Poughkeepsie vacation rentals

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Top-rated vacation rentals in Poughkeepsie

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Guest favorite

Farm stay in New Paltz

4.92 out of 5 average rating, 612 reviews

The 1772 Lefevre Stonehouse Suite

Sit at a quaint breakfast table in this sun-filled room admiring the beautiful patio, grainy wood-plank floors, and a country decor touches. Walk outside to enjoy the rustic grounds of this enchanting stone-built home dating from 1772. The suite has its our private entrance, bathroom and fireplace all stocked with plenty of firewood for your stay. Fireplace can be used November-March only unless temperatures are under 40 degrees. Our home is located just seven minutes from New Paltz and two minute from Gardiner. The property is on 60 acres of rural land that you are welcome to explore. The room includes a queen size bed, a pullout futon for an extra (small) person, mini fridge, microwave and coffee machine. Enjoy your morning coffee on the large stone patio while listening to the roosters crow and birds singing. We raise around 250 egg layer chickens and 800 meat chickens on the property. They Love treats from you. If you’d like they will take snacks right from your hand. The roosters are tame and friendly. We now also have Lucy the goose. She watches over the chicken flock. The rail trail, where you can bring your bike and ride into New Paltz, is only a quarter of a mile away through our property then down a quiet country road. Our home is just minutes from Minnewaska State Park, Mohonk Preserve, and the historic Mohonk Mountain House. The New Paltz area has some of the finest restaurants you can dine at. The Town of Gardiner is only two minutes down the road. There you will find Café Mio and a pizzeria for a quieter dining experience. Gardiner also has Yard Owl Brewery, Gardiner Brewing Company (this is my son and daughters newly opened farm brewery on our main farm property in our old dairy barn), The Gardiner Mercantile and Tuthilltown Spirits each of which are great places to stop in and have a drink and a lite meal. Wright's Farm (Our Farm) is also 1 mile south on 208 features homemade baked goods, local cheeses, fruits and vegetables, fresh from the farm pork and chicken, wine, local spirits, hard cider Gardiner Brewing Company canned beer, bedding plants and fabulous hanging baskets and finally pick your own strawberries (second week in June-end of June), cherries (third week in June-first of July) and apples in September and October. The guest have their own access via private entrance to the bedroom suite , hot tub and the 60 acres. We are farmers and work a lot therefore we are only here early in the morning and after 7 or 8 o'clock at night. At those times we would love to interact with our guest if they are willing. If guest would like to come to our farm we are always here to talk to our guests and if we have time give them a tour of our farm and new farm brewery. Set on secluded grounds, this Historic stone home is situated on 60 acres of land with chickens, ducks and 3 goose as our neighbors. The Hamlet of Gardiner is a 3-minute drive away, and New Paltz is just a bit farther. It’s best if you have a car. There is no public transportation here. You can get a taxi or an Uber from New Paltz. Bring your bikes. The rail trail is only 1/4 mile away. Drive your car into the town of Gardiner and park at the rail trail parking lot. If you are coming by bus you will arrive in New Paltz. From there you will need to take a taxi or Uber to our home. This is a very rural area so please stop at the store prior to your arrival. We do have a supermarket that is 3 miles away and Wright's Farm Market open 8-6 year round that is 1 mile away. If you bring your dog please be a where that you may not leave the dog in the room unattended.

Sep 1 – 8

R2,701 ZAR per night

Superhost

Apartment in Wappingers Falls

4.84 out of 5 average rating, 217 reviews

Private Spacious Strawberry Hill Loft Home

Private spacious and sparkling clean loft apartment just minutes from Metro North station, Rt 9, active Wappinger Falls, Beacon, DIA and Poughkeepsie downtown waterfront. Walkway Over the Hudson, Marist College, Vassar College, Locust Grove, Roosevelt Mansion, Mount Beacon, Catskills, New Paltz, Bowdoin Park minutes away. 15 ft cathedral ceilings and windows are sure not to disappoint! Located on a quiet private street perched atop a buff with views of beautiful sunsets over the Hudson Valley.

Jun 8 – 15

R2,626 ZAR per night

Guest favorite

Condo in Poughkeepsie

4.97 out of 5 average rating, 223 reviews

Spacious and stylish entire one bedroom apartment.

Enjoy a stylish experience at this centrally-located one bedroom apartment in Poughkeepsie. Apt is located in a quiet Victorian townhouse on the 3rd floor. Entire rental unit, Parking is included for one vehicle. Located downtown. Walking distance to: Post Office, Courts, County Bldgs, Police Station, City Hall, Nesheiwat Convention Center (fka Civic Center), Poughkeepsie Grand Hotel, Walkway Over The Hudson, Bardavon Opera House, The Academy, train station, waterfront, bus depot, and more.

Jun 26 – Jul 3

R2,685 ZAR per night

Guest favorite

Cottage in Highland

4.91 out of 5 average rating, 537 reviews

Little Yellow Cottage New Paltz - Kitchen wash/dry

Built over 100 years ago as a chicken hatchery, this gorgeous little gem has been fully restored as a two-story guest cottage. Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only ten minutes from New Paltz Village & SUNY New Paltz and set back on a lightly traveled road for those long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station or bring your bike up and cycle everywhere!

Jun 12 – 19

R3,380 ZAR per night

Guest favorite

Home in Kingston

4.97 out of 5 average rating, 274 reviews

This New House

Unique custom built new home constructed purposefully for Airbnb quests. This house offers a distinctive design with a large loft bedroom and a fully tiled bathroom. The loft overlooks the downstairs living area which has an open living room, dinning area, and kitchen. The second bedroom and bath are located on the first floor. Granite, slate, and soapstone accentuate the countertops, vanities, and floors. You will also see plenty of natural pine, hickory, and local cedar throughout the house.

Dec 9 – 16

R2,769 ZAR per night

Guest favorite

Apartment in New Paltz

4.96 out of 5 average rating, 344 reviews

Modena Mad House

Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in

Jan 12 – 19

R2,192 ZAR per night

Guest favorite

Home in Hyde Park

4.86 out of 5 average rating, 181 reviews

Village Cape Getaway

Village Cape on Albany Post Rd in the historic town of Hyde Park. Surrounded by gardens, stone walls, private parking/entry. This 2 story house offers a 1 bdrm apartment that sleeps 3 on the 2nd floor. Close to markets, shops, restaurants. 1 mi to Vanderbilt Mansion, FDR house and library. 2mi to the Culinary Institute of America. 4mi to Marist College. Hiking trails walking distance. Historic drive-in movie in town. Metro north Poughkeepsie sta 6mi south offering taxi and bus service.

Dec 16 – 23

R1,952 ZAR per night

Guest favorite

Guest suite in Marlboro

4.96 out of 5 average rating, 391 reviews

Spacious & Private Hudson Valley Getaway

Welcome to Marlboro! This private space in our home features a private entrance, private bathroom with a nice standing shower, eating area (not a kitchen) with tea kettle and coffee machine, toaster, microwave and refrigerator with freezer. There is a table and chairs, love seat couch that transforms into a small cot, queen bed, walk in closet and 55 inch smart TV with a full motion TV stand. We are permitted to operate in the town of Marlboro and a yearly fire inspection is conducted.

May 10 – 17

R2,119 ZAR per night

Guest favorite

Apartment in Poughkeepsie

4.95 out of 5 average rating, 285 reviews

3 Bdrm. Near Hudson Valley Colleges & Attractions

Built in 1910, this 3 bedroom apartment is located close to many Hudson Valley attractions - only 0.5 miles from the Poughkeepsie train station. Located within 2 miles of both Marist and Vassar Colleges, as well as a short drive from The Culinary Institute of America. Historic villages of Hyde Park and Rhinebeck are just a short drive along the river. As well as fast access to hiking and biking trails in local Shawangunk mountains, Mohonk Preserve, and Minnewaska State Park.

Aug 29 – Sep 5

R3,017 ZAR per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 741 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Jul 4 – 11

R2,107 ZAR per night

Guest favorite

Home in Highland

4.96 out of 5 average rating, 141 reviews

The Grove: beautiful two bedroom home

The Grove is a cozy two bedroom house located steps away from the village of Highland. We are also a quick drive to not only the best hiking trails but also apple orchards and wineries. The house is equipped with a fully renovated kitchen, washer/ dryer, fenced in back yard, and two parking space driveway. With original craftsman style trim throughout the house you will love staying in our home. All pets are welcome… please review House Rules section for pet fee.

Oct 3 – 10

R3,185 ZAR per night

Guest favorite

Home in Wappingers Falls

4.98 out of 5 average rating, 102 reviews

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. Be our guest at our beautiful home located on the widest part of the Hudson River. 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.

Aug 12 – 17

R3,084 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Poughkeepsie vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Poughkeepsie's top sights

Locust Grove Estate49 locals recommend

Vassar Brothers Medical Center8 locals recommend

Vassar College58 locals recommend

Palace Diner4 locals recommend

Shadows on the Hudson49 locals recommend

Mill House Brewing Company76 locals recommend

Other great vacation rentals in Poughkeepsie

Guest favorite

Home in Hyde Park

4.9 out of 5 average rating, 470 reviews

Cozy ranch near FDR Historical Site

Oct 4 – 11

R3,636 ZAR per night

Guest favorite

Home in Highland

4.96 out of 5 average rating, 107 reviews

House in Highland: Secluded Retreat

Jan 14 – 21

R6,011 ZAR per night

Guest favorite

Home in Poughkeepsie

4.97 out of 5 average rating, 158 reviews

Oct 5 – 12

R3,951 ZAR per night

Guest favorite

Cabin in Highland

4.92 out of 5 average rating, 458 reviews

Country Log Home Retreat

Aug 19 – 26

R3,766 ZAR per night

Guest favorite

Apartment in Staatsburg

5.0 out of 5 average rating, 187 reviews

Through the Woods Farm

Oct 28 – Nov 4

R2,812 ZAR per night

Guest favorite

Tiny home in Newburgh

4.88 out of 5 average rating, 521 reviews

Cabin in the heart of the Hudson Valley, Cabin 2

Dec 16 – 23

R2,454 ZAR per night

Guest favorite

Apartment in Rhinebeck

4.95 out of 5 average rating, 441 reviews

Cozy private apartment in Rhinebeck Village

Dec 22 – 29

R1,987 ZAR per night

Guest favorite

Cottage in Clintondale

4.93 out of 5 average rating, 166 reviews

The cottage at Maple Ave - upstate mountain view

Dec 6 – 13

R2,546 ZAR per night

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Other great vacation rentals in Poughkeepsie

Guest favorite

Loft in New Paltz

4.94 out of 5 average rating, 202 reviews

Cozy Couples Retreat w/ Short Walk Into New Paltz

Mar 30 – Apr 6

R2,446 ZAR per night

Guest favorite

Apartment in Millbrook

4.93 out of 5 average rating, 205 reviews

Red Tail Ridge

Aug 7 – 14

R2,474 ZAR per night

Guest favorite

Apartment in Hyde Park

4.92 out of 5 average rating, 161 reviews

The House By The Pond

Jun 17 – 24

R2,961 ZAR per night

Guest favorite

Home in Poughkeepsie

5.0 out of 5 average rating, 9 reviews

Newly Renovated Studio - In Heart of Poughkeepsie

Aug 7 – 14

R2,433 ZAR per night

Guest favorite

Apartment in Poughkeepsie

4.94 out of 5 average rating, 16 reviews

The Hudsy Home

Nov 7 – 14

R2,080 ZAR per night

Guest favorite

Apartment in Arlington

4.91 out of 5 average rating, 47 reviews

Arlingtons Finest

Feb 26 – Mar 5

R2,289 ZAR per night

Guest favorite

Apartment in Poughkeepsie

4.92 out of 5 average rating, 72 reviews

Studio under the Walkway over the Hudson

Aug 6 – 13

R2,003 ZAR per night

Superhost

Yurt in Poughkeepsie

5.0 out of 5 average rating, 8 reviews

Fun YURT Glamping

Dec 6 – 13

R1,139 ZAR per night

Show all

Quick stats about vacation rentals in Poughkeepsie

Total rentals
100 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
5.2K reviews
Nightly prices starting at
R767 ZAR before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Poughkeepsie?
Yes! Work meets play with ease at over 50 vacation rentals in Poughkeepsie featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Poughkeepsie?
Four-legged friends are welcome in Poughkeepsie. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Poughkeepsie?
Experience the best of Poughkeepsie with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Poughkeepsie have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Poughkeepsie. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Poughkeepsie have wifi?
Absolutely! We offer over 40 apartment rentals with wifi in Poughkeepsie. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Poughkeepsie have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Poughkeepsie. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Poughkeepsie?
Poughkeepsie has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Poughkeepsie?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wifi, over 30 homes with air conditioning, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Poughkeepsie vacation rentals

Top-rated vacation rentals in Poughkeepsie

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Poughkeepsie vacation rentals

Stay near Poughkeepsie's top sights

Other great vacation rentals in Poughkeepsie

Home in Hyde Park

Home in Highland

Home in Poughkeepsie

Cabin in Highland

Apartment in Staatsburg

Tiny home in Newburgh

Apartment in Rhinebeck

Cottage in Clintondale

Other great vacation rentals in Poughkeepsie

Loft in New Paltz

Apartment in Millbrook

Apartment in Hyde Park

Home in Poughkeepsie

Apartment in Poughkeepsie

Apartment in Arlington

Apartment in Poughkeepsie

Yurt in Poughkeepsie

Quick stats about vacation rentals in Poughkeepsie

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Poughkeepsie?

Are there pet-friendly vacation rentals in Poughkeepsie?

How much does it cost to stay in house rentals in Poughkeepsie?

Do house rentals in Poughkeepsie have a bbq area?

Do apartment rentals in Poughkeepsie have wifi?

Do house rentals in Poughkeepsie have air conditioning?

Are there family-friendly house rentals in Poughkeepsie?

What are the most popular amenities for House Rentals in Poughkeepsie?

Destinations to explore