Holiday rentals in Millerton

4.92 out of 5 average rating, 105 reviews

Flat 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.

4.97 out of 5 average rating, 123 reviews

Home in Amenia

The Red Country Cottage

Perfect getaway in this countryside cottage nestled in nature but walking distance to town center. Spend some relaxing time watching the creak run by, walk or bike (provided/bring own) on the 26mi flat scenic Harlem Valley Rail Trail from the cottage. Enjoy the evening sitting by the fire/comfortable patio. Visit the 60’s themed movie theater and restaurant walking distance, near by brewery/winery/cafe/restaurants, wedding venues, Lime Rock Racing, skiing. Direct train to Wassaic from MetroNorth

4.95 out of 5 average rating, 105 reviews

Guest house in Salisbury

Lakeville studio, 2nd floor Near Lake, Limerock AT

Spacious second floor studio. Close to local private schools, Catamount and Butternut ski areas, Limerock park, nearby Berkshires attractions, ski jumps! Short walk to convenience store, several restaurants, a nail salon, gym and package store. There is a laundromat nearby. 1/2 mile to Lake Wonoscopomuc, nearby park and tennis courts, and beautiful walks on rural roads. There are 2 units in this building- this listing is the upstairs, shared entrance but units are separate of each other. Edit

4.98 out of 5 average rating, 104 reviews

Guest house 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, 182 reviews

Flat 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.

4.99 out of 5 average rating, 144 reviews

Flat in Canaan

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

4.93 out of 5 average rating, 154 reviews

Cottage in Cornwall

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

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

4.79 out of 5 average rating, 108 reviews

Flat in Millerton

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.

4.93 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.

4.86 out of 5 average rating, 155 reviews

Cottage in North East

Sunset Cottage: Unplug - Relax - Recharge

Charming country cottage in Millerton, New York with a variety of nearby destinations. Unwind on a quiet country road with cows as your closest neighbors. Use as a base to explore the Tri-State area. Perfect for Parent Weekends for the nearby private schools. An idyllic setting in which to unplug and enjoy nature. Walk to the 42-mile Rail Trail, strap your bikes, skis, kayaks, or canoes to the car because you’ll be centrally located for adventure!

4.96 out of 5 average rating, 334 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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Other great holiday rentals in Millerton

4.95 out of 5 average rating, 99 reviews

The Barn - Rustic Chic Loft, Hotchkiss, Lakes, Ski

SethRating, 5 stars1 month ago

Very comfortable house - nice and airy. Great location just outside Lakeville. Highly recommend.

4.96 out of 5 average rating, 25 reviews

Peace at Last

GraceRating, 5 stars2 weeks ago

This was my family's second time staying at Jennifer's home, and we will be back again soon! The moment you step you, you feel you're in a serene getaway in a lovely cottage. Our host met every need and went above and beyond on flexibility. This is such a gem in Salisbury!

4.96 out of 5 average rating, 24 reviews

“Magical” Brookside Cottage

LuzRating, 5 stars1 month ago

I stayed here for my wedding weekend! The place is beautiful and super spacious, I loved it!! It will remain in my memory forever 🫶🏾

5 out of 5 average rating, 7 reviews

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, 35 reviews

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

ChrisRating, 5 stars5 days ago

Fil & Ellie’s place was the perfect stay for our getaway. Their home is amazing. We were very impressed by the amenities, the cleanliness and attention to detail. This place has everything you’ll need for a great stay. The hosts were also very helpful in answering our questions and assisting us with check-in. I would highly recommend staying here if you have the chance.

4.93 out of 5 average rating, 15 reviews

Stylish getaway in the Berkshires

NedRating, 5 stars2 weeks ago

Bright, light good layout inside and short walk to Salisbury and very short drive to Lakeville. Would definitely stay here again

4.9 out of 5 average rating, 10 reviews

Home in Millerton

Private cabin on five acres close to town

EmilyRating, 5 stars3 months ago

Our group of 6 had a great time at PE's cabin! The place looks nice in pictures, but even better in person. It is uniquely decorated, cozy, and functional. We spent most of our time at skiing Catamount only 20 minutes away, so although had to squeeze a bit for sleeping (still comfortable, but had one guest sleeping on a floor mattress and another on the couch) this was still perfect for our needs as we could all comfortably hang out together in the living room! PE was always quick to answer any questions and gave clear instructions for how to check in. Overall a great place to stay.