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

This farmhouse has stood here since 1705, and it shows its age without hiding it. Original floors, restored vintage furniture, Farrow & Ball walls, a historic barn out back. We've looked after it and updated what needed it, so it feels as good after a day on the trails as it does on a morning with nowhere to be.

Three private acres open onto 400 acres of Cranberry Mountain State Land: hiking, hunting, and cross-country skiing from the property line. Inside, there's a fire going.

boots off, fire on

Read a Note From Us

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, or full time

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 is less than a mile from our front door, an hour north of Manhattan and twenty minutes from Danbury. Gentle slopes for beginners, night skiing, a lodge with hot chocolate.

Ski in the morning, spend the afternoon by the fire, and skip the Vermont traffic. For a full ski season, it's a winter base five minutes from the lifts and an hour from New York City.

hot chocolate is mandatory

Summer

The Appalachian Trail Runs Through the Neighborhood

Pawling has the only train station on the entire Appalachian Trail, and some of the best day hiking within an hour of New York City starts here. Walk out the door into Cranberry Mountain State Land and find the waterfall. 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, there are three acres to run, farm visits down the road, and a porch that becomes 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
“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 bakeries, restaurants, and the train station.

✿

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 for a Season, or Full Time

Winter Season

From $6,500

Per Month · Flexible Start, Through April

Summer Season

From $7,250

Per Month · May Through October

Full Time

Let's Talk

Lease Length and Start Date Are Flexible

The house comes furnished, one household at a time, by the season or full time. We're flexible on lease length and start date, so send us a note or book on Airbnb.

two seasons, your choice

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

We host one household at a time, winter, summer, or full time. Tell us what you have in mind and we'll send what is open. We're flexible on lease length and start date.

Booked Directly With the Owners

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Ready When You Are

The house is yours for a full season. Book on Airbnb or send us a note.

Book Now on Airbnb Inquire for a Season