Farmhouse Rental Near Pawling, New York: The Little Red Farmhouse since 1705

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A restored 1705 farmhouse near Pawling, New York. One hour from the city, five minutes from the slopes, steps from 400 protected acres.

Book Now Inquire About a Stay See Seasons & Rates

The Story

Three Centuries on This Hillside

The farmhouse has stood here since 1705, and it wears its age beautifully. Original floors, restored vintage furniture, walls in Farrow & Ball, and a historic barn out back. Everything has been kept with care and updated where it counts, so the house feels as good to come home to after a day on the trails as it does on a morning with nowhere to be.

Outside, three private acres open onto 400 acres of Cranberry Mountain State Land, with hiking, hunting, and cross-country skiing right from the property line. Inside, there is a fire going.

boots off, fire on

Cathedral beamed great room of the historic 1705 farmhouse rental near Pawling NY
Kept like an editorial spread
Living room with a lit stone fireplace in the Hudson Valley farmhouse rental

Inside the Farmhousecome in, warm up

The House

Room for Six, Designed for Cozy Mornings

Sleeps

6 guests

Bedrooms

3 · two queens, two twins

Baths

3.5 · one for every bedroom

Built

1705

The Land

3 private acres & historic barn

Offered

Winter & summer seasons

Fully furnished and ready for your season in the country.

The Kitchen & Coffee Bar

Breville espresso machine · full kitchen with dishwasher, stove & oven · refrigerator & freezer · air fryer · SodaStream · blender, toaster & kettle · cooking basics, dishes & wine glasses · dining table

Bed & Bath

Every bedroom with its own bath · linens, towels & extra blankets · free washer & dryer · shampoo, conditioner & body soap · hair dryer · iron & hangers · clothing storage

Warmth & Comfort

Multiple indoor fireplaces · central heating · central air conditioning · books & reading material · board games

Work & Stream

Fast wifi · dedicated workspace · HDTV with Netflix & Prime Video

For the Kids

Pack ’n play travel crib · children’s books & toys · gentle beginner slopes five minutes away · backyard snowman territory in winter · firefly catching in summer

Outdoors & Arrival

Covered front porch · backyard & outdoor dining · mountain and valley views · direct trail access to 400 acres of state land · use of the barn · mudroom-friendly entry · free driveway parking · self check-in keypad · long term stays welcome · smoke & CO alarms, first aid kit, exterior security cameras

Winter

Four poster bedroom with a wood burning fireplace, winter ski stay near Thunder Ridge
Back from the slopes by three

The Closest Skiing to New York City Is Five Minutes Away

Thunder Ridge Ski Area sits less than a mile from the front door, an hour north of Manhattan and twenty minutes from Danbury. It is the easiest family ski weekend in the region: gentle slopes for beginners, night skiing, and a lodge with hot chocolate.

Teach the kids to ski in the morning, come back to a fireside afternoon at the farmhouse, and never sit in Vermont traffic. For a full ski season, the house makes an unbeatable winter base near New York City.

hot chocolate is mandatory

Summer

The Appalachian Trail Runs Through the Neighborhood

Pawling is home to the only train station on the entire Appalachian Trail, and some of the best day hiking within an hour of New York City starts right here. Walk out the door into Cranberry Mountain State Land, find the waterfall, or drive ten minutes to the AT boardwalk across the Great Swamp and the climb to Cat Rocks.

In fall, the hunting on the surrounding state land is as good as the foliage. Year round, the kids have three acres to run, farm visits down the road, and a porch that turns into the best seat in the house by dinnertime.

fireflies at eight, porch by nine

Dining room at golden hour in the upstate New York farmhouse rental
Dinner at golden hour
The farmhouse porch and surrounding land

The Landthree acres and four hundred more

★ 5.0 From Our Guests

“Each room is so carefully decorated, like a magical world. The house has clearly been lovingly restored, with all the old charm you could want.”Cc · Delray Beach, Florida
“Such a cute storybook place. Wish we could have had more time there to explore the trails.”Heather · Raleigh, North Carolina
“All the charm of country living mixed with modern amenities. We loved being near the ski area and Pawling’s main street. We’ll be back!”Jessica · Sherman, Connecticut

The Area

Our Favorite Corners of Pawling and Beyond

The village of Pawling is ten minutes away, with everything a weekend or a whole season needs.

✿

Cranberry Mountain State Land

Four hundred acres of protected forest for hiking, hunting, and cross-country skiing. The trails start at our property line.

Out the door

✿

Thunder Ridge Ski Area

The closest ski area to New York City, with night skiing and a ski school.

Next door · 5 min

✿

McKinney & Doyle

The Pawling institution: bakery by day, a proper dinner at night.

Pawling Village · 10 min

✿

Sunflour Bakery

Morning pastries and coffee on Broad Street.

Pawling Village · 10 min

✿

Daryl's House Club

Daryl Hall's live music club and restaurant: dinner and a show.

Route 22 · 10 min

✿

Dykeman Farm

The farm stand for corn, sunflowers, and pumpkin season.

Pawling · 12 min

See the Full Guide: Things to Do Near Pawling, NY

Skiing Near NYC · Appalachian Trail by Train · Seasonal Rentals

Rates & Seasons

Stay a Few Nights or a Season

Winter Season

From $7,250

Per Month · November Through April

Summer Season

From $6,500

Per Month · May Through October

Nightly

From $675

Per Night · 3 Night Minimum

Seasonal stays come fully furnished for the winter and summer seasons. Nightly stays welcome with a three night minimum. Book on Airbnb or inquire for availability.

your season starts here

Getting Here

One Hour From Grand Central

72 miles from Manhattan by car, about an hour up the Saw Mill and 684. The Metro North Harlem Line runs to Patterson and Pawling, and on winter weekends a shuttle connects Patterson station to Thunder Ridge. On summer weekends the train stops directly on the Appalachian Trail.

New York City

1 hr

White Plains

35 min

Danbury, CT

20 min

Thunder Ridge

5 min

Inquire

Ask About Dates

For a season, the farmhouse hosts one household at a time. For shorter stays, three nights or more. Tell us your dates or the season you have in mind and we will send availability and full details.

Booked Directly With the Owners

Ready to Book?

Reserve your dates on Airbnb or send us an inquiry for seasonal stays.

Book Now on Airbnb Inquire for a Season