Skip to main content

Cottages in Pittsfield

Find the cottages that appeal to you the most

August 2026

1
2345678
9101112131415
16171819202122
23242526272829
3031

September 2026

12345
6789101112
13141516171819
20212223242526
27282930
Flexible date options
Select occupancy

The best cottages in Pittsfield

Check out our selection of great cottages in Pittsfield

Show hotels on map

Filter by:

Review score

NEW Skye Ridge Carriage House with Hot Tub

Killington (Near Pittsfield)

5.1 miles from Gifford Woods State Park in Killington, NEW Skye Ridge Carriage House with Hot Tub features accommodations with access to a hot tub.

H
Holobetz
From
United States
The accommodations were perfect for a small group yet roomy enough that you did not feel crowded. Beds were very comfortable - not too soft or firm. Proximity to skiing, shopping, and dining was perfect. Was quiet and serene. Loved almost everything - could have used a second shower.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
$327.85
1 night, 2 adults
Check availability

Cozy Rutland Retreat

Rutland (Near Pittsfield)

Cozy Rutland Retreat is located in Rutland, just 22 miles from Pico Peak and 6.4 miles from Mclaughlin Falls.

S
Stacy
From
United States
It was ina good location. The owner was super helpful and kind
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 12 reviews
Price from
$154
1 night, 2 adults
Check availability

Highridge B14 Enjoy the view ski back trail shuttle service sports center

Killington (Near Pittsfield)

2.1 miles from Killington Peak in Killington, Highridge B14 Enjoy the view ski back trail shuttle service sports center offers accommodations with free Wifi and access to a sauna, hot tub, and fitness...

A
Amanda
From
United States
Location, view, cleanliness, sauna
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 8 reviews
Check availability

Walk to Lifts & Village! Killington Mountain Condo

Killington (Near Pittsfield)

A 18-minute walk from Killington Peak in Killington, Walk to Lifts & Village! Killington Mountain Condo features accommodations with access to a hot tub.

N
Nicholas
From
United States
Great location. Tanya is the best!
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 15 reviews
Check availability

Killington/ Rutland 2 bedroom Cabin, cabin #4

Killington (Near Pittsfield)

7.9 miles from Killington Peak in Killington, Killington/ Rutland 2 bedroom Cabin, cabin #4 provides accommodations with access to a spa center.

J
Justin
From
United States
Robert was great, he texted me prior to my arrival and met me at the cabin where he briefly went over everything with the cabin (super nice!). The cabin was comfortable with 2 clean bathrooms and a shared shower that was easily accessible from both rooms. The living area had a couch with 2 twin beds that folded out, great for kids. Fireplace was great! Also a side room off one of the of the bedrooms that was accessible from outside to store ski gear. I would highly recommend these cabins and would stay here again.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 26 reviews
Check availability

Ski in/out Spruce Glen Townhomes on Great Eastern Trail

Killington (Near Pittsfield)

Providing free Wifi, private parking, and ski-to-door access, the recently renovated property Ski in/out Spruce Glen Townhomes on Great Eastern Trail offers rooms in Killington, 2.5 miles from...

L
Laurie
From
United States
This condo has a great ski out location.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 27 reviews
Check availability

Cozy 2-Bedroom Northbrook #3 with Fireplace

Killington (Near Pittsfield)

Cozy 2-Bedroom Northbrook #3 with Fireplace offers accommodations in Killington, 3.5 miles from Killington Peak and 3.7 miles from Gifford Woods State Park.

K
Kristin
From
United States
Great space and location! Staff was amazing whenever we chatted with them! Close to the mountain and resteraunts.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 5 reviews
Check availability

Tranquil Peaks Studio at KCIS - Perfect for a Getaway in the Heart of Vermont Ski Resort

Killington (Near Pittsfield)

Tranquil Peaks Studio at KCIS - Perfect for a Getaway in the Heart of Vermont Ski Resort offers accommodations in Killington, 1.8 miles from Gifford Woods State Park and 4.2 miles from Pico Peak.

E
Emily
From
United States
Great and inexpensive place located close to Killington ski resort
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 6 reviews
Check availability

Charming Killington Center Studio Condo #341 on the Bus Route - Summer Pool

Killington (Near Pittsfield)

Charming Killington Center Studio Condo #341 on the Bus Route - Summer Pool is located in Killington, just 3.1 miles from Killington Pico Adventure Center and 11 miles from Mclaughlin Falls.

C
C joseph
From
Italy
The location was excellent.The facilities was in top condition got to enjoy the pool
Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 9 reviews
Check availability

Killington Center 131

Killington (Near Pittsfield)

Killington Center 131 is located in Killington, just 1.8 miles from Gifford Woods State Park and 4.2 miles from Pico Peak. Guests can go for a swim in the heated pool.

T
Theresia
From
United States
Accessibility to dining and shops
Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 10 reviews
Check availability
All cottages in Pittsfield

Looking for a cottage?

Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.

Most booked cottages in Pittsfield and surrounding area in the past month

See all

Popular with guests booking cottages in Pittsfield

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking cottages in Barnard

Popular with guests booking cottages in Rochester

Scored out of 10, guest rating 7.5
Good - What previous guests thought, 2 reviews

Popular with guests booking cottages in Rochester

Traveling by car? These cottages in Pittsfield and nearby offer free parking

See all
Scored out of 10, guest rating 4.5
Disappointing - What previous guests thought, 2 reviews

Spacious Vermont Mountain Retreat - 4BR,4BA - Near Skiing & Hiking - Perfect for Groups offers accommodations in Stockbridge, 13 miles from Killington Peak and 7.7 miles from Gifford Woods State Park.

Scored out of 10, guest rating 7.5
Good - What previous guests thought, 2 reviews

14 miles from Killington Peak in Rochester, Mountain Edge A-frame features accommodations with access to a hot tub. This property offers access to a balcony, free private parking, and free Wifi.

Scored out of 10, guest rating 7.0
Good - What previous guests thought, 3 reviews

14 miles from Killington Peak in Stockbridge, Killington Cabin, Hot Tub & Foliage Views! provides accommodations with access to a hot tub.

17 miles from Killington Peak in Stockbridge, Gnome Home Mountain Ski Chalet w/Sauna Killington features accommodations with access to a sauna.

Mountainview Escape home is located in Killington, just 8.7 miles from Killington Peak and 3.6 miles from Gifford Woods State Park.

8.8 miles from Killington Peak in Killington, Killington A-Frame home offers accommodations with access to a hot tub.

Bob's Sled Lodge offers accommodations in Killington, 8.5 miles from Killington Peak and 3.3 miles from Gifford Woods State Park.

4BR Killington Home Perfect for Families, Pet-Friendly, Fireplace offers accommodations in Killington, 8.4 miles from Killington Peak and 3.3 miles from Gifford Woods State Park.

These cottages in Pittsfield and nearby have options with free cancellation

See all

Perfect secluded 3 bedroom cozy getaway home Hawk Landing is located in Pittsfield, just 13 miles from Killington Peak and 8 miles from Gifford Woods State Park.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

8.7 miles from Killington Peak in Killington, Wonderful One bedroom condo located in Highridge Condominiums J6 features accommodations with access to a hot tub and fitness room.

Skiers Suite 2RM 2BA Renovated Condo 1366

Killington
Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

8.2 miles from Killington Peak in Killington, Skiers Suite 2RM 2BA Renovated Condo 1366 features accommodations with access to a spa center and fitness center.

Private Killington Home with Indoor Hot Tub and 2 Living Rooms offers accommodations in Killington, 7.2 miles from Killington Peak and 2.1 miles from Gifford Woods State Park.

The Sweet Maple Getaway & Maple Welcome Gift! offers accommodations in Rochester, 20 miles from Pico Peak and 27 miles from Mad River.

Holiday Haus AC game room near golf

Killington
Free cancellation options available

Holiday Haus AC game room near golf offers accommodations in Killington, 6.8 miles from Killington Peak and 1.7 miles from Gifford Woods State Park.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Snowarts- Game room, Fireplace, Close to golf offers accommodations in Killington, 6.8 miles from Killington Peak and 1.6 miles from Gifford Woods State Park.

Rustic 3 bedroom home Moose Lodge

Killington
Free cancellation options available

Rustic 3 bedroom home Moose Lodge offers accommodations in Killington, 6.6 miles from Killington Pico Adventure Center and 13 miles from Mclaughlin Falls.

Enjoy breakfast in Pittsfield and nearby

See all
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 1 review

5.7 miles from Killington Peak in Killington, Hot Tub Sauna Firepit Nespresso Huge TV features accommodations with access to a sauna.

Renovated 4BR House - Hot Tub, Game Room & Fire Pit - 11 Mins to Killington Lifts & Dining is located in Killington, just 5.7 miles from Killington Peak and a 11-minute walk from Gifford Woods State...

FAQ about cottages in Pittsfield

On average, a cottage in Pittsfield costs $184 per night (based on Booking.com prices).
The average price per night for a cottage in Pittsfield this weekend is $1,562 (based on Booking.com prices).
The average price of a cottage in Pittsfield this evening is $594 (based on Booking.com prices).