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Family-friendly vacation rentals in Pittsfield

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Pittsfield

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Chalet in Stockbridge

4.93 out of 5 average rating, 168 reviews

Killington spring ski - MTbike -new jacuzzi

Killington Ski Area with access to snowmobile and mountain biking trails. This is a 3 bedroom, 2 bath upper unit duplex. with outdoor Jacuzzi open year round with barbecue on very nice decks for those nicer days , snow mobile right from the house , on the tweed valley vast trails , in the summer mountain bike on the green mountain trail system right on our mountain keep us in mind for the summer event like the spartan race and the peak series Mt biking events too Fantastic unit check our review

May 8 – 15

$365 CAD per night

Guest favourite

Guesthouse in Woodstock

4.98 out of 5 average rating, 206 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED. ZERO CONTACT WITH OWNERS.

Dec. 11 – 18

$250 CAD per night

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.

Oct. 2 – 9

$255 CAD per night

Guest favourite

Cottage in Lincoln

4.87 out of 5 average rating, 857 reviews

The Barn at North Orchard, Near Middlebury

Our barn sits on an 80 acre estate with fab views of the Green Mts. near Middlebury/Burlington. Perfect for 2 adults and a child or grandparents/ 2 friendly couples. Close to skiing, hiking, lake & river swimming, great restaurants... local beer, wine, cheese!. Want yoga, pasta class, or massage? We will gladly hook you up. Or, you could stay in to read, work, and enjoy the serenity of the mountains. A very private garden patio for morning coffee/ afternoon beer or wine or awaits you.

Apr. 8 – 15

$188 CAD per night

Guest favourite

Guesthouse in Granville

4.9 out of 5 average rating, 785 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Near Lk George, Lk Champlain, Saratoga, Manchester & Rutland, VT. Hiking, fishing and swimming nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive recommended in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Oct. 24 – 31

$152 CAD per night

Guest favourite

Guest suite in Royalton

4.96 out of 5 average rating, 165 reviews

Bluestone Farm

Bluestone Farm is a private second story guest suite with all the amenities. High ceilings, quiet, on a Vermont back road with 70 plus acres of land and a pond. You have a full working kitchen; private bathroom with large walk in shower; living room, and private bedroom with a queensize mattress. Nearby to Vermont Law School, 40 minutes to Ben and Jerry's, Woodstock, and Montpelier. 2 miles from Worthy Burger and a quick ride to Interstate 89 for many other Vermont attractions.

May 1 – 8

$161 CAD per night

Guest favourite

Cabin in Hancock

4.95 out of 5 average rating, 221 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 3 – 10

$242 CAD per night

Guest favourite

Home in Rochester

4.97 out of 5 average rating, 182 reviews

The Guest House at Sky Hollow

This quiet hilltop house on an 1800's farm turned homestead at the end of a dirt road offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Nov. 11 – 18

$261 CAD per night

Guest favourite

Cabin in Hancock

4.97 out of 5 average rating, 343 reviews

Funky, family-friendly cabin

Our funky, fun house is nestled in the woods, with a waterfall and brook rushing by outside the large wall of windows. Situated in the Green Mountains, this is the perfect place to relax and play. The large open-floor plan is perfect for families with school-age children. Families with infants and toddlers may not find our home as friendly, as the waterfall, loft and attached farm buildings may create some safety challenges.

Mar. 26 – Apr. 2

$262 CAD per night

Guest favourite

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. 6 – 13

$149 CAD per night

Home in Rochester

4.9 out of 5 average rating, 282 reviews

Mountain Home ready for you!

Get away from it all in a secluded home atop a mountain in the VT National Forest. Home with large deck and panoramic view of the Green Mountains. Idyllic in all seasons. Summer is lusciously green; fall colors seen from our deck; the magic of winter. Tons of privacy, but minutes from lovely town of Rochester. Tubing and swimming holes nearby, tons of hiking and biking trails and berry picking nearby.

Jun. 10 – 17

$373 CAD per night

Guest favourite

Cabin in Warren

4.93 out of 5 average rating, 359 reviews

Cabin in the Woods

This cozy cabin is on a well maintained town (dirt) road a short walk to Blueberry Lake (on National Forest land, non-motorized) and is within 15 minutes of Breadloaf Wilderness Area, Sugarbush Ski Resort, Mad River Glen Ski Area, restaurants and dining, arts and crafts, sports and specialty shops. It's wooded, quiet, has a light open feeling inside.

Dec. 21 – 28

$188 CAD per night

Vacation rentals for every style

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Popular amenities for Pittsfield family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Pittsfield

4.83 out of 5 average rating, 221 reviews

Killington area home - 4-seasons & hot tub

Oct. 27 – Nov. 3

$433 CAD per night

Condo in Killington

4.77 out of 5 average rating, 282 reviews

Serene Killington Condo (resort style amenities)

Jul. 4 – 11

$219 CAD per night

Guest favourite

Yurt in Randolph

4.96 out of 5 average rating, 385 reviews

4 Season Lower Yurt Stay on VT Homestead

Nov. 11 – 18

$105 CAD per night

Guest favourite

Chalet in Killington

4.9 out of 5 average rating, 159 reviews

Close to Mountain and walk to restaurants!

Jul. 1 – 8

$364 CAD per night

Home in Killington

4.88 out of 5 average rating, 215 reviews

Tanglewood Vista Ski Home: Close|Hot Tub|Sauna|BBQ

May 10 – 17

$548 CAD per night

Guest favourite

Condo in Killington

4.97 out of 5 average rating, 116 reviews

#45 Mountain Ski & Summer Condo with Private Sauna

Oct. 4 – 11

$660 CAD per night

Guest favourite

Chalet in Killington

4.82 out of 5 average rating, 234 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

Jan. 4 – 11

$1,356 CAD per night

Guest favourite

Home in Addison

4.95 out of 5 average rating, 198 reviews

Brthtkng New Premier Lake Champlain Wfrnt Escape!

Jan. 4 – 11

$344 CAD per night

Family- and pet-friendly home rentals

Guest favourite

Guesthouse in Springfield

4.86 out of 5 average rating, 321 reviews

Connecticut River-Cozy Cottage

Apr. 20 – 27

$143 CAD per night

Guest favourite

Guesthouse in Hartland

4.95 out of 5 average rating, 912 reviews

Yurt In The Woods - Private Refuge

Mar. 22 – 29

$220 CAD per night

Guest favourite

Cabin in Bethel

4.94 out of 5 average rating, 386 reviews

Rustic and Cozy Vermont Getaway at Sugarwood Cabin

Apr. 12 – 19

$292 CAD per night

Guest favourite

Home in Rochester

4.94 out of 5 average rating, 181 reviews

The McKinley House

Jan. 10 – 17

$520 CAD per night

Guest favourite

Home in Granville

4.95 out of 5 average rating, 107 reviews

Epic Views of the Green Mountains

Guest favourite

Guesthouse in Norwich

4.93 out of 5 average rating, 171 reviews

Vermont Log Guest Home-Close to Dartmouth

Jul. 11 – 18

$281 CAD per night

Guest favourite

Apartment in Andover

4.98 out of 5 average rating, 386 reviews

Private Hilltop farm apartment

Sep. 25 – Oct. 2

$175 CAD per night

Guest favourite

Guesthouse in Groton

4.98 out of 5 average rating, 246 reviews

Groton Forest Retreat

Jan. 11 – 18

$178 CAD per night

Family-friendly home rentals with a pool

Guest favourite

Condo in Killington

4.92 out of 5 average rating, 392 reviews

April open 1 bedroom 1 night Ok Free shuttle

Sep. 19 – 26

$230 CAD per night

Guest favourite

Guest suite in Killington

4.95 out of 5 average rating, 139 reviews

Cozy, private, spacious, 3 bedrooms, 5 mi to K Rd.

May 10 – 17

$335 CAD per night

Guest favourite

Condo in Killington

4.82 out of 5 average rating, 250 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

Feb. 19 – 26

$560 CAD per night

Guest favourite

Cabin in Bridport

4.92 out of 5 average rating, 133 reviews

Champlain Valley Alpacas

Apr. 6 – 13

$258 CAD per night

Guest favourite

Apartment in Barre

4.94 out of 5 average rating, 156 reviews

Relax in Recreation Paradise!

Sep. 5 – 12

$229 CAD per night

Guest favourite

Guesthouse in Ticonderoga

4.99 out of 5 average rating, 197 reviews

Chilson Brook Alpacas

Feb. 2 – 9

$472 CAD per night

Guest favourite

Condo in Killington

4.86 out of 5 average rating, 107 reviews

Summer rental - Near Resort 4 Bedroom - Pool

Jun. 5 – 12

$596 CAD per night

Apartment in Mineville

4.74 out of 5 average rating, 122 reviews

Adirondacks getaway w/ Glassblowing Studio

Jun. 14 – 21

$146 CAD per night

Quick stats about vacation rentals that are family-friendly in Pittsfield

Total rentals
60 properties
Wifi availability
60 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
2.3K reviews
Nightly prices starting at
$164 CAD before taxes and fees

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