Vacation rentals in Pittsfield

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Top-rated vacation rentals in Pittsfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Condo in Killington

4.88 out of 5 average rating, 193 reviews

Killington-Pico ski in/out Studio at base of Pico

At the base of Pico and 10 minutes from Killington. Free shuttle service from my place to Killington. I have a free ski locker and free wood for the fireplace. There is a laundry room with coin operated machines. There is a brand new 50” flat screen tv with cable. It’s a smart tv, that’s hooked up to WiFi, so you can use your Netflix, Amazon or Hulu account if you want. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for 1 day. No daily cleaning service. No parties.

Apr. 25 – May 2

$167 CAD per night
Guest favourite

Guest suite in Royalton

4.95 out of 5 average rating, 174 reviews

Private Guest Suite on 155 Acre Royalton Town Farm

1 Bed, 1 Bath apartment attached to historic farm house. This cozy space is the perfect spot for a weekend getaway or a long family vacation on a historic Vermont Farm. Equipped with all the linens and dishes you will need and even a few extras like farm fresh eggs in the fridge and hot chocolate. Close to I-89 and 30 minutes of Ski Resorts like Saskadena Six. Property of 155 acres has trails, sledding hills and our farm animals you can enjoy. Check our reviews, you won't be disappointed!

Apr. 10 – 17

$178 CAD per night
Guest favourite

Chalet in Stockbridge

4.85 out of 5 average rating, 110 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Aug. 28 – Sep. 4

$253 CAD per night

Popular amenities for Pittsfield vacation rentals

Stay near Pittsfield's top sights

Clear River Tavern23 locals recommend
Swiss Farm Inn10 locals recommend
Clear River Inn9 locals recommend
Green Mountain Trails16 locals recommend
Riverside Farm3 locals recommend
The Backroom14 locals recommend

Other great vacation rentals in Pittsfield

Guest favourite

Home in Rochester

4.98 out of 5 average rating, 181 reviews

The Guest House at Sky Hollow

Nov. 20 – 27

$257 CAD per night
Guest favourite

Townhouse in Killington

4.92 out of 5 average rating, 226 reviews

Modern Mountain Condo with Spa, Pool, Sauna, Gym

May 8 – 15

$247 CAD per night
Guest favourite

Tiny homes in Warren

4.99 out of 5 average rating, 146 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Sep. 1 – 8

$902 CAD per night
Guest favourite

Condo in Killington

4.94 out of 5 average rating, 148 reviews

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

Apr. 26 – May 3

$212 CAD per night
Guest favourite

Tiny homes in Pittsford

4.96 out of 5 average rating, 154 reviews

Charming tiny house with great VT location!

Jun. 2 – 9

$185 CAD per night
Guest favourite

Apartment in Rutland

4.96 out of 5 average rating, 514 reviews

Your home away from home

Nov. 26 – Dec. 3

$147 CAD per night
Guest favourite

Home in Rochester

4.98 out of 5 average rating, 123 reviews

Modern Farmhouse on 25 Acres - Superb Views

Dec. 13 – 20

$1,147 CAD per night
Guest favourite

Apartment in Tunbridge

4.93 out of 5 average rating, 215 reviews

Fairview

Oct. 17 – 24

$139 CAD per night
Guest favourite

Cabin in Hancock

4.95 out of 5 average rating, 219 reviews

Hancock hideaway

Apr. 30 – May 7

$238 CAD per night
Guest favourite

Tiny homes in Pittsfield

5.0 out of 5 average rating, 13 reviews

Tiny Home: VT Mountain Cabin

Nov. 25 – Dec. 2

$406 CAD per night
Guest favourite

Home in Pittsfield

4.97 out of 5 average rating, 36 reviews

Hideaway Mountain at Killington

Jan. 22 – 29

$627 CAD per night
Guest favourite

Apartment in Killington

5.0 out of 5 average rating, 12 reviews

Jack S'Bearo - Slopeside at Pico! Shuttle to Killy

Apr. 13 – 20

$200 CAD per night

Quick stats about vacation rentals in Pittsfield

Total rentals

70 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

60 properties are a good fit for families

Total number of reviews

2.6K reviews

Nightly prices starting at

$163 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Rutland County
  5. Pittsfield