Vacation rentals in Ancram

4.92 out of 5 average rating, 105 reviews

A covered front porch features wooden flooring and is framed by dark columns. Two rustic wooden chairs are positioned beside a small table, creating a space for relaxation. Surrounding greenery is visible, enhancing the natural setting.

Apartment in Amenia

Amenia Main St Cozy Studio

Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

Apartment in Copake Falls

A bright and airy living space features a round wooden dining table surrounded by black chairs. Large windows invite natural light, offering views of the scenic outdoor landscape. A seating area with a black sofa is positioned beside a modern fireplace, enhancing the room's comfort.

4.91 out of 5 average rating, 331 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

4.98 out of 5 average rating, 104 reviews

Guesthouse in Millerton

Loft in the Pines

Loft in the Pines: Get away to your own private retreat, walkable to Main St, Millerton, NY & Harlem Valley Rail Trail. Beautiful 1 bedroom escape with two decks for your relaxation. Perfect for couples or families. Close to great hiking & skiing. Easy walk to antique shops & delicious restaurants or put your feet up and relax! 1.5 baths, living room with flat screen TV, dining room & fully equipped kitchen & expansive deck to take in the view. Rent with House in The Pines for a larger group

4.99 out of 5 average rating, 181 reviews

A wooden dock extends over the shimmering water, featuring two Adirondack chairs positioned for serene views. The surrounding natural landscape includes tall grass near the water's edge, enhancing the tranquil setting.

Home in Ancram

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok

All size Dogs & Cats Welcome *Outside backyard is large and surrounded by trees with Firepit, Hammock & Volleyball Net +Watercraft available - Kayaks/Rowboat Swim Platform Indoor Wood Burning Fireplace Fully stocked kitchen and toiletries 10-15 minutes to Bash Bish Falls/Catamount Aerial Park/Ski/Snowboard/Tubing 25-30 minutes to Berkshires Shoe shoeing +November-April: watercraft not available, also weather dependent *Only one neighbor, is to the left, separated by trees and bushes

4.98 out of 5 average rating, 182 reviews

A kitchen area is presented, featuring a microwave and convection oven on a shelf. Blue dishware is arranged above, while cooking utensils hang to the left. A lower shelf holds additional kitchen items. The wall is painted a soft yellow, contributing to a bright environment.

Apartment in Pine Plains

Newly renovated cutie

Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

4.92 out of 5 average rating, 368 reviews

A charming kitchenette is visible, featuring wood-paneled walls and warm lighting from a candle-style wall sconce. Glass doors provide a view of cabinetry and modern appliances, including an induction stove top and convection air fryer toaster oven, ensuring functionality for light cooking.

Guest suite in Red Hook

the farmhouse suite @barn & bike

A 620 sq ft. fully private suite with your own entrance in a beautiful early American eyebrow colonial. The mid-century farmhouse style is highlighted by a darling kitchenette. And don't forget the bathroom hot steam shower! Please note the kitchenette has an induction stove top and convection air fryer toaster oven. It's a great for light cooking. Please ask for a grill for cooking meat and greasy food. We are a zoned b&b with bike rentals. See barn & bike, llc for more info.

4.97 out of 5 average rating, 233 reviews

The A-frame cabin is nestled among tall trees, with warm light spilling from large windows, creating an inviting glow. A winding path leads to the entrance, while surrounding greenery enhances the sense of seclusion and natural beauty.

Cabin in Pine Plains

The Upstate A - Modern Luxury in the Hudson Valley

The Upstate A is a 3 bedroom + sleeping loft, 2.5 bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson Valley. Built in 1968, it was fully renovated in 2020-2021. Staying here you’ll experience a cozy yet modern vibe, immersed in nature but with all the accoutrements of an upscale stay. You'll find great hiking in the summer, skiing in the winter, fresh upstate air year-round and serenity all day and night. See for yourself: check us out on IG @upstate_aframe

Superhost

A modern bathroom is featured, showcasing a walk-in shower with a glass enclosure. A sleek vanity with a dark wooden base holds a white sink. Above, a round mirror is mounted on the wall. Geometric floor tiles add visual interest, complemented by a black shower fixture.

Apartment in Millerton

4.79 out of 5 average rating, 108 reviews

The Studio

Millerton, NY is a weekenders dream! Enjoy a peaceful stay at our newly renovated Studio fully furnished and with a Queen Bed. You’re just a short walk from everything the village of Millerton has to offer! Grab a bite to eat at the popular Oakhurst Diner or indulge in a coffee at Irving Farm Coffee Roasters. After that, make your way to Westerlind to do a little shopping, pop into Oblong Books or enjoy the charm of an old time film theater by checking out The Movie house.

4.99 out of 5 average rating, 137 reviews

A small decorative holiday tree with festive lights and ornaments is positioned on a table. Colorful paper chains adorned with holiday patterns surround the base, complementing a nearby sign that reads 'Most Wonderful of the Year.' A vibrant red table runner adds warmth to the setting.

Cottage in Pine Plains

Pine Plains Cottage

Located just 2 hours north of NYC, our country cottage in bucolic Pine Plains is newly renovated and furnished in a modern yet cozy style, welcoming you to a relaxing retreat! It is located in the heart of Pine Plains, a short walk to the town center. Perfect for 2-4 people. We currently have a 2 night min. stay and 3 night min. for holiday weekends. Contact us directly for week/month/shorter stays and to inquire if we can accommodate your pet or a shorter stay!

4.94 out of 5 average rating, 142 reviews

A bright living area features large windows allowing natural light to fill the space. Wooden beams span the ceiling, while a cozy seating arrangement includes a white couch and a mid-century chair. A patterned area rug enhances the room's inviting atmosphere.

Home in Ancramdale

Unwind in the country, stargaze in hot tub

This peaceful home is in the middle of nowhere, yet conveniently close to it all: Bash Bish Falls (10 mins), Millerton (10 mins), Copake Lake (15 mins), Catamount Mtn (20 mins), Lakeville, Conn. (20 mins), Hudson, NY & Great Barrington, Mass. (30 mins). For those who'd prefer to read by the fire or stargaze from the hot tub, this home is a destination in and of itself. Luxuriously comfortable beds plus all the amenities offer a restful retreat from busy lives.

4.93 out of 5 average rating, 367 reviews

Guest suite in Millerton

Sunset 60 mile view

ROMANTIC LUXURY! Spring has SPRUNG! Gorgeous warm weather; fresh, crisp mountain air. Clear starry nights. Your own private suite, entrance, kitchen, bathroom, outdoor dining facilities, charcoal bar b q grill. Located atop a mountain with magnificent SUNSET view 50 miles overlooking the Hudson River Valley. Completely steam cleaned, disinfected and sterilized before each guest. HEPA Air filters installed. High speed WIFI, 500mbps! 55” 4K HD TV.

4.96 out of 5 average rating, 334 reviews

A wooden sauna is showcased with glass doors, highlighting a spacious interior with wooden benches and a soothing blue light. Natural light filters in through a window, adding warmth to the inviting atmosphere.

Farm stay in Ancram

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

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Other great vacation rentals in Ancram

A bright kitchen features a marble countertop paired with warm yellow cabinetry, complemented by a black stove. A vase filled with white peonies sits on the counter, illuminated by sunlight streaming through a large window overlooking lush greenery.

4.97 out of 5 average rating, 36 reviews

TREE FARM Hilltop Getaway: Majestic Mountain Views

KatherineRating, 5 stars3 months ago

We had a wonderful, restful stay in this beautiful home. The ambience is so peaceful and the home is spotless, with many thoughtful touches for guests. We'd definitely stay again!

An outdoor deck is furnished with a large table surrounded by six cushioned chairs, shaded by a large umbrella. Flower pots adorn the railing and the backdrop consists of lush green trees, enhancing the tranquil setting.

4.94 out of 5 average rating, 82 reviews

Bright/Spacious Getaway at foot of the Berkshires

NaomiRating, 5 stars2 weeks ago

I rented this Airbnb for a crew of horticulture students coming to work on a local project. They needed a nearby comfortable place to relax and rest well from grueling days of work, and each of them came to me separately to say how great their stay was. They had both the privacy of individual bedrooms and wonderful common spaces to meet everyone’s needs.

5 out of 5 average rating, 42 reviews

Home in Gallatin

Hudson Valley Renovated 1860s Farmhouse

CristaRating, 5 stars3 weeks ago

Lovely stay for 3 generations celebrating a Bard graduate. Best beds we have ever slept in. Loved the waterfall in the back. Outdoor and indoor spaces enhanced our experience.

A metal sign is mounted on a red wooden wall, featuring the words 'Yellow Door House' along with a graphic of trees. The sunlight casts shadows on the surface, highlighting the texture of the wood and the sign.

4.92 out of 5 average rating, 66 reviews

Yellow Door House

WiolettaRating, 5 stars1 week ago

Great communicator. Quickly responses. Great place. Thank you!

5 out of 5 average rating, 7 reviews

A gently flowing stream is framed by lush greenery and trees displaying autumn colors. Pebbles and rocks line the water's edge, while fallen leaves float on the surface. The peaceful natural setting invites a sense of tranquility and connection to the outdoors.

Home in Pine Plains

Stunningly Designed Historical Icon w/ Hot Tub

NataliaRating, 5 stars3 months ago

Still gleaming from an unforgettable stay at Willow Vale which is hands down a 5-star gem! The design of the house is one-of-kind where every detail piques curiosity and wonder. The library stole our hearts from the start, brimming with an extensive book collection and unique treasures. We sat by the fire here every night. The sunroom was the perfect daytime spot where we napped, worked, ate and played games. It’s impossible not to fall in love with the kitchen…we cooked almost every meal. Enjoying the hot tub under the stars was a highlight. We loved that there was a telescope and took advantage of it. The river was serene with a perfect swimming hole…and cold plunge! The house is secluded and there is so much to do nearby. It’s truly the land of hidden gems. Stissing House for dinner is a MUST. As their home might suggest, Matt and Whitney go above and beyond as hosts. They made this family vacation special for us in every possible way. We cannot wait to return!!!

5 out of 5 average rating, 18 reviews

Home in Pine Plains

Stony Hill Haus in Pine Plains

MilissaRating, 5 stars2 weeks ago

Stony Hill is beyond our expectations! What an absolutely beautiful home. So many great decorating choices and the kitchen is a baker’s dream. The bedrooms were very comfortable and the grounds are fun to explore with something new around every corner. We didn’t want to leave! Also the town of Pine Plains did not disappoint. Our family including my 80 yo parents, son/his wife & son all slept well there. If ever back in the area we would definitely rent again!

4.95 out of 5 average rating, 22 reviews

Lakeside Haven

NickRating, 5 stars1 month ago

My friends and I had a great time at the Lake House, we really loved being right on the pond and the property was well maintained in and out. Denise is very responsive and had her place set up and provisioned great for a nice weekend stay. The location is also great, close to the Taconic Parkway and a lot of things to do. 10/10!