Book Holiday Homes in Pittsfield
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Featured Holiday Homes in Pittsfield

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

Stargazer's retreat with hot tub & decks - near Ellacoya State Beach

Stunning 5 BR Lakefront Home with Private Gym & Boat House

Idyllic Mountain and Lake Getaway

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Waterfront home with wraparound deck, floating fireplace, deck, & firepit

Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area

3-bedroom + double futon, 2 bath house in Laconia, 1 mile from Lake Winnisquam!
Pittsfield Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Pittsfield vacation homes are the perfect way for you to wing it.
Holiday houses in Pittsfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Pittsfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Pittsfield adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Pittsfield with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Pittsfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Pittsfield Holiday Homes essential information
Accommodation | 400 Holiday Homes |
|---|---|
Lowest Price | AU$128 |
Highest Price | AU$1,065 |
Popular accommodation | Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski, Stargazer's retreat with hot tub & decks - near Ellacoya State Beach, Stunning 5 BR Lakefront Home with Private Gym & Boat House, Idyllic Mountain and Lake Getaway, Perfect Modern Lake Front Retreat with Dock! Sleeps 4, Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!, Waterfront home with wraparound deck, floating fireplace, deck, & firepit, Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area, 3-bedroom + double futon, 2 bath house in Laconia, 1 mile from Lake Winnisquam! |
Top trending hotels in Pittsfield

The Centennial

Winnisquam Lake Inn

Hampton Inn by Hilton Concord/Bow

Microtel Inn & Suites by Wyndham Dover
More ways to explore Pittsfield
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
