
Holiday rentals with a patio in Pittsfield
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Top-rated rentals with patio in Pittsfield
Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.
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Popular amenities for rentals with patio in Pittsfield
Flat rentals with a patio

Apartment B, Historic building
Third time staying and would highly recommend. Peggy is an amazing host making things easy. Feels like a second home to us!

River's Bend NEW 1-bd Apt - 8 Mins to Montpelier
My wife and I wanted to find a place to stay for a few nights to ski. Ted’s place was perfect. He was incredibly responsive when we had questions. Great stay overall.

Cozy two bedroom near Manchester
Had a great stay here! It's a lovely, cozy spot, and Ivor was very responsive and helpful. It was exactly what we were looking for! Note for taller guests: as this is a top floor apartment, the sides of the ceilings are angled, so watch your head. I highly recommend this place!

Cozy Green Mountain Village Apt
That was perfect house..Thanks

Little City Brick Apartment B
Curtis was an awesome host. The place is cozy and very welcoming. Would definitely stay again if I return.

Mountain View Retreat
Andrew’s place was exactly as described. Just far enough out of of the middle of Middlebury to be completely peaceful, but a very quick drive to town. The space was clean, spacious and had a great kitchen. The view off of the back deck was fabulous. I’d definitely stay there again.

Modern camp-style apartment - self checkin
Great place to stay near Killington. The space in the kitchen/dining area was a little bit tight, 6 people can't eat at the same time. The beds and room were ample in space. The host was very responsive and communicated very well. Will come back if available next time.

Cozy/Private, close to hospital, i-89
This was such a beautiful rental and so peaceful. The views were amazing and the house and giant yard were extremely child friendly, including a play area inside and outside. The beds were super comfy and the host was so friendly. The amenities were great especially the coffee counter. Definitely will stay there again and recommend it to anyone looking for a stay that feels like a home away from home.
House rentals with a patio

Stay by the Mettawee
Such a beautiful home! Great kitchen for cooking and cozy living room perfect for watching movies. Enjoyed our stay very much.

Waitsfield Post and Beam Home
Very comfortable stay in a beautiful setting.

Mountain View Getaway
Beautiful home in the mountains! We enjoyed the breathtaking view and loved that it was only about 15 minutes from downtown Manchester. Great get away!

6 Bedroom Home Mendon, VT. (Killington/Pico)
This is our third (or fourth?) year staying here and they keep adding little things to make it better. Host is very responsive. House matches the description, and the price is right! Plus we were able to add another night onto our stay at the last minute which was really helpful.

Lake Champlain Waterfront House Retreat
Our family of five just spent Thanksgiving at the lake house. Its size and layout accommodated us well - having the second frig became necessary. It’s a lovely place and stunning views from almost every window. Would definitely come again. Thanks!

Benton House, Sleeps 10, King Bed Primary
We had a great stay! The layout was just perfect for our group with lots of different spaces for us to spread out and a wonderful dining room and kitchen to share preparation and meals together at the end of each day! The location worked perfectly as we were in town for the NCAA Championships being held at Dartmouth . Hoping we can return again when we are back in the area! Friendly and super responsive host!!

Rockwell Haus: modern cabin 14 min from Killington
Beautiful home in peaceful serenity of the woods at the top of the hill. Exceeded all our expectations and the hosts were incredibly accommodating. Super easy access to Killington and a great big open concept kitchen and family room to enjoy meals. Ample room for kids to have their own tv downstairs and games and keep the noise down there. We love the fireplaces on each floor and all the natural light throughout. The house is immaculate with higher end amenities that we really appreciated. The coffee was out and the hosts literally brought us two fresh bags! This house stay made our family ski weekend fun and stress free. We hope to return!

The Little House
We loved staying at Andrea's for our Middlebury reunion! The place was bright and had a great location. Andrea was especially communicative, thoughtful and kind.
Apartment rentals with a patio

Main St Escape | Explore Downtown Ludlow
Clean, great location, easy check in/out, and friendly host - would definitely stay again.

Skiers Paradise @ Sugarbush! Updated 2B/2B
The condo was very cozy, clean and easy to navigate. Beds were comfortable and the easy access to Sugarbush shuttle was ideal!

Killington Condo-Indoor Pool/HotTub/FitnessCenter
Great place for our ski weekend! Spacious, clean, super comfortable beds, kitchen had everything needed, even spices! close easy drive to slopes! Great host- it was easy to communicate, we felt really welcome in this beautiful place! Would love to come back again and again!

Killington Mnt Escape Ski/Golf/Bike/Hike/Pool
It was a pleasure staying at Shirley's place for our last trip to Killington this season. The place was nice and clean, the kitchen had everything we needed to cook our meals, and the amenities in the building were great!

Ski, Hike & Bike Basecamp Condo
We noticed this listing at first mostly due to its location. The condo is close to multiple Mad River Valley ski locations and it is near friends of ours that live locally in Vermont. Once we got there however, we realized that the condo is perfect for our family of four. The place was super clean and comfortable and gave us a nice place to eat/sleep before heading out for the day. The hosts were super responsive and proactive communicating rules and instructions for use of the place. Would highly recommend and would certainly consider staying again.

CozyCub - Pool, Hiking, Mountain Biking
What a great spot. Loved the Murphy bed- many other places have sofas but the Murphy bed is way better.

Christian Street Condo with Screened In Balcony
Team ECEA was required to stay in the West Lebanon area for an extended period of time. We were able to stay at 3 different locations hosted by Wolter Group and each space was just what we needed and very convenient to the location we were working. They were always very responsive and and were a pleasure to do our business with.

Lovely 1-Bedroom condo with indoor fireplace!
Such an amazing place. Great location for walking to restaurant. Breath taking views especially the river. Extremely homey feel. We will definitely be back. thank you for your hospitality.
Quick stats about holiday rentals with a patio in Pittsfield
Total rentals
50 properties
Nightly prices starting at
£89 before taxes and fees
Total number of reviews
2.5K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Baker Hill Golf Club
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- Country Club of Vermont
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
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- Mount Sunapee Resort
- Whaleback Mountain
- Storrs Hill Ski Area
- Killington Adventure Center
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- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery