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Tonight
Check prices in Pittsfield for tonight, Aug 26 - Aug 27
Aug 26 - Aug 27
Tomorrow night
Check prices in Pittsfield for tomorrow night, Aug 27 - Aug 28
Aug 27 - Aug 28
This weekend
Check prices in Pittsfield for this weekend, Aug 28 - Aug 30
Aug 28 - Aug 30
Next weekend
Check prices in Pittsfield for next weekend, Sep 4 - Sep 6
Sep 4 - Sep 6

Most frequently booked Pittsfield hotels

Killington area home - 4-seasons, hot tub and A/C

Killington area home - 4-seasons, hot tub and A/C

Pittsfield VT
1.53 km from city center
Get rates
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Roger Clark Memorial Central Library and Liberty Hill Farm are located nearby.
Hot tub
Kitchen
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
28.87 km from city center
The price is CA $566 per night
CA $566
CA $684 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Pool
Hot tub
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Free cancellation
Reserve now, pay when you stay
15.82 km from city center
The price is CA $173 per night
CA $173
CA $200 total
Aug 27 - Aug 28
includes taxes & fees
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Pool
Breakfast included
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Free cancellation
Reserve now, pay when you stay
15.28 km from city center
The price is CA $215 per night
CA $215
CA $237 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this golf hotel in Killington. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Hot tub
Pet-friendly
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Free cancellation
23.23 km from city center
The price is CA $185 per night
CA $185
CA $203 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vermont State Fairgrounds and Green Mountain Shopping Plaza are located nearby.
Pool
Hot tub
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
1246 Franklin Street Brandon VT
20.7 km from city center
The price is CA $224 per night
CA $224
CA $253 total
Aug 27 - Aug 28
includes taxes & fees
Book a stay at this family-friendly hotel in Brandon. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Otter Valley Winery and Stephen A Douglas Birthplace are located nearby.
Pool
Hot tub
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
2440 Vermont 66 Randolph Center VT
Free cancellation
Reserve now, pay when you stay
24.72 km from city center
The price is CA $211 per night
CA $211
CA $229 total
Aug 27 - Aug 28
includes taxes & fees
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture and Montague Golf Club are located nearby.
Pet-friendly
Parking included
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
27.85 km from city center
The price is CA $317 per night
CA $317
CA $379 total
Sep 8 - Sep 9
includes taxes & fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Union Arena Community Center and Five Elm Arches are located nearby.
Pool
Hot tub
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street Middlebury VT
Free cancellation
Reserve now, pay when you stay
37.43 km from city center
The price is CA $220 per night
CA $220
CA $242 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Middlebury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Town Hall Theater and Vermont Folklife Center are located nearby.
Parking included
Free WiFi
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.

Top hotels in Pittsfield for Extended Stay

Your Perfect Getaway Renovated and Beautifully Decorated Hotel Room Studio

Your Perfect Getaway Renovated and Beautifully Decorated Hotel Room Studio

99 Killington Center Dr Killington VT
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 hotels essential information

Accommodation
1,812 hotels
Lowest Price
CA $200
Highest Price
CA $684
Popular hotels
Killington area home - 4-seasons, hot tub and A/C, Woodstock Inn & Resort, The Mountain Inn at Killington, Killington Mountain Lodge, Tapestry Collection by Hilton, Comfort Inn Rutland - Killington, Emrose Luxury Cabins, My Place Hotel-Randolph VT, On The River Inn, Courtyard Middlebury

Frequently asked questions

What are the top kid-friendly hotels in Pittsfield?
Take some of the hassles out of traveling with young ones by choosing a family-friendly hotel in Pittsfield. From useful amenities to services that bring a smile, these stays feature perks that'll make your getaway plain sailing: The whole gang will love staying at Wintergreen 106 in Pittsfield. Housekeeping services and a fireplace are just a couple of the things that help make this hotel a sought-after option. Also look into Perfect secluded cozy getaway home Hawk Landing. It offers a water park, a nearby theme park and ample opportunities for family time.
Where can I find cheap hotels in Pittsfield?
At Travelocity you'll find really nice hotels in Pittsfield at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Pittsfield rather than in Pittsfield. We may find you even better rates, too.
How do I find the best Pittsfield hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Pittsfield then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Pittsfield?
The cheapest hotel in Pittsfield is CA $200 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Pittsfield?
There are 1,812 hotels in Pittsfield on Travelocity.
What are the best hotels in Pittsfield?
Pittsfield has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Pittsfield for you!
When is the best time to visit Pittsfield?
If you want the joy of a fun-filled trip in peak season, visit Pittsfield during November, December and January. If you'd prefer the peace of off-season, book a stay during quieter months, such as April, May and June.
When is the cheapest time to stay in Pittsfield?
Based on historic data is usually the cheapest month to visit Pittsfield. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Pittsfield?
There are multiple hotels in Pittsfield that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Pittsfield. We have plenty of kid-friendly hotels in Pittsfield to choose from on Travelocity!
Why book a hotel in Pittsfield through Travelocity?
Because we have the top hotels in Pittsfield! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Pittsfield on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Pittsfield hotel reviews by fellow wanderers

Emrose Luxury Cabins

Emrose Luxury Cabins

5 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Very clean and modern , Loved the hot tub just a side note it takes 2/3hrs to heat"
A verified traveller stayed at Emrose Luxury Cabins
Emrose Luxury Cabins