A lake surrounded by autumn-colored trees and a rocky shoreline.

Pittsfield Condominium Resorts to Rent

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

A spacious living room with a stone fireplace, wooden furniture, and a large potted plant.

1. The Trailside Inn

The Trailside Inn
3.0 star property
North Sherburne
9.2 out of 10, Wonderful, (167 reviews)
"Such a welcoming and friendly place for a stay"
United States
Marc
$159 nightly
The price is $175
Nov 29 - Nov 30
Total with taxes and fees
The Trailside Inn
A wooden dock with two Adirondack chairs and a blanket, overlooking a calm lake with dense forest in the background.

2. Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (370 reviews)
"This place is awesome, Clean, beautiful, great location, great staff, super breakfast."
United States
Kathy
$165 nightly
The price is $181
Nov 30 - Dec 1
Total with taxes and fees
Mountain Meadows Lodge
A dining area with a wooden table and chairs, a fireplace, and a cozy seating area with a couch and a TV.

3. Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,004 reviews)
"Would definitely stay again"
United States
Pamela
$109 nightly
The price is $120
Nov 22 - Nov 23
Total with taxes and fees
Mountain Sports Inn
A spacious living room with a high ceiling, wooden beams, a staircase, and a large window.

4. Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (706 reviews)
"Very friendly staff with easy check in and out. Breakfast was fast and convenient and great location!"
United States
Jeff
$174 nightly
The price is $190
Dec 7 - Dec 8
Total with taxes and fees
Greenbrier Inn
A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a view of the outdoors.

5. North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1,000 reviews)
"Perfect service and friendly staff!!"
United States
Toghrul
$131 nightly
The price is $144
Nov 8 - Nov 9
Total with taxes and fees
North Star Lodge and Resort
A wooden structure with a black door labeled "KILLINGTON HAUS GUEST ENTRANCE" and a sign saying "WELCOME GUESTS!".

6. Killington Haus

Killington Haus
2.0 star property
Killington
9.2 out of 10, Wonderful, (71 reviews)
"Clean room, clean place, warm and cozy inside. A great place to stay in Killington!"
United States
Ivan
$121 nightly
The price is $133
Nov 7 - Nov 8
Total with taxes and fees
Killington Haus
A spacious room with large windows, a stone wall, and a wooden ceiling.

7. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (132 reviews)
"Oh wow!! I would stay here again tomorrow! Beautiful property, restaurant has amazing food and convenient location. We stayed in the Long View Barn, the 60 mile view was even more spectacular than we imagined!"
United States
Allison
$340 nightly
The price is $371
Nov 8 - Nov 9
Total with taxes and fees
The Mountain Top Inn & Resort
A building with a modern design, featuring large windows and a covered outdoor seating area.

8. The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,004 reviews)
"Great hotel!"
United States
Petra
$156 nightly
The price is $172
Nov 8 - Nov 9
Total with taxes and fees
The Mountain Inn at Killington
A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

9. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (435 reviews)
"It was a fantastic stay and all that we wanted in a charming inn on the mountain."
United States
Marleen
$152 nightly
The price is $167
Dec 6 - Dec 7
Total with taxes and fees
Snowed Inn
A sign for 'Apres Inn' in KILLINGTON, VT, with a modern building featuring large windows and a balcony.

10. Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (208 reviews)
"modern and clean, wifi worked great"
United States
Kylie
$138 nightly
The price is $152
Nov 11 - Nov 12
Total with taxes and fees
Après Inn Killington
A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

11. Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (7 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
$457 nightly
The price is $481
Nov 8 - Nov 9
Total with taxes and fees
Gnome Home Mountain Ski Chalet w/Sauna Killington
A wooden shed with a cross-braced door in a garden with a house in the background.

12. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings
North Sherburne
8.0 out of 10, Very good, (17 reviews)
"We had a great time!"
United States
Matthew R.
$324 nightly
The price is $367
Nov 8 - Nov 9
Total with taxes and fees
Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings
A large, multi-story hotel with a prominent entrance and a staircase leading to the upper levels.

13. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
Killington
7.4 out of 10, Good, (1,001 reviews)
"Great hotel with an amazing staff."
United States
Richard
$143 nightly
The price is $158
Nov 12 - Nov 13
Total with taxes and fees
Killington Mountain Lodge, Tapestry Collection by Hilton
A spacious indoor area with a large dining table, several chairs, and a sofa. There is a glass door leading outside, and the room has a wooden ceiling structure.

14. Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,000 reviews)
"clean, staff welcoming, and breakfast was solid."
United States
Bryce
$161 nightly
The price is $177
Nov 12 - Nov 13
Total with taxes and fees
Best Western Inn & Suites Rutland-Killington
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

15. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Killington
9.4 out of 10, Exceptional, (10 reviews)
"Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . "
United States
Asad B.
$234 nightly
The price is $264
Nov 8 - Nov 9
Total with taxes and fees
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

16. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
9.8 out of 10, Exceptional, (14 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
$282 nightly
The price is $319
Nov 8 - Nov 9
Total with taxes and fees
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A hotel lobby with a reception desk, seating area, and a coffee table with a fruit basket.

17. Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1,001 reviews)
"This was a good hotel for a decent price."
United States
Leila
$125 nightly
The price is $138
Nov 12 - Nov 13
Total with taxes and fees
Comfort Inn Rutland - Killington
Front of property

18. Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (733 reviews)
"Very unique and well maintained/restored historic property. It's a cool place."
United States
Amy
$118 nightly
The price is $130
Dec 7 - Dec 8
Total with taxes and fees
Brandon Inn
A spacious living room with a fireplace, a television, and a large window.

19. 4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly
North Sherburne
10.0 out of 10, Exceptional, (24 reviews)
"Our group had a wonderful ski weekend at the house! It was well stocked with everything we needed and the fireplace was perfect to relax near after a day on the slopes. "
United States
Christina V.
$598 nightly
The price is $676
Nov 8 - Nov 9
Total with taxes and fees
4BR Killington Home Perfect for Families, Pet-Friendly
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"We loved our spacious room, the sauna, pool/hot tub and game room! We were welcomed with a s’mores pack and spent the evening by the cozy fire pit. Lovely hotel!"
Rachel 1-night trip
Posted less than an hour ago
On The River Inn

Find out more about Pittsfield

Pittsfield Condo Resorts information

Number of reviews
1,131
Accommodation
0 Condo Resorts
Lowest Price
$120
Highest Price
$676

Explore a world of travel with Expedia