Vacation rentals in Pittsfield
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Pittsfield
Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield vacation rentals
Other great vacation rentals in Pittsfield
Condo in Killington
4.81 out of 5 average rating, 141 reviews1BR Modern Condo @ Whiffletree Ground Fl Walkout
Condo in Killington
4.88 out of 5 average rating, 208 reviewsKillington-Pico ski in/out Studio at base of Pico
Guest suite in Castleton
4.98 out of 5 average rating, 135 reviewsMi Casa es su Casa!
Home in Pittsfield
4.93 out of 5 average rating, 41 reviewsHideaway Mountain at Killington
Home in Pittsfield
5.0 out of 5 average rating, 3 reviewsRomantic cozy retreat near Killington Mtn
Tiny home in Pittsfield
5.0 out of 5 average rating, 21 reviewsTiny Home: VT Mountain Cabin
Condo in Killington
4.96 out of 5 average rating, 72 reviewsDogs Welcome! - Outdoor Pool/Hot Tub/Hiking
Guest suite in Stockbridge
5.0 out of 5 average rating, 85 reviewsStudio Suite with Vermont Style & Amazing Views
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
$120 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 10 homes with air conditioning, over 30 homes with wifi, 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.
Destinations to explore
- Burlington Vacation rentals
- Lake George Vacation rentals
- Lake Placid Vacation rentals
- Stowe Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Québec Vacation rentals
- Québec City Vacation rentals
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes