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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Pittsfield apartments

Property grounds

Vermont Suite | 10 Min to Woodstock & Killington

Vermont Suite | 10 Min to Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (5 reviews)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
The price is AED 441
AED 896 total
includes taxes & fees
19 Jan - 20 Jan
Vermont Suite | 10 Min to Woodstock & Killington
Dining

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.6 out of 10, Exceptional, (5 reviews)
"Peaceful stay in the city! We were headed to the rodeo, so this was the perfect distance away! "
United States
Aislinn F.
The price is AED 281
AED 689 total
includes taxes & fees
26 Jan - 27 Jan
Cozy Rutland Retreat
1 bedroom, desk, iron/ironing board, free WiFi

The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Place was great"
United States
Nathan H.
The price is AED 407
AED 1,125 total
includes taxes & fees
19 Jan - 20 Jan
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
Fridge, microwave, oven, stovetop

Jack S`Bearo - Slopes, Fireplace, Pool.

Jack S`Bearo - Slopes, Fireplace, Pool.
Killington
10.0 out of 10, Exceptional, (14 reviews)
"My husband and i really enjoyed our stay at Jack S'bearo! Was a nice, cozy condo for a couple or a small family. Highly recommend!"
United States
Erin
The price is AED 472
AED 1,185 total
includes taxes & fees
20 Jan - 21 Jan
Jack S`Bearo - Slopes, Fireplace, Pool.
Exterior

Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.

Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.
The Woods
7.4 out of 10, Good, (3 reviews)
"Room was great for the 140 price point it normally is, not the 250 price for World Cup weekend. Would stay again though, very convenient. Checkin was super easy and the room was clean, just needs "
United States
Joe S.
The price is AED 387
AED 1,095 total
includes taxes & fees
19 Jan - 20 Jan
Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.
Indoor pool

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.2 out of 10, Good, (45 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
The price is AED 309
AED 1,087 total
includes taxes & fees
10 Feb - 11 Feb
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Property grounds

Doc's Lake house 1st floor, 2 bedroom apartment

Doc's Lake house 1st floor, 2 bedroom apartment
Salisbury
10.0 out of 10, Exceptional, (74 reviews)
"Doc runs a great place for all to enjoy. "
United States
William D.
The price is AED 496
AED 745 total
includes taxes & fees
23 Jan - 24 Jan
Doc's Lake house 1st floor, 2 bedroom apartment
Golf

LilBear- Shuttle, FIreplace, Pool, Hot Tub.

LilBear- Shuttle, FIreplace, Pool, Hot Tub.
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Great location and comfortable condo."
United States
Timothy R.
The price is AED 496
AED 1,278 total
includes taxes & fees
26 Jan - 27 Jan
LilBear- Shuttle, FIreplace, Pool, Hot Tub.
Golf

BearNecessities- Pool, Hot Tub, Gym

BearNecessities- Pool, Hot Tub, Gym
Killington
10.0 out of 10, Exceptional, (2 reviews)
"The unit was right across from Killington with many great amenities. The place was very cozy and perfect for a quick stay before a day of skiing."
United States
Matthew S.
The price is AED 559
AED 1,333 total
includes taxes & fees
26 Jan - 27 Jan
BearNecessities- Pool, Hot Tub, Gym
Terrace/patio

Wade`s World Ski Home FirePlace Shuttle location

Wade`s World Ski Home FirePlace Shuttle location
2.0 star property
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Perfectly described and so close the mountain. All you need!"
United States
Dana E.
The price is AED 918
AED 1,990 total
includes taxes & fees
20 Jan - 21 Jan
Wade`s World Ski Home FirePlace Shuttle location
Indoor pool

Spacious mountain studio with free WiFi & full kitchen - close to skiing

Spacious mountain studio with free WiFi & full kitchen - close to skiing
Killington
6.4 out of 10, (20 reviews)
"Communication was excellent and service was great."
United States
Emmanuella A.
The price is AED 408
AED 1,288 total
includes taxes & fees
20 Jan - 21 Jan
Spacious mountain studio with free WiFi & full kitchen - close to skiing
Property grounds

Vermont Double Queen Suite | 10 min to Killington

Vermont Double Queen Suite | 10 min to Killington
Bridgewater
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is AED 470
AED 932 total
includes taxes & fees
28 Jan - 29 Jan
Vermont Double Queen Suite | 10 min to Killington
Property grounds

Vermont Suite | Killington-Woodstock-Long Trail

Vermont Suite | Killington-Woodstock-Long Trail
Bridgewater
8.0 out of 10, Very Good, (2 reviews)
"clean, easy to check in and out, convenient location to the GMHA grounds - we stay here every summer! "
United States
Amanda K.
The price is AED 404
AED 852 total
includes taxes & fees
19 Jan - 20 Jan
Vermont Suite | Killington-Woodstock-Long Trail
Interior

Trails Together! Pool, Hot Tub, Sauna, Near Resort

Trails Together! Pool, Hot Tub, Sauna, Near Resort
2.0 star property
Killington
10.0 out of 10, Exceptional, (1 review)
"Our stay was great. The condo was spacious with plenty of storage space. Everything we needed was there. The hosts were quickly responsive to questions. The welcome treats were such a nice touch."
United States
Stephanie D.
Trails Together! Pool, Hot Tub, Sauna, Near Resort
Property grounds

Vermont Suite | 10 Min to Killington & Woodstock

Vermont Suite | 10 Min to Killington & Woodstock
Bridgewater
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is AED 404
AED 852 total
includes taxes & fees
28 Jan - 29 Jan
Vermont Suite | 10 Min to Killington & Woodstock
Exterior

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Killington
9.0 out of 10, Wonderful, (7 reviews)
"Great room, plenty of amenities, close to restaurants and mountains"
United States
Daniel T.
The price is AED 869
AED 1,231 total
includes taxes & fees
20 Jan - 21 Jan
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Interior

MightyMoose- Pool, Hot tub, Sauna, Gym, Near Resort

MightyMoose- Pool, Hot tub, Sauna, Gym, Near Resort
Killington
10.0 out of 10, Exceptional, (4 reviews)
"The condo was perfect! "
United States
Mandy b.
MightyMoose- Pool, Hot tub, Sauna, Gym, Near Resort
Golf

BaseLoj - Hot tub, Pool, Sauna, Shuttle On/Off

BaseLoj - Hot tub, Pool, Sauna, Shuttle On/Off
Killington
10.0 out of 10, Exceptional, (3 reviews)
"Loved it, clean, feels like home will come again!"
United States
Theresa R.
BaseLoj - Hot tub, Pool, Sauna, Shuttle On/Off
Golf

Bearitime Lodge - Pool, Gym, Hot Tub, Location.

Bearitime Lodge - Pool, Gym, Hot Tub, Location.
Killington
8.0 out of 10, Very Good, (1 review)
"Overall, property was excellent. Only issue was no ac. A fan was provided but air was not moving in the little apartment. It was also unusually hot when were there. Location was excellent for all the hiking we had planned :-)"
United States
Kim C.
Bearitime Lodge - Pool, Gym, Hot Tub, Location.
Fridge, microwave, oven, stovetop

Rutland-Killington Mountain Midway: Refreshed 2BR Flat with High-End Kitchen and Spa Shower

Rutland-Killington Mountain Midway: Refreshed 2BR Flat with High-End Kitchen and Spa Shower
2.0 star property
Rutland
10.0 out of 10, Exceptional, (1 review)
"Super cute until - very recently updated with beautiful and clean appliances. Perfectly located "
United States
Gabrielle C.
The price is AED 568
AED 1,744 total
includes taxes & fees
19 Jan - 20 Jan
Rutland-Killington Mountain Midway: Refreshed 2BR Flat with High-End Kitchen and Spa Shower
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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Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Check in service Breakfast"
Dustin 1-night trip
Posted 23 hours ago
The Mountain Inn at Killington

Frequently asked questions

What's it like to stay at an apartment in Pittsfield?
There are plenty of places to stay in Pittsfield with 40 hotels and other lodging accommodations. Though there aren't many apartments, we can help you find similar accommodations. When you search on Expedia, you can filter by amenities you might find in an apartment such as a kitchen. Even filter by similar properties such as vacation homes, condos, or cabins. Make time to visit the region's favorite places like Killington Resort.
Why would you choose an apartment over a traditional hotel room?
An apartment is often more spacious than a traditional hotel room and includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home, and also for solo travelers who want to stay in a quieter area.
What's the best apartment for a stay in Pittsfield?
Here is a popular apartment in the area to consider: Mountain Green Resort: Located in Killington, 9.9 mi/15.9 km from the heart of Pittsfield. Includes laundry facilities, free WiFi, and separate dining areas. Free parking and an outdoor pool are on site.
What can I expect from the weather in Pittsfield?
Though weather is just one factor, it can really affect your travel plans, especially when you're planning an extended stay in Pittsfield. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches of snowfall.
What should I see and do in Pittsfield?
While exploring the area, visit family-friendly sights like Killington Adventure Center, or get outside and enjoy nature at Green Mountain National Forest. Roger Clark Memorial Central Library and Pittsfield Town Hall are other places to visit while you're in town.
What's the best way to get to and around Pittsfield?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 18.1 mi (29.2 km) from the city center. Otherwise, you can search for flights to Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.