield in the Vermont region, Silver Spring Chalet Spacious 4BR Retreat 1888 has a patio.
1.7 miles from centre
Restaurant
Set in Pittsfield, 23 km from Killington Mountain and 14 km from Gifford Woods State Park, Pittsfield Paradise offers a restaurant. Guests staying at this holiday home have access to a balcony.
8.2 miles from centre
Restaurant
Boasting air-conditioned accommodation with a balcony, The Cabin & Loft Fort Defiance is situated in Pittsfield. Guests can benefit from a patio and a children's playground.
1.8 miles from Pittsfield
Hot tub/Jacuzzi
Featuring air-conditioned accommodation with a balcony, Killington Area Escape with Deck, Views and Hot Tub! is located in Stockbridge. This holiday home provides accommodation with a patio.
2.6 miles from Pittsfield
Boasting air-conditioned accommodation with a patio, Gnome Home Mountain Ski Chalet w/Sauna Killington is situated in Stockbridge.
4.4 miles from Pittsfield
Terrace
Featuring a garden, private pool and garden views, Cricket Hill Lodging is located in Killington. Boasting private check-in and check-out, this property also provides guests with a picnic area.
5.3 miles from Pittsfield
Situated 11 km from Killington Mountain, Killington Mountain Home! HotTub & 5 min to Skiing! features accommodation with free WiFi and free private parking.
5 miles from Pittsfield
Situated 34 km from Killington Mountain, The Maple House features accommodation with free WiFi and free private parking. The air-conditioned accommodation is 26 km from Gifford Woods State Park.
4.9 miles from Pittsfield
Situated in Killington, 12 km from Killington Mountain, Trailside Inn features accommodation with a garden, free private parking, a shared lounge and a tennis court.
6.2 miles from Pittsfield
Hot tub/Jacuzzi
Boasting accommodation with a patio, Renovated 4BR House - Hot Tub, Game Room & Fire Pit - 11 Mins to Killington Lifts & Dining is located in Telemark Village.
New to Booking.com
4.4 miles from Pittsfield
Hot tub/Jacuzzi
Killington A-Frame home, a property with a garden, is set in Killington, 12 km from Pico Peak, 39 km from Mount Tom, as well as 13 km from Killington Pico Adventure Center.
4.1 miles from Pittsfield
Located in Killington in the Vermont region, Mountainview Escape home provides accommodation with free WiFi and free private parking.
gogless