Holiday houses in Ancramdale

4.93 out of 5 average rating, 108 reviews

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.

4.92 out of 5 average rating, 119 reviews

Home in Craryville

The Gatehouse at Raspberry Ridge

Quiet, private house for a country get-away. Renovated 2 bedroom, 1 bath home can sleep up to 2 couples. Gated and fenced yard offers privacy and security for children or dogs. Enjoy a spacious deck and sunken fire pit for outdoor dining or lounging. Bedrooms and living space upstairs are bright, airy with cozy wood stove for cool evenings. Kitchen is well-stocked; has a dishwasher. Laundry facilities downstairs; entertainment room with large screen TV and pull out couch. WiFi available.

Apartment in Copake Falls

4.9 out of 5 average rating, 334 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, 105 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

4.98 out of 5 average rating, 184 reviews

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

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

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

Apartment in Millerton

4.79 out of 5 average rating, 109 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.

4.98 out of 5 average rating, 123 reviews

Twin Island Lake House • Hot Tub

Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with private bathroom. Open concept kitchen/living room. A perfect getaway to relax and recharge in our year round 6 person hot tub. Amazing views and sunsets over the lake and mountains. Great area for hiking, fishing, kayaking, canoeing and bird watching. 16 miles to the center of Rhinebeck. Explore the local farms, restaurants, distilleries and wineries.

4.94 out of 5 average rating, 142 reviews

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.

4.92 out of 5 average rating, 370 reviews

Guest suite in Millerton

Sunset, Peace&Quiet, Self check in, 500m wifi

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, 335 reviews

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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5 out of 5 average rating, 53 reviews

Home in Hillsdale

Cambridge Hill Farmhouse - Sauna - Swimming Pond

BekahRating, 5 stars2 days ago

This was such a lovely country escape for us tired city kids. The pond was a beautiful backdrop for reading and drawing. We brought our binoculars and walked across to Dan B road, spotting gorgeous birds multiple times a day. Our host, Danielle, was extremely responsive and friendly. A fuse blew our second night there, and Danielle had an electrician out to fix it the next day so we could sleep with AC that night. One warning: if you're tall, there are some very low ceilings and doorways. My partner is 6'2 and hit his head repeatedly on the bathrooms' vaulted ceilings and the kitchen doorway. The house would be great for a big group, or a family with kids -- the playroom is delightful and the big, fun kitchen makes you want to fill with your friends and eat and talk for hours. We're very grateful for our quiet getaway there!

Superhost

4.85 out of 5 average rating, 33 reviews

Historic Cottage w Brand New Hot Tub and Game Room

MariahRating, 5 stars3 months ago

Fantastic place. All the amenities were exactly what we were looking for. Would definitely stay again.

5 out of 5 average rating, 7 reviews

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!!!

4.97 out of 5 average rating, 62 reviews

Cottage in Pine Plains

The Gallatin Farmhouse

TrishRating, 5 stars1 month ago

Stayed for two nights to attend a wedding nearby. We were only sorry that we did not get enough time to enjoy the house and area more.

5 out of 5 average rating, 25 reviews

Cabin in Craryville

Cabin on Copake Lake, NY.

JoRating, 5 stars3 weeks ago

Great for a weekend away with my friends and I!!! Looks exactly like the pictures and was listed for an AMAZING price for everything that we got! Would totally come back and could not recommend enough!!!

5 out of 5 average rating, 18 reviews

Stony Hill Haus in Pine Plains

MilissaRating, 5 stars3 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!

4.88 out of 5 average rating, 25 reviews

Apartment in Red Hook

Secluded hideaway gem

ValeriyaRating, 5 stars2 days ago

Incredibly thoughtful hosts, who have made the place feel at home as soon as you walk in. The bed was witchy - I can’t remember having such a cloud nine rest and beautiful dreams sleeping not in my bed. Rooms were spotless and pristine. Overall very home-felt feeling. It made me sad to leave the place. Highly recommending, especially to those seeking to have a “retreat” and rejuvenating time, and don’t miss the sunrises on the premises.