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Accommodations in Pittsfield You’ll Love

Affordable, Top-Rated Places to Stay in Pittsfield – For Every Budget

Looking for accommodation in Pittsfield (Vermont)? Discover a wide range of places to stay starting at just $50.00 per night – from hotels and bed & breakfasts to vacation rentals. Whether you're visiting for business or leisure, you'll find the perfect place that fits your budget and travel needs. Book your ideal Pittsfield accommodation today!

We found 20 Accommodations in Pittsfield and the surrounding area (within 30 miles)

Trailside Inn in Killington, USA

Trailside Inn

Inn in Killington near Pittsfield, Vermont , 115 Coffee House Road
Located in Killington and with Killington Peak reachable within 7.4 miles, Trailside Inn has concierge services, non-smoking rooms, a garden, free WiF...
  • Parking
  • Family rooms

Fabulous 17 Reviews 8.8

from $162.25 Show details »

Perfect secluded 3 bedroom cozy getaway home Hawk Landing in Pittsfield, USA

Perfect secluded 3 bedroom cozy getaway...

Holiday home in Pittsfield, Vermont , 132 Hawk Ln
Perfect secluded 3 bedroom cozy getaway home Hawk Landing is located in Pittsfield, just 8.1 miles from Gifford Woods State Park and 10 miles from Pic...
  • Pets allowed

no reviews

from $394.01 Show details »

Clear River Inn and Tavern in Pittsfield, USA

Clear River Inn and Tavern

Inn in Pittsfield, Vermont , 2614 VT-100
Located in Pittsfield, 11 miles from Killington Peak, Clear River Inn and Tavern provides accommodations with a shared lounge, free private parking, a...
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Allergy-free room

Fabulous 178 Reviews 9.0

from $150.42 Show details »

Bobs Bungalow in North Sherburne, USA

Bobs Bungalow

Holiday home in North Sherburne near Pittsfield, Vermont
Bobs Bungalow is located in North Sherburne, just 3.4 miles from Gifford Woods State Park and 5.5 miles from Pico Peak.
  • Parking
  • Pets allowed

Fabulous 4 Reviews 9.0

from $96.33 Show details »

Cricket Hill in Killington, USA

Cricket Hill

Holiday home in Killington near Pittsfield, Vermont , 414 Cricket Hill Road
Providing a garden, Cricket Hill provides accommodations in Killington.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 23 Reviews 9.0

from $256.15 Show details »

Winter Brook in Killington, USA

Winter Brook

Holiday home in Killington near Pittsfield, Vermont , 2807 Route 100N
Winter Brook offers accommodations in Killington, 7.4 miles from Killington Peak and 2.3 miles from Gifford Woods State Park.
  • Parking

no reviews

from $320.77 Show details »

Killington Area Escape with Deck, Views and Hot Tub! in Stockbridge, USA

Killington Area Escape with Deck, Views...

Holiday home in Stockbridge near Pittsfield, Vermont
Killington Area Escape with Deck, Views and Hot Tub! offers accommodations in Stockbridge, 14 miles from Killington Peak and 9.3 miles from Gifford Wo...
  • Parking

Good 3 Reviews 7.0

from $310.61 Show details »

Killington Mountain Home! HotTub & 5 min to Skiing! in Killington, USA

Killington Mountain Home! HotTub & 5 min...

Holiday home in Killington near Pittsfield, Vermont , 295 Barrows Towne Road # 2
Killington Mountain Home!
  • Parking
  • Pets allowed

Very good 7 Reviews 8.0

from $331.91 Show details »

Pittsfield Paradise in Pittsfield, USA

Pittsfield Paradise

Holiday home in Pittsfield, Vermont
Pittsfield Paradise offers accommodations in Pittsfield, 14 miles from Killington Pico Adventure Center and 20 miles from McLaughlin Falls.
  • Parking

Exceptional 1 Reviews 10.0

from $387.84 Show details »

Gnome Home Mountain Ski Chalet w/Sauna Killington in Stockbridge, USA

Gnome Home Mountain Ski Chalet w/Sauna K...

Chalet in Stockbridge near Pittsfield, Vermont , 357 Timbercrest Road
17 miles from Killington Peak in Stockbridge, Gnome Home Mountain Ski Chalet w/Sauna Killington features accommodations with access to a sauna.
  • Parking
  • Sauna

no reviews

from $380.05 Show details »

Rustic 3 bedroom home Moose Lodge in Killington, USA

Rustic 3 bedroom home Moose Lodge

Holiday home in Killington near Pittsfield, Vermont , 589 Barrows Towne Road
Rustic 3 bedroom home Moose Lodge offers accommodations in Killington, 7 miles from Killington Pico Adventure Center and 13 miles from McLaughlin Fall...

no reviews

from $429.82 Show details »

Vermont Retreat - 8 Mi to Killington Ski Area in Killington, USA

Vermont Retreat - 8 Mi to Killington Ski...

Holiday home in Killington near Pittsfield, Vermont
Vermont Retreat - 8 Mi to Killington Ski Area offers accommodations in Killington, 7.5 miles from Killington Peak and 2.5 miles from Gifford Woods Sta...
  • Parking

Very good 1 Reviews 8.0

from $62.00 Show details »

Cozy Killington Retreat about 5 Mi to Ski Resort in Killington, USA

Cozy Killington Retreat about 5 Mi to Sk...

Apartment in Killington near Pittsfield, Vermont
Cozy Killington Retreat about 5 Mi to Ski Resort offers accommodations in Killington, 7.5 miles from Killington Peak and 2.5 miles from Gifford Woods ...
  • Parking

Poor 1 Reviews 3.0

from $251.61 Show details »

Wonderful One bedroom condo located in Highridge Condominiums J6 in Killington, USA

Wonderful One bedroom condo located in H...

Holiday home in Killington near Pittsfield, Vermont , 184 Ridge Rd
8.7 miles from Killington Peak in Killington, Wonderful One bedroom condo located in Highridge Condominiums J6 offers accommodations with access to a ...
  • Sauna
  • Indoor pool
  • Swimming Pool

Exceptional 1 Reviews 10.0

from $251.45 Show details »

Hot Tub Sauna Firepit Nespresso Huge TV in Killington, USA

Hot Tub Sauna Firepit Nespresso Huge TV

Holiday home in Killington near Pittsfield, Vermont , Alran Road 214
Hot Tub Sauna Firepit Nespresso Huge TV is located in Killington, just 5.7 miles from Killington Peak and a 13-minute walk from Gifford Woods State Pa...
  • Parking

Very good 1 Reviews 8.0

from $334.63 Show details »

The Maple Leaf home in Killington, USA

The Maple Leaf home

Holiday home in Killington near Pittsfield, Vermont
The Maple Leaf home offers accommodations in Killington, 7.2 miles from Killington Peak and 2.2 miles from Gifford Woods State Park.
  • Parking

no reviews

from $1.089.10 Show details »

SnowArts-wood burning fireplace, close to slopes in Killington, USA

SnowArts-wood burning fireplace, close t...

Holiday home in Killington near Pittsfield, Vermont , 295 Barrows Towne Road Unit 1
SnowArts-wood burning fireplace, close to slopes offers accommodations in Killington, 6.8 miles from Killington Peak and 1.7 miles from Gifford Woods ...
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 1 Reviews 10.0

from $252.37 Show details »

Spacious Cabin Retreat with Hot Tub in Pittsfield, USA

Spacious Cabin Retreat with Hot Tub

Holiday home in Pittsfield, Vermont , Vermont Route 100
A recently renovated vacation home, Spacious Cabin Retreat with Hot Tub offers accommodations in Pittsfield.
  • Parking
  • Pets allowed
  • Sauna
  • Family rooms

no reviews

from $50.00 Show details »

The Getaway home in Pittsfield, USA

The Getaway home

Holiday home in Pittsfield, Vermont
The Getaway home offers accommodations in Pittsfield, 11 miles from Killington Peak and 6.4 miles from Gifford Woods State Park.
  • Parking

no reviews

from $447.13 Show details »

Swiss Farm Inn in Pittsfield, USA

Swiss Farm Inn

Hotel in Pittsfield, Vermont , 4441 Vermont Route 100
Located within 13 miles of Killington Peak and 7.9 miles of Gifford Woods State Park, Swiss Farm Inn provides rooms with air conditioning and a privat...
  • Parking

no reviews

from $1.870.71 Show details »

Number of Accommodations in Pittsfield 20
Number of guest ratings 179
Average price per night $262.00
Lowest price per night $50,00
Highest price per night $2.198,63

Top 10 Most Popular Accommodations in Pittsfield

Explore the Most Popular Accommodations in Pittsfield – Ranked by Average Guest Ratings.

Top 10 Cheapest Accommodations in Pittsfield

Discover the Cheapest Accommodations in Pittsfield – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Accommodations in Pittsfield

Check out the Most Booked Accommodations in Pittsfield – Based on Guest Popularity.

Discover Pittsfield – Your Guide to the Best Places to Stay

Planning a trip to Pittsfield? Choosing the right place to stay is one of the most important parts of making your visit memorable. Whether you are looking for a luxury hotel, a cozy guesthouse, a modern apartment, or a family-friendly vacation rental, Pittsfield offers a wide range of lodging options to suit every travel style and budget.

When deciding where to stay in Pittsfield, consider key factors like location, amenities, reviews, and proximity to attractions or public transport. Do you prefer being in the heart of the city close to restaurants, shops, and nightlife? Or do you want a quiet neighborhood with a more local feel? With so many types of accommodations in Pittsfield, from boutique hotels to spacious homes, you are sure to find something that fits your needs.

Tips for Finding the Perfect Stay in Pittsfield

To find the perfect place to stay in Pittsfield, consider your budget, preferred location, and the amenities you need. Do you want to stay in a hotel or a vacation rental or do your prefer an apartment or house with more space, privacy, and the opportunity to live like a local? Do you need access to a kitchen, laundry facilities, or a gym? Research online reviews and ratings to get an idea of what past guests have experienced. Also, consider the type of trip you're taking. If you're traveling with family, you may need a larger space or a kid-friendly environment. If you're on a romantic getaway, you may want a more intimate setting.

Accommodation data and pictures provided by Booking.com