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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Apartments in Pittsfield

Nana's House
Exterior detail

Nana's House

10.0 out of 10, Exceptional, (44)
"I'm not much for reviews, but everything about this place was perfect! We can't wait to go back!"
Nana's House
Vermont Retreat
Fridge, microwave, oven, stovetop

Vermont Retreat

10.0 out of 10, Exceptional, (28)
"Lovely banana bread greeted me when I arrived and there was fresh milk and orange juice as well. A bit off the beaten track, but a lovely one bedroom apartment just right for a weekend in Vermont. "
Vermont Retreat
SlopeSide Chalet - Pool, Grill, Hot tub, Views!
Outdoor dining

SlopeSide Chalet - Pool, Grill, Hot tub, Views!

10.0 out of 10, Exceptional, (17)
"Beautiful and great location."
The price is AED 2,166
AED 4,312 total
includes taxes & fees
5 Oct - 6 Oct
SlopeSide Chalet - Pool, Grill, Hot tub, Views!
Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi
Microwave, oven, stovetop, coffee/tea maker

Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi

8.0 out of 10, Very Good, (1)
"The loft space is cute. Just know there is another house that is also rented out and it’s right next to this garage loft. I didn’t expect it to be so close. "
Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
Outdoor dining

Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily

9.0 out of 10, Wonderful, (18)
"Nice house in a great area"
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
Long Trail Suite | 10 Mins to Mountains | A/C
Exterior

Long Trail Suite | 10 Mins to Mountains | A/C

8.0 out of 10, Very Good, (2)
"clean, easy to check in and out, convenient location to the GMHA grounds - we stay here every summer! "
The price is AED 463
AED 920 total
includes taxes & fees
28 Oct - 29 Oct
Long Trail Suite | 10 Mins to Mountains | A/C
SugarBear- Pool, AC, Sauna, Gym, Tennis!
Indoor pool, a heated pool

SugarBear- Pool, AC, Sauna, Gym, Tennis!

10.0 out of 10, Exceptional, (6)
"Great stay. Place was as advertised. Owners were very accommodating and helpful. Would stay there again. "
SugarBear- Pool, AC, Sauna, Gym, Tennis!
Holiday Haus- AC, game room, near golf
Fridge, microwave, oven, stovetop

Holiday Haus- AC, game room, near golf

10.0 out of 10, Exceptional, (2)
"We had a wonderful time, the house is very well appointed and was spotless!! Great location, plan to return next year."
The price is AED 995
AED 2,592 total
includes taxes & fees
1 Oct - 2 Oct
Holiday Haus- AC, game room, near golf
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Indoor pool, a heated pool

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

10.0 out of 10, Exceptional, (6)
"Great location and a great place. Felt right at home"
The price is AED 555
AED 1,927 total
includes taxes & fees
6 Oct - 7 Oct
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Modern Ski Château - 4 min from Killington Ski mountain lifts
Fridge, oven, stovetop, dishwasher

Modern Ski Château - 4 min from Killington Ski mountain lifts

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay- it was perfect for our family of 4. Easy access to Killington and Pico and the pool was a great bonus for the kids!"
The price is AED 4,966
AED 7,135 total
includes taxes & fees
1 Oct - 2 Oct
Modern Ski Château - 4 min from Killington Ski mountain lifts
Beartopia- Hot Tub, Views, 2 Primary Suites!
Exterior

Beartopia- Hot Tub, Views, 2 Primary Suites!

Beartopia- Hot Tub, Views, 2 Primary Suites!
Red Clover Inn: Queen Suite near Killington
Exterior

Red Clover Inn: Queen Suite near Killington

8.8 out of 10, Excellent, (3)
"We stayed there again for the second weekend in a row and again it was charming and comfortable. The community rooms are especially spacious and show off the beautiful grounds outside the large windows. Carol was over the top attentive to our needs. It was a lovely relaxing stay."
Red Clover Inn: Queen Suite near Killington
The Killington Chalet, Hot Tubs, Sauna, Boot Dryer
TV, fireplace

The Killington Chalet, Hot Tubs, Sauna, Boot Dryer

The Killington Chalet, Hot Tubs, Sauna, Boot Dryer
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Property grounds

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

7.2 out of 10, Good, (44)
"Quick trip to and from Killington mt"
The price is AED 257
AED 958 total
includes taxes & fees
1 Oct - 2 Oct
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Centrally located apartment for the skier & outdoor enthusiast
Fridge, microwave, oven, stovetop

Centrally located apartment for the skier & outdoor enthusiast

2.0 star property
4.0 out of 10, (1)
"The oven didn’t work and couldn’t get anyone to come turn a breaker back on! "
The price is AED 511
AED 1,225 total
includes taxes & fees
5 Oct - 6 Oct
Centrally located apartment for the skier & outdoor enthusiast
Doc's Lake house 1st floor, 2 bedroom apartment
Exterior

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

10.0 out of 10, Exceptional, (69)
"Very clean, cozy spot right across from the lake."
Doc's Lake house 1st floor, 2 bedroom apartment
Ben & Jerry Suite | Minutes to Woodstock | Hiking
Interior

Ben & Jerry Suite | Minutes to Woodstock | Hiking

9.6 out of 10, Exceptional, (5)
"Pleasant and convenient. "
The price is AED 400
AED 840 total
includes taxes & fees
28 Oct - 29 Oct
Ben & Jerry Suite | Minutes to Woodstock | Hiking
DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room
Property grounds

DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room

10.0 out of 10, Exceptional, (20)
"Thanks to Holly and Dan for another fabulous stay at their amazing Killington house. Perfect for large family / friend groups."
The price is AED 1,269
AED 3,709 total
includes taxes & fees
1 Oct - 2 Oct
DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room
2 Queens | 10 Mins to the Mountains | Foliage
Iron/ironing board, WiFi, bed sheets

2 Queens | 10 Mins to the Mountains | Foliage

8.6 out of 10, Excellent, (4)
"As advertised"
The price is AED 525
AED 996 total
includes taxes & fees
28 Oct - 29 Oct
2 Queens | 10 Mins to the Mountains | Foliage
Yurt in Middlebury, Vermont
Exterior

Yurt in Middlebury, Vermont

10.0 out of 10, Exceptional, (3)
"It was an awsome experience. Best glamping ever"
Yurt in Middlebury, Vermont
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
"Very easy check-in. Lovely staff, very friendly, and helpful. The only thing missing is a tea coffee maker in the room. Otherwise, everything else is excellent."
Patricia 1-night trip
Posted 5 days ago
The Mountain Inn at Killington

Frequently asked questions

What's it like to stay at an apartment in Pittsfield?
You'll find plenty of places to stay in Pittsfield with 40 accommodations. Though there aren't many apartments, we can help you locate 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 guest houses.
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 are some of the more popular apartments in the area: Vermont Retreat: Situated in Bridgewater, 15.9 mi/25.6 km from the heart of Pittsfield. Includes free WiFi and Smart TVs. Nana's House: Located 15.9 mi/25.6 km away in Bridgewater. Free WiFi and Smart TVs are included. Clean & bright condo with mountain views & modern kitchen - walk to lifts: Located in Killington, 9.9 mi/15.9 km away. Includes sofa beds. A fitness center and onsite laundry facilities are on site. SlopeSide Chalet - Pool, Grill, Hot tub, Views!: Located 12.3 mi/19.7 km away in Killington. Free WiFi, private balconies, and fireplaces are included. A fitness center and onsite laundry facilities 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.