Holiday rentals with outdoor seating in Poughkeepsie

Guest suite in Wappingers Falls

4.83 out of 5 average rating, 131 reviews

Private ground floor guest suite in Hudson Valley

Guest favorite/newly renovated/private, ground floor guest suite. Br/full bath/large LR w/big TV/frig/mw/coffee in centrally located area in the heart of Hudson Valley. Walk to Dutchess Rail Trail/Uber accessible/self ck in. Close to Poughkeepsie, Beacon, Vassar/Marist/DCC colleges, Walkway over Hudson, Culinary Institute, Vassar Hospital, Hyde Park, New Paltz, Rhinebeck. Couch only in LR would be ok for a child. Pets considered for $15/night fee w/inquiry prior. No full kitchen. Car suggested.

ValueLocationCheck-in

4.99 out of 5 average rating, 179 reviews

The inviting interior features a well-lit living space with decorative wall sconces and a cozy seating area. A wooden table stands near a lush fern, while a TV is positioned on a mantel beneath framed artwork. Natural light enhances the space's warmth.

Apartment in Marlboro

Cozy Hudson Valley Retreat | 1800s Farmhouse

Come relax at our lovingly restored historic 1873 Marlboro Farmhouse centrally located between Beacon, New Paltz, Kingston, and West Point; and close to many local farms, orchards, wineries, and fantastic hiking trails. The farmhouse is split into three separate and private units. This listing is for the spacious 1400sq. ft 2 BR/2.5 bath unit that occupies the private second floor. This is NOT a party house. The only guests allowed on the property are the ones listed on the reservation.

ValueOutdoor spacesQuiet

4.99 out of 5 average rating, 129 reviews

A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.

Home in Staatsburg

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Outdoor spacesLocationAccess

4.94 out of 5 average rating, 284 reviews

Home in Wappingers Falls

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. I look forward to hosting you. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door. We have added a separate kitchenette additional crockpot and induction cooktop.

LocationOutdoor spacesQuiet

Superhost

The outdoor patio features a gravel pathway leading to a centrally located fire pit, surrounded by four comfortable chairs. A pink umbrella shades a nearby table with four chairs, and lush greenery enhances the tranquil ambiance of the enclosed backyard.

Apartment in Poughkeepsie

4.89 out of 5 average rating, 114 reviews

Under the walkway near the train in Little Italy

Beautiful downtown apartment under the walkway over the Hudson. It sits on one of the nicest streets in a safe neighborhood within walking distance to the metro north train station (3 blocks), restaurants (across street from Farmers and Chefs), bars and bakeries. The walkway is also near by. Outdoor back patio and fire pit are exclusive for this listing. There is also a studio below that can be rented which will give you the entire building. Be mindful of the guests staying down stairs.a

Outdoor spacesValueKitchen

4.98 out of 5 average rating, 179 reviews

A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.

Home in Kingston

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

Outdoor spacesLocationBackyard

Apartment in Poughkeepsie

4.9 out of 5 average rating, 105 reviews

The Hudsy Home

Welcome to our cozy retreat nestled in the heart of the Hudson Valley! Your escape awaits with a personal entrance to this cozy apartment inside our home. Unwind in the spacious bedroom, perfect for a couple's night's sleep. The living area features a 65-inch flat-screen TV for your enjoyment. Walkway Over The hudson is just a short 5-minute stroll away. For your convenience, you're only moments away from local favorites like Starbucks, Chipotle, CVS, Shoprite and more :)

LocationValueCleanliness

Guest suite in Poughkeepsie

A landscaped backyard is visible, featuring a stone pathway leading to a seating area with a patio table and an umbrella. Vibrant flowers and greenery surround the space, creating a tranquil outdoor environment with diverse foliage and decorative elements.

4.96 out of 5 average rating, 150 reviews

Suite of Rooms in Historic Home

Wonderfully decorated 3rd floor suite of rooms in the Academy Historic District. Two Newly renovated bedrooms, one with queen bed, the other with 2 twin beds. There is an additional day bed in the living area/ sitting room space , a TV with Netflix & Amazon Prime with wifi connection throughout. The bathroom has modern fixtures and a claw-foot tub/shower. There is a private entrance with additional half bath . A private porch and use of the beautiful backyard.

ValueLocationView

4.95 out of 5 average rating, 379 reviews

A light-filled living room features a comfortable seating arrangement with beige and blue accents. A decorative fireplace is positioned below a mounted TV, showcasing a scenic view. Large windows allow natural light to brighten the space, complemented by a patterned rug and a round coffee table.

Home in Poughkeepsie

4BR|2Bath|King Beds|Walk to Marist|CIA|Pet|Parking

This home is located in the Mid Hudson Valley -just steps away from Marist U, The entrance to Walkway Over the Hudson, MHR Hospital and a 2mi ride to the CIA! Equipped with a full kitchen, king beds, 2 full baths, Roku TV, private parking & spacious backyard- perfect for grilling or cozying up next to the fire pit. Make this cheerful house your home base as you explore all the wonders of the Hudson Valley! We are a small dog friendly! (15 lbs or less)

Outdoor spacesLocationQuiet

4.97 out of 5 average rating, 102 reviews

Aerial view captures a modern white home set against a backdrop of vibrant fall foliage. The expansive Hudson River glistens below, framed by lush trees and rolling landscapes, emphasizing the tranquility and natural beauty of the surroundings.

Guest suite in Highland

Modern/lux suite on Hudson Riverfront w/views!

Come stay on the Hudson River Waterfront Bluff! It is one of THE most magical, luxurious experiences in all of NY. The views are insane!! It's literally the perfect getaway with a major *wow* factor - if you're wanting something very special. :) You'll have complete access to my gorgeous, modern, designer 2-room guest suite. The entrance is separate/private. This is a luxury escape. The central location positions you near everything!

ValueOutdoor spacesView

4.86 out of 5 average rating, 100 reviews

An entertainment area is displayed with a wall-mounted television above a sleek console. A decorative lamp and a wooden sculpture add warmth. A serving tray with glasses and an ice bucket is positioned nearby, along with a board game for casual gatherings.

Home in Highland

Hudson Valley Boutique Airb&b

Bring the whole family to this great place with lots of room for fun. Located in The Hudson Valley in close proximity to" Walkway over The Hudson" , New Paltz, Lake Minnewaska, Beacon, Poughkeepsie, New Paltz, and Woodstock ! Grill out on the back deck or visit one the wonderful local restaurants! Within 10 minute ride to Marist College, Vassar College, The Culinary Institute of America, And SUNY New Platz College.

Outdoor spacesValueKitchen

4.99 out of 5 average rating, 788 reviews

A light-filled sitting area features large windows showcasing views of the river and surrounding hills. Two black armchairs and a round table with two chairs are positioned on a polished wooden floor, creating a serene space for relaxation.

Guesthouse in Hyde Park

Modern cottage with Hudson River view

Relax and enjoy your stay in a bright, modern cottage with windows overlooking the river and a wraparound deck. Whether you are looking to relax along the river, explore Hyde Park historic properties or discover the incredible natural beauty of the Hudson Valley, this cottage is an ideal escape.

Outdoor spacesLocationHospitality

Popular amenities for Poughkeepsie outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.96 out of 5 average rating, 174 reviews

An open living space features a Foster Leather sectional sofa positioned around a central coffee table. Natural light streams in from a large window, illuminating the wood-burning stove nearby. A cozy area rug adds texture to the floor, creating an inviting atmosphere.

Home in Gardiner

Mindful Escape: Theater, Trails, Wood Stove

ValueOutdoor spacesBathroom

4.98 out of 5 average rating, 128 reviews

A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.

Home in Rhinebeck

Slate Cabin - Stylish Country Escape x Rhinebeck

Outdoor spacesLocationQuiet

4.76 out of 5 average rating, 191 reviews

A spacious living area features a light-colored couch alongside a round coffee table. Sliding doors provide separation from the sleeping area, which contains a large bed dressed in light linens. Natural light filters through the nearby windows, illuminating the warm wooden floor.

Home in Milton

Historic 1 BR Family Home Near Buttermilk Falls

ValueLocationShared spaces

4.94 out of 5 average rating, 388 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

ValueOutdoor spacesBathroom

4.97 out of 5 average rating, 304 reviews

A charming two-story house features warm wooden siding and multiple red window accents. A welcoming front porch is adorned with lights, complemented by a gently sloped pathway leading up to the entrance, surrounded by lush greenery and seasonal foliage.

Home in New Paltz

Eclectic one-bedroom house

LocationOutdoor spacesView

4.94 out of 5 average rating, 124 reviews

A comfortable living room is shown, featuring a dark leather sofa adorned with colorful pillows. A light-colored coffee table sits atop a patterned area rug. Natural light enters through nearby windows, and an armchair with floral upholstery is positioned beside a lamp.

Home in Staatsburg

3 Bedrooms close to Rhinebeck NY

LocationValueAccess

4.96 out of 5 average rating, 153 reviews

A spacious living area showcases light-colored sofas arranged around a wooden coffee table. Large windows provide views of the lush outdoors, while a patterned rug anchors the space. A chair and stylish lamps enhance the inviting atmosphere.

Home in Staatsburg

Nature Retreat with Pond Views and Fire Pit

ValueLocationDecor

4.94 out of 5 average rating, 127 reviews

A spacious living room is presented, featuring a comfortable green sectional sofa with decorative pillows. A wooden coffee table with magazines rests in front, and a mirror is mounted above a side table adorned with a lamp. A cozy armchair is positioned nearby.

Home in Hyde Park

Hyde Parks Hideaway

ValueOutdoor spacesLaundry

Apartment rentals with outdoor seating

4.91 out of 5 average rating, 118 reviews

Apartment in Hyde Park

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

ValueOutdoor spacesKitchen

4.78 out of 5 average rating, 692 reviews

The exterior of a historic stone farmhouse is shown, featuring a vine-covered wall and landscaped garden. Steps lead to the entrance, surrounded by greenery and floral elements, with large windows allowing natural light. The serene outdoor setting reflects the charm of the surrounding countryside.

Apartment in High Falls

Art Room at Old Stone Farmhouse

LocationValueCheckout

4.91 out of 5 average rating, 141 reviews

A cozy dining area features a small table set with a green tablecloth, flanked by two wooden chairs. A comfortable bench sits against the wall, with a floor lamp providing soft lighting. Natural light enters through a window adorned with light curtains, highlighting the green walls.

Apartment in New Paltz

Enthusiastic Spirits. Close to Parks W/Cliff Views

Outdoor spacesLocationCleanliness

5 out of 5 average rating, 121 reviews

Apartment in Holmes

Top Side

ValueOutdoor spacesBathroom

4.96 out of 5 average rating, 215 reviews

A welcoming studio space is furnished with a pink sofa, a wooden coffee table, and a dining area with a table and chairs. Light enters through a sliding glass door, revealing views of the wooded backyard. A small television is positioned near the seating area.

Apartment in Tillson

Woodland Neighborhood Retreat

Outdoor spacesLocationHiking

5 out of 5 average rating, 141 reviews

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.

Apartment in Pawling

Quiet Studio Apartment in Pawling

Outdoor spacesLocationDecor

4.91 out of 5 average rating, 178 reviews

A serene pond is situated within a wooded landscape, featuring a fountain that sends water into the air. Surrounding greenery includes trees and bushes, with a flag pole visible nearby. The lawn is well-maintained and enhances the peaceful ambiance of the property.

Apartment in Hyde Park

The House By The Pond

ValueOutdoor spacesAccuracy

4.89 out of 5 average rating, 260 reviews

Apartment in Newburgh

Special Nest w Private Entrance River View Porches

ValueOutdoor spacesComfort

Condo rentals with outdoor seating

Superhost

A spacious outdoor deck is visible, furnished with a round table surrounded by several chairs and a lantern on top. A comfortable seating area with a couch is positioned nearby, set against a backdrop of lush greenery.

Condo in Windham

4.67 out of 5 average rating, 123 reviews

Windham Condo

Outdoor spacesValueHospitality

A spacious living area includes a cozy sitting area with large windows offering views of the surrounding landscape. A decorative fireplace adds warmth, while a small desk and chair provide a functional workspace. A dining table complements the layout, enhancing the room's versatility.

4.92 out of 5 average rating, 291 reviews

206 · Renovated Chic Premium 1 bdrm

Outdoor spacesLocationComfort

4.97 out of 5 average rating, 703 reviews

A modern living area features a dark blue sofa and a coffee table with decorative items. The open kitchen showcases stainless steel appliances and a dining area with four bar stools. Warm lighting enhances the inviting space, while wall art adds character.

Condo in Lanesville

Ski on/ Ski off Country Condo Hunter Mountain

Outdoor spacesValueParks

4.98 out of 5 average rating, 107 reviews

Cozy Luxury Mountain Retreat 2BR/2BA | Water Park

ValueOutdoor spacesTV

The living area features high ceilings and a spiral staircase leading to the loft. A blue couch faces a Smart TV, accompanied by a coffee table. A round dining table with blue placemats and four chairs is positioned nearby, offering an open view of the kitchen.

4.92 out of 5 average rating, 394 reviews

BRAND NEW! MODERN SlopeSide Condo, Golf, & Spa

LocationOutdoor spacesBiking

A spacious living area is highlighted by a sectional sofa, positioned near large windows that welcome natural light. A dining table set for six is visible, complemented by a stylish chandelier above. A staircase with wooden steps adds a unique architectural element to the space.

4.99 out of 5 average rating, 145 reviews

Skiiis N Tees • Mountain Views, Cozy Vibes

ValueLocationWalkability

A spacious living area is shown, featuring a contemporary design with a large gray sofa and a plush purple chair. An elegant dining table sits beside the window, while a flat-screen television is mounted on the wall, complemented by a stylish mirrored console below.

4.94 out of 5 average rating, 136 reviews

The Oasis of Vernon

ValueLocationQuiet

A serene bedroom space features a spacious bed adorned with cozy linens and decorative throw pillows. Geometric wall carvings in dark tones create an artistic backdrop, complemented by bedside lamps providing soft lighting. Natural light fills the room through a nearby window.