Apartment holiday rentals in Dutchess County

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Dutchess County

Guests agree: these apartments are highly rated for location, cleanliness and more.

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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

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.

FamilyValueHeating

4.91 out of 5 average rating, 180 reviews

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

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.

ValueLocationView

4.97 out of 5 average rating, 184 reviews

Top guest favourite

A spacious studio apartment features large windows allowing natural light to fill the room. A comfortable king size bed is positioned alongside a cozy seating area with a sofa and coffee table. A textured area rug covers the hardwood floor, adding warmth to the space.

Flat in Pawling

Quiet Studio Apartment in Pawling

For getaways or visiting the area, this peaceful sanctuary awaits your arrival in Pawling. A fresh clean studio apartment with idyllic views of the forest, stone walls, and distant mountains. Awake to the sound of birds and beautiful sites. With a king size bed, kitchenette, desk, Smart TV, WIFI, full bath with walk-in shower. Big sliding glass door to private deck overlooking native landscaping. 1 mile to village for restaurants, bakeries, & night spots. 7 min by taxi to Darryl's House Club.

LocationFamilyCondition

5.0 out of 5 average rating, 155 reviews

Top guest favourite

Flat in Holmes

Top Side

Welcome to Top Side! Nestled in Holmes, NY, Top Side offers lovely views of Whaley Lake. Whether you're looking for a relaxing getaway or an adventure, you'll find plenty of reasons to fall in love with this spacious apartment which is designed to help you unwind and recharge. The Hudson Valley is brimming with activities and attractions for everyone. From historic landmarks and charming villages to outdoor adventures and local dining, you're never far from something special to experience.

FamilyLocationOutdoor spaces

5.0 out of 5 average rating, 150 reviews

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

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.

ValueFamilyWalkability

4.96 out of 5 average rating, 289 reviews

Top guest favourite

A spacious bedroom features a wrought iron bed dressed in neutral linens, accompanied by decorative pillows. Exposed brick and stone walls add character, while wooden beams and a warm area rug enhance the inviting atmosphere. Soft lighting from bedside lamps casts a gentle glow.

Flat in Kingston

Garden apt with river views in downtown Kingston

Lovingly restored garden level apt in 1870's Victorian. Sweeping Hudson River views (with private patio) and just steps away from the entrance for the Kingston Point Rail Trail. Quick 1/2 mile walk to restaurants, shops and boats in Kingston's downtown historic West Strand. One mile walk to events at Hutton Brickyards. California king bed, Central A/C, washer-dryer. and full kitchen in unit! Designed by dog lovers (dogs 45 lbs and under are typically most comfortable due to size of space).

LocationFamilyBack garden

5.0 out of 5 average rating, 130 reviews

Guest favourite

The entrance features a striking red door adorned with a brass plaque labeled 'DeMew Townhouse.' Lush green vines and colorful flower pots with blooming flowers are positioned at the foot of the stairs, enhancing the welcoming atmosphere of the entryway.

Flat in Kingston

DeMew Townhouse in Historic Kingston

DeMew Townhouse is beautiful duplex apartment located in a renovated 1850s building overlooking Hideaway Marina in the Rondout district of Kingston. The building boats a rich history: the main floor of the building served as a speakeasy during Prohibition. It has hand rubbed oak floors, a renovated kitchen and bath and 14 windows providing views of the Rondout. With a spacious open plan, the DeMew Townhouse is the perfect location from which to explore Kingston and the Hudson Valley.

FamilyValueKitchen

4.95 out of 5 average rating, 321 reviews

Guest favourite

Flat in Hyde Park

Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1

Step into the serene rural charm of the Hudson Valley for a unique retreat at our llama and alpaca farm. Nestled along charming country roads, our farm offers an escape from city life and the noise of modern living. Stay in a cozy apartment overlooking a peaceful pasture, where the absence of noise pollution lets you fully embrace the sounds of nature. Whether seeking to reconnect with the outdoors or savor the tranquility, our farm promises an unforgettable countryside experience.

FamilyValueBathroom

4.88 out of 5 average rating, 139 reviews

Guest favourite

The exterior of the house is framed by lush greenery, featuring a covered porch and a picnic table shaded by a red umbrella. A chiminea is positioned nearby, creating an inviting outdoor space. The gray siding complements the natural surroundings.

Flat in Dover Plains

*The Ridge House*

Escape to a quiet, pleasant and serene getaway at The Ridge House. A lovely attached apartment with private entrance and covered deck to enjoy the sights and sounds of nature. Stop by the stream down the hill with a drink or enjoy the sunrise while reading outside. Roast marshmallows in the fire after dinner on the grill and finish the day relaxing in the comfortable queen bed. (Airbnb now hides their fees in the listing price, the host cannot change them).

LocationFamilyGrill

4.95 out of 5 average rating, 177 reviews

Guest favourite

The exterior of a rustic cottage is presented, featuring large windows that allow natural light to fill the interior. A wooden deck leads to a glass-paned door, framed by light-colored siding and contrasting trim. Trees and greenery are visible in the background.

Flat in Salt Point

Arcady - Modern, 1br cottage

Renovated 600 sq ft 1br/1ba cottage! Welcome to Arcady - an ideal rustic paradise. Our recently renovated barn cottage situated on 6 acres of land with private creek and within easy drive of Rhinebeck, Millbrook, Omega Institute, Poughkeepsie and thousands of Hudson Valley Attractions. 10 min drive from Omega, 1 min drive from a town beach - enjoy everything area has to offer including hikes, mansions, farm visits, wineries and much more.

FamilyLocationGrill

4.85 out of 5 average rating, 213 reviews

Top 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

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. .

FamilyLocationCondition

4.94 out of 5 average rating, 248 reviews

Guest favourite

The exterior of the cabin is illuminated by soft lighting, highlighting the double doors and windows. The building features a sloped roof and is surrounded by lush greenery, creating a serene environment in the evening. A simple bench is positioned on the grassy area in front.

Flat in Millbrook

The Bennett Cabin

Serene setting....private cabin, part of a duplex with bedroom and bathroom on second floor and living area and kitchen on first floor. Situated on creek, part of 5 acre estate, walk to Orvis Sandanona, right next door, 2 miles to Millbrook Village, 3 miles to Millbrook Vineyards, and close to many Hudson Valley historic sites. Fall asleep to the flowing stream.

FamilyLocationPets

4.86 out of 5 average rating, 121 reviews