Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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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.

Oct 8 – 15

G$29,411 GYD 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!

Sep 15 – 22

G$32,520 GYD per night

Guest favorite

Loft in New Paltz

4.94 out of 5 average rating, 205 reviews

Cozy Couples Retreat w/ Short Walk Into New Paltz

Come enjoy our quiet studio retreat just a short walk to town, SUNY college and beautiful nature trails. If you're looking to escape the city or to visit a college friend, this is the perfect studio apartment for couples or solo travelers to relax in after a day of exploring the historic town of New Paltz. - 5 Min Walk to Millbrook Nature Preserve - 15 Min Walk to Main St. - 20 Min Walk From Bus Station - Short Drive to Mohonk, River to Ridge & Minnewaska *Sleeps Up To 4 (pullout sofa)

Dec 4 – 11

G$26,609 GYD per night

Guest favorite

Apartment in New Paltz

4.96 out of 5 average rating, 346 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

G$23,841 GYD per night

Guest favorite

Home in Hyde Park

4.86 out of 5 average rating, 182 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.

Mar 19 – 26

G$21,227 GYD per night

Guest favorite

Apartment in New Paltz

4.83 out of 5 average rating, 339 reviews

Fun, Private, Cozy, Tiny House

You’ve seen them on TV, this is your chance to experience tiny house living 1st-hand :) All the amenities you need to have a most relaxing and joyful time: heat, A/C, Wifi, queen bed, kitchen, shower, hot water, private patio + fire place. Centrally located in New Paltz. Walking distance to the rail tail, Nyguist nature preserve, Huguenot Street, restaurants, bars, cafes and galleries. 20 mins to Mohonk, Gunks, Minnewaska, Skytop Tower, Kingston, 30 mins to Woodstock, Saugerties,

May 8 – 15

G$17,463 GYD per night

Guest favorite

Cabin in Highland

4.92 out of 5 average rating, 461 reviews

Country Log Home Retreat

This authentic log home is a beautiful, comfortable country getaway with all the amenities you desire. The house is nestled between the magnificent Shawangunk Mountains, affectionately called “the Gunks,” and the majestic Hudson River. It is set in a country landscape yet close to New Paltz - so you can have the best of both worlds. My home is perfect for hiking, site seeing or just relaxing. New Paltz is 10 minutes away by car, the Gunks and hiking are 15 minutes away.

Jun 27 – Jul 4

G$45,456 GYD per night

Guest favorite

Guest suite in New Paltz

4.99 out of 5 average rating, 105 reviews

New Paltz Charmer

Your Hudson Valley haven in historic New Paltz: Relax & unwind in a spacious, newly-renovated 1-bedroom apartment with a sunny living room/kitchenette nestled in a quiet neighborhood not far from Main Street restaurants & shopping. You'll have the 2nd floor of a 2-story house, bordered by majestic trees, all to yourself, including a private entrance. Excellent biking and hiking trails are within steps of the house; more hiking, swimming, and rock climbing are a short drive away.

May 30 – Jun 6

G$26,587 GYD per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 742 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 13 – 20

G$22,914 GYD 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.

Sep 29 – Oct 6

G$34,642 GYD per night

Guest favorite

Apartment in New Paltz

4.89 out of 5 average rating, 231 reviews

Homey Haven:Inviting Airbnb Suite with kitchen

Our private apartment is within a charming cape cod house with everything you need for a getaway to the Hudson Valley. Approximately 425 sq ft. apartment includes a bedroom, bathroom and eat in kitchen. 1 mile from center of New Paltz and 5 minutes walk to rail trail and Huguenot street. Bedroom has queen size bed, 40" flat screen smart tv. Full kitchen with everything you need and parking for up to 2 cars. Patio area has two chairs and a gas grill.

Jul 15 – 22

G$19,514 GYD per night

Guest favorite

Apartment in New Paltz

4.98 out of 5 average rating, 425 reviews

The Treehouse, lush Parisian inspired Studio

The Treehouse, a lush Parisian inspired Studio high in the treetops in the heart of the village of New Paltz. Private entrance leading to private rooftop deck, lovely sun filled space to enjoy the treescape or sunset. The Treehouse strives to be more than a place to sleep. If you’re looking for a place that will move your heart as well as place to call home while staying in New Paltz please consider The Treehouse.

Sep 16 – 23

G$27,783 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Highland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Highland's top sights

Hannaford Supermarket33 locals recommend

Gateway Diner6 locals recommend

Dunkin'14 locals recommend

Underground Coffee & Ales23 locals recommend

Franny Reese State Park25 locals recommend

Shamrock Wine & Liquor4 locals recommend

Other great vacation rentals in Highland

Guest favorite

Apartment in New Paltz

4.93 out of 5 average rating, 280 reviews

Sweet Suite on Beautiful Mountain Road *Pool*

May 8 – 15

G$25,427 GYD per night

Guest favorite

Home in Kingston

4.97 out of 5 average rating, 276 reviews

This New House

Jan 13 – 20

G$30,114 GYD per night

Guest favorite

Cottage in West Park

4.84 out of 5 average rating, 195 reviews

Rustic, Sunny, Little Red Cottage in the Woods

Aug 9 – 16

G$25,303 GYD per night

Guest favorite

Apartment in New Paltz

5.0 out of 5 average rating, 106 reviews

Hike in New Paltz and stay at escape to the gunks!

Jul 17 – 24

G$31,058 GYD per night

Guest favorite

Condo in Poughkeepsie

4.97 out of 5 average rating, 224 reviews

Spacious and stylish entire one bedroom apartment.

Jul 8 – 15

G$28,821 GYD per night

Guest favorite

Tiny home in Marlboro

4.96 out of 5 average rating, 280 reviews

Orchard Views from a Light-Filled Tiny Home with a Fire Pit

Dec 30 – Jan 6

G$31,154 GYD per night

Guest favorite

Tiny home in Marlboro

4.93 out of 5 average rating, 219 reviews

Cozy 1860's Cottage Near Weeds Orchards,Glorie Fms

Mar 18 – 25

G$25,746 GYD per night

Guest favorite

Tiny home in Highland

4.96 out of 5 average rating, 48 reviews

A delightful and cozy studio retreat.

Jun 2 – 9

G$16,436 GYD per night

Show all

Quick stats about vacation rentals in Highland

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
760 reviews
Nightly prices starting at
G$8,339 GYD before taxes and fees

Frequently Asked Questions

Do house rentals in Highland have wireless internet?
Absolutely! We offer over 10 house rentals with wireless internet in Highland. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Highland?
Highland has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Highland?
Experience the best of Highland 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.
Are there vacation rentals with a dedicated workspace in Highland?
Yes! Work meets play with ease at over 10 vacation rentals in Highland featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Highland

Top-rated vacation rentals in Highland

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Highland vacation rentals

Stay near Highland's top sights

Other great vacation rentals in Highland

Apartment in New Paltz

Home in Kingston

Cottage in West Park

Apartment in New Paltz

Condo in Poughkeepsie

Tiny home in Marlboro

Tiny home in Marlboro

Tiny home in Highland

Quick stats about vacation rentals in Highland

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Highland have wireless internet?

Are there family-friendly vacation rentals in Highland?

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

Are there vacation rentals with a dedicated workspace in Highland?

Destinations to explore