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.
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
Cottage in Brandon
4.91 out of 5 average rating, 268 reviewsHenrietta’s Hideaway-Walk Downtown!
Tiny home in Warren
4.99 out of 5 average rating, 167 reviewsLuxury Glass Tiny House - Mountain View + Hot Tub
Home in Middlebury
4.99 out of 5 average rating, 361 reviewsNice one bedroom cottage
Guest suite in Weybridge
4.99 out of 5 average rating, 249 reviewsBeautiful 1 Bedroom Suite with private entrance
Condo in Killington
4.88 out of 5 average rating, 208 reviewsKillington-Pico ski in/out Studio at base of Pico
Cottage in Windsor
4.97 out of 5 average rating, 327 reviewsOgden's Mill Farm
Cabin in Hancock
4.95 out of 5 average rating, 221 reviewsHancock hideaway
Tiny home in Pittsfield
5.0 out of 5 average rating, 21 reviewsTiny Home: VT Mountain Cabin
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.
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