Vacation rentals in Pittsfield

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Top-rated vacation rentals in Pittsfield

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Guest favorite

Condo in Killington

4.89 out of 5 average rating, 203 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.

May 14 – 21

G$20,751 GYD per night

Guest favorite

Guest suite in Royalton

4.96 out of 5 average rating, 180 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!

Jun 24 – Jul 1

G$24,549 GYD per night

Superhost

Chalet in Stockbridge

4.85 out of 5 average rating, 114 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 27 – Sep 3

G$32,782 GYD per night

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 129 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

Aug 6 – 13

G$20,762 GYD per night

Guest favorite

Townhouse in Killington

4.93 out of 5 average rating, 231 reviews

Modern Mountain Condo with Spa, Pool, Sauna, Gym

Escape from your suburban home and come enjoy our beautiful Killington getaway condo. Boasting a spacious, comfortably furnished interior, this modern 2-bedroom, 2-bathroom abode is perfect for families, multiple couples, or a romantic getaway. Our Killington Air BNB has far more than the average Air BNB with everything you need for a great experience. If you're working during your stay you'll find high speed wifi and a dedicated desk space so you can focus on business when not on the slopes

May 13 – 20

G$29,582 GYD per night

Guest favorite

Tiny home in Pittsford

4.96 out of 5 average rating, 155 reviews

Charming tiny house with great VT location!

Curious about tiny home living!? This newly constructed 180 sq ft. house will let you experience comfort in charming farmhouse/cottage style. (Shiplap walls anyone?) Only 25 min to Killington, and 12 min from Mtn Top Inn, Downtown Rutland, or Brandon VT makes the location very convenient. Situated on over 2 acres of private back yard, overlooking beautiful Sugar Hollow Brook in the heart of Pittsford, Vermont. Walking distance to village general store, library and the Pittsford trail system.

Jun 10 – 17

G$24,912 GYD per night

Guest favorite

Apartment in Chittenden

5.0 out of 5 average rating, 223 reviews

Vermont Country Suite

Located in Chittenden, VT, we are in the heart of the Green Mountains. We are just down the road from the Mountain Top Inn wedding venue and Cross Country Skiing Center. The apartment is an easy 15-20 minute drive to Pico and Killington ski areas. The suite is perfect for winter and summer adventuring or just a quiet get away in Vermont. * We are following the guidelines set up by the W.H. O. and we are leaving a window between reservations to disinfect our suite due to Covid-19.

Mar 6 – 13

G$26,976 GYD per night

Guest favorite

Apartment in Pittsford

4.99 out of 5 average rating, 117 reviews

Waterfront cottage walk-out suite.

Private entrance suite overlooking Burr Pond. Conveniently close to Mountain Top Inn & Resort (3.7 miles), Killington/Pico ski resorts and Rutland. Swim, kayak, bike and hike in the warmer weather. Take advantage of more than 12 miles of the Pittsford Trail Network. The serenity of country living coupled with the amenities of Rutland! We’re on a short dirt road off of a steep hill. Front wheel or 4 wheel drive vehicles with good all season or snow tires required in the winter.

May 14 – 21

G$22,481 GYD per night

Guest favorite

Cabin in Hancock

4.95 out of 5 average rating, 220 reviews

Hancock hideaway

Skiing, snow biking 10 minutes away at Middlebury Snow Bowl and Rikert crosscountry. Sugarbush and Killington half hour drive. Snowshoeing and hiking right behind house in the Green Mountain National Forest. Easy drive to river swimming holes and lakes. Excellent restaurants in Waitsfield and Middlebury - about half hour. Good restaurant, cafe, small grocery store, in Rochester, 4 miles. Great location, beautiful views, lovely little house, totally private, romantic.

May 14 – 21

G$30,493 GYD per night

Guest favorite

Home in Pittsfield

4.91 out of 5 average rating, 149 reviews

Beautiful Mountain Log Cabin with Scenic Views

A unique post and beam log cabin with beautiful scenic mountain views. 15 minutes from killington and pico ski areas. This one of a kind house offers an open floor plan with a great room and fireplace. Master suite has its own fireplace, jacuzzi tub and balcony. A loft area with pool table and tv . Outside hot tub with mountain views. Two car garage to park in on cold snowy nights. Large basement off garage makes getting out of your ski gear easy.

Jul 7 – 14

G$75,996 GYD per night

Guest favorite

Cabin in Rochester

4.95 out of 5 average rating, 391 reviews

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Dec 5 – 12

G$29,075 GYD per night

Guest favorite

Apartment in Rutland

4.96 out of 5 average rating, 522 reviews

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

Nov 19 – 26

G$20,675 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Pittsfield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Pittsfield's top sights

Clear River Tavern23 locals recommend

Clear River Inn9 locals recommend

Swiss Farm Inn10 locals recommend

Green Mountain Trails16 locals recommend

Riverside Farm3 locals recommend

The Backroom14 locals recommend

Other great vacation rentals in Pittsfield

Guest favorite

Guest suite in Bethel

4.97 out of 5 average rating, 137 reviews

Two bedroom. Separate enterence.

Aug 25 – Sep 1

G$28,633 GYD per night

Guest favorite

Home in Rochester

4.97 out of 5 average rating, 182 reviews

The Guest House at Sky Hollow

Sep 8 – 15

G$33,666 GYD per night

Guest favorite

Home in Bethel

4.84 out of 5 average rating, 129 reviews

Hike, run, swim or cycle in beautiful Central VT

Oct 20 – 27

G$26,904 GYD per night

Guest favorite

Cabin in Royalton

4.99 out of 5 average rating, 174 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

Jan 3 – 10

G$32,287 GYD per night

Guest favorite

Cabin in Hancock

4.97 out of 5 average rating, 343 reviews

Funky, family-friendly cabin

Nov 18 – 25

G$34,513 GYD per night

Guest favorite

Condo in Killington

4.81 out of 5 average rating, 140 reviews

1BR Modern Condo @ Whiffletree Ground Fl Walkout

May 16 – 23

G$17,962 GYD per night

Guest favorite

Cabin in Vershire

4.99 out of 5 average rating, 188 reviews

Comfortable cozy cabin in the hills of Vermont!

Feb 9 – 16

G$23,943 GYD per night

Guest favorite

Guest suite in Castleton

4.98 out of 5 average rating, 119 reviews

Mi Casa es su Casa!

Oct 27 – Nov 3

G$23,748 GYD per night

Show all

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
2.8K reviews
Nightly prices starting at
G$25,018 GYD before taxes and fees

Frequently Asked Questions

Do house rentals in Pittsfield have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Pittsfield have wifi?
Absolutely! We offer over 30 house rentals with wifi in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Pittsfield?
Yes! Work meets play with ease at over 30 vacation rentals in Pittsfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Pittsfield have free parking?
Absolutely! We offer over 30 house rentals with free parking in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Pittsfield?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a kitchen, over 30 homes with free parking, over 30 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Pittsfield?
Four-legged friends are welcome in Pittsfield. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Pittsfield?
Pittsfield has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Pittsfield have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Pittsfield. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Pittsfield

Top-rated vacation rentals in Pittsfield

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Pittsfield vacation rentals

Stay near Pittsfield's top sights

Other great vacation rentals in Pittsfield

Guest suite in Bethel

Home in Rochester

Home in Bethel

Cabin in Royalton

Cabin in Hancock

Condo in Killington

Cabin in Vershire

Guest suite in Castleton

Quick stats about vacation rentals in Pittsfield

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Pittsfield have a kitchen?

Do house rentals in Pittsfield have wifi?

Are there vacation rentals with a dedicated workspace in Pittsfield?

Do house rentals in Pittsfield have free parking?

What are the most popular amenities for House Rentals in Pittsfield?

Are there pet-friendly vacation rentals in Pittsfield?

Are there family-friendly vacation rentals in Pittsfield?

Do house rentals in Pittsfield have air conditioning?

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