Holiday rentals in Millbrook

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Top-rated holiday rentals in Millbrook

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Guest favourite
A cozy studio space features a full-size bed with a neutral comforter, a desk and chair set against a wall, and a small television mounted above a radiator. Natural light enters through a window, with patterned curtains framing the view. The bathroom doorway is visible in the background.
Flat in Amenia
4.93 out of 5 average rating, 123 reviews

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.

Guest favourite
A historic farmhouse is set among vibrant greenery and blooming orange flowers. The expansive front porch features classic white railings and is lined with hanging planters. The structure is nestled between two large trees, providing a serene backdrop against the clear blue sky.
Guest suite in Dover Plains
4.91 out of 5 average rating, 331 reviews

Hoppy Hill Farm House

Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Plenty of quaint towns near-by: Kent, Millbrook, Amenia, Wassaic for great food, coffee shops, antiques, parks, breweries and vineries. Inside, you will feel right at home in this comfortable one bedroom apartment.

Top guest favourite
The exterior of a cottage is shown, featuring a dark blue façade with a shingled roof and a central star accent. A welcoming porch is lined with four red chairs and decorative flower pots. Lush green grass and trees provide a serene setting.
Cottage in Clinton Corners
4.95 out of 5 average rating, 232 reviews

(Hudson Valley) Laughing Duck Cottage

Located in the bucolic Hudson Valley, this new, gut-renovated cottage isn't far from many of the area's most loved spots. In the winter you can wander trails and get cozy by our electric fireplace. In the spring you can picnic your way through historic sites and enjoy a glass of local wine on our back deck. In the summer you can ride a horse and cook with seasonal ingredients from local farms. In the fall you can hike through the Hudson Valley's perfect colors and sip hot cider on our back deck.

Top guest favourite
A well-maintained exterior view showcases a single-story house with a gray siding. A small patio area features a wooden picnic table surrounded by flower beds and a stone pathway. Lush greenery frames the space, while a clear blue sky fills the backdrop.
Flat in Verbank
4.96 out of 5 average rating, 159 reviews

Large, private apartment in scenic Hudson Valley

We are located right in the middle of the Dutchess County so access to all points is convenient. Many attractions are: historical Hyde Park, Walkway Over The Hudson, Culinary Institute, Vassar & Marist colleges, wineries, breweries, the quaint towns of Millbrook & Rhinebeck, Dutchess County Fairgrounds, and The Links At Unionvale golf course and banquet hall. Great for couples, adventurers and business travelers who love activity but appreciate a comfortable quiet place at the end of the day.

Guest favourite
A serene river scene showcases vibrant autumn foliage reflected in calm water. Brightly colored trees in shades of orange and yellow surround a white house nestled among them, set against a backdrop of blue sky and scattered clouds.
Home in Millbrook
4.9 out of 5 average rating, 150 reviews

Serene Waterfront Mill House, Stroll to Village

Sweet 1840 mill house on the water, nature-filled back deck yet 5 mins walk to antiquing & excellent Millbrook restaurants. Make this your base as you explore the beautiful Hudson Valley. Or relax out back & enjoy the birds & stream. Farmhouse antique shabby chic decor with king tempurepedic bed in large second floor master BR, two BRs with twin trundle beds, 1 bathroom upstairs & 1 down, A/C, ceiling fan, cozy woodstove, wifi with smart tv, eat-in kitchen, coffee/tea, plenty of free parking.

Superhost
A charming cottage is depicted, featuring a dark exterior with bright pink doors. Two pink chairs and a small table are positioned outside on a gravel area, surrounded by potted plants. Trees frame the backdrop, contributing to a serene setting.
Guest house in Dover Plains
4.87 out of 5 average rating, 126 reviews

Spilt Milk Cottage - Hudson Valley, NY

Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

Top guest favourite
The kitchen features modern white cabinetry with black handles, complemented by a light-colored countertop. A stainless steel sink is positioned under a wall-mounted faucet. A tile backsplash in neutral tones adds texture, while a fire extinguisher is mounted for safety.
Flat in Pine Plains
4.98 out of 5 average rating, 218 reviews

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.

Top guest favourite
A bright living room features a sofa facing large glass doors that open to a view of the forest. A cozy armchair is situated nearby, along with a simple coffee table. A bookshelf contains various items, and a wood stove is positioned in the corner.
Guest house in Stanfordville
4.93 out of 5 average rating, 186 reviews

Eco Cottage in the Woods

The cottage is light and airy, surrounded by forest. You may see birds and deer from the bedroom or living room. The queen bed is divided from the living room by a bookcase wall. There is a sofa bed in the living room which faces a patio overlooking the woods. We have a 16x36 unheated gunite pool, professionally maintained. The cottage works well for a couple or a couple with children. 2 night minimum required. Pets welcome. Pet owners passing through may stay 1 night.

Guest favourite
The exterior of a charming cottage is seen, featuring a front porch with two black chairs and potted plants. Stone steps lead up to the entrance, flanked by shrubs and trees, creating a serene setting within the landscaped grounds.
Cottage in Rhinebeck
4.93 out of 5 average rating, 174 reviews

Intimate Cottage on Private Estate

Bulls Head Cottage is a thoughtfully-designed retreat nestled within a 2.5 acre estate 5 minutes from Omega Institute and 10 minutes from the charming Village of Rhinebeck. The 720 square foot guest cottage is a relaxing place for up to 2 guests, offering cozy indoor and outdoor space including an office overlooking the property's pond. Enjoy quick access to hiking, shopping, fine dining and more. Under 2 hours from New York City by car or train. Pets not typically allowed.

Superhost
A gentle waterfall cascades over rocky terrain, surrounded by autumn foliage in varying shades. The water flows into a clear pool, with smooth stones lining the edges. Tall trees in the background create a lush, green canopy, while fallen leaves blanket the ground.
Cabin in Rhinebeck
4.88 out of 5 average rating, 398 reviews

Sunset Bungalow-Mt views on 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, and comfortable bedroom- learn more at cascadafarm.com

Guest favourite
An airy room is highlighted by wooden beams and large windows that overlook greenery. A spacious bed with a patterned duvet is positioned beside a cozy bed. A round table and chairs are situated in one corner, complemented by a woven rug and a decorative basket.
Home in Rhinebeck
4.96 out of 5 average rating, 194 reviews

Honeybug Snug near Omega Institute!

Welcome to the Honeybug Snug! Now with AIR CONDITIONING : ) The Snug is perfect for a family of 4 or 4 close friends. : ) We still have a little work to do on her and you get to watch her grow. Your comments will be taken to heart, as your comfort is our priority! We live right next door if you need anything : ) We are .9 miles for The World Renowned Omega Institute -Center for Holistic Studies. Less than 15 Minutes to Downtown Rhinebeck.

Guest favourite
A warmly colored wooden front door features a large window at the top and is adorned with a seasonal wreath. Two carved bear statues stand on either side, complementing a welcome mat placed at the entrance.
Flat in Millbrook
4.93 out of 5 average rating, 235 reviews

Red Tail Ridge

One BR with bath, full kitchen, eating area and living room. Separate entrance and sliding glass door in rear with country views. Located on 12 acre parcel. Close to village of Millbrook (less than 4 miles). We are located in center of Dutchess County. There is great antique shopping, historic sites and some of the finest restaurants and chefs with tastes to suit most everyone. .

Popular amenities for Millbrook holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Dutchess County
  5. Millbrook