Vacation rentals in Montgomery

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Top-rated vacation rentals in Montgomery

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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

Guest suite in Montgomery

4.95 out of 5 average rating, 420 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Nov 5 – 12

G$26,892 GYD per night

Guest favorite

Farm stay in Montgomery

4.93 out of 5 average rating, 341 reviews

The Step by 127 Cabin Co.

Looking for a night out to relax and escape the hustle and bustle? The Step is a small custom built A-Frame designed for those looking for a simple & memorable stay. Whether you are looking for a quiet night under the stars or a space to unwind while being off the grid, The Step is a great place for you to experience all that nature has to offer. The cabin is private & secluded located on farmland. Just 3 minutes from town with great local restaurants, pickle ball, & more *Please Note No Shower

Jul 8 – 15

G$41,804 GYD per night

Guest favorite

Guest suite in Chester

4.95 out of 5 average rating, 230 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, and has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, a French door shower, and a kitchenette with sunny breakfast nook. It is freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Jun 15 – 22

G$22,302 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

Cottage in Newburgh

4.88 out of 5 average rating, 186 reviews

Cozy Lake Cottage

Cozy cottage in residential lake community, adjacent to historic fine dining restaurant. There is an approximate 150 yard walk down to the lake to enjoy the spectacular sunsets . Centrally located in the Hudson Valley near everything there is to experience. Located in our area Many Local Wineries ( Angry Orchard) Orange County Choppers Cafe Woodbury Commons Outlet Mall Historic Newburgh and Waterfront Culinary Institute of America US Military Academy New Paltz and Mohonk Mountain House

May 27 – Jun 3

G$26,857 GYD per night

Guest favorite

Cottage in Goshen

4.94 out of 5 average rating, 194 reviews

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

Jan 5 – 12

G$27,938 GYD per night

Guest favorite

Apartment in Marlboro

4.97 out of 5 average rating, 309 reviews

Cliff Top at Turtle Rock

Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

Mar 11 – 18

G$25,842 GYD per night

Guest favorite

Tiny home in Wallkill

4.99 out of 5 average rating, 204 reviews

Get Away to "Hygge" Tiny House on 75 Private Acres

Escape to 75 acres of secluded, private land and lounge in this "hyggelig" tiny house. The house has everything you need, from heat and A/c, strong wifi, TV with streaming (sign in to Netflix, HBO, etc), full working kitchen (gas stove, oven, microwave), shower and bathroom. This tiny house has an incredible amount of light coming in from the very large windows throughout. Outdoor amenities include wood patio, grill, dining table/chairs, fire pit. Lawn games available on request.

Jun 29 – Jul 6

G$43,960 GYD per night

Guest favorite

Apartment in Newburgh

4.93 out of 5 average rating, 213 reviews

ECO MCM GEM- central to Bethels & West Point

Fab Mid-Century Eco friendly apartment is all you need for a relaxing Hudson Valley Retreat! Close proximity to all Hiking areas , Storm King, West Point, Beacon DIA , Newburgh Assembly (8 min) and centrally located to all Bethel facilities Wallkill,Patterson and Warwick. This cozy two bedroom downstairs walkout apartment is tucked away and sits amongst the trees with large windows to enjoy nature. Also, features a large private patio , table, chimnea fireplace and BBQ.

Jul 18 – 25

G$27,701 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 New Paltz

4.97 out of 5 average rating, 677 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

Jan 21 – 28

G$27,376 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Montgomery vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Montgomery's top sights

City Winery Hudson Valley46 locals recommend

Copperfields Kildare Pub6 locals recommend

Ward's Bridge Inn18 locals recommend

Iron Cafe10 locals recommend

wildfire grill6 locals recommend

The Table3 locals recommend

Other great vacation rentals in Montgomery

Guest favorite

Loft in Cornwall

4.86 out of 5 average rating, 393 reviews

Country Getaway - Close to Hiking & Storm King

Mar 15 – 22

G$18,985 GYD per night

Guest favorite

Guesthouse in Olivebridge

4.97 out of 5 average rating, 224 reviews

Black Olive Cabin in the Woods - Secluded, Tiny

Aug 5 – 12

G$31,701 GYD per night

Guest favorite

Guest suite in Newburgh

4.92 out of 5 average rating, 165 reviews

Hudson River Views-romantic getaway close to NYC

Nov 24 – Dec 1

G$24,481 GYD per night

Guest favorite

Apartment in Newburgh

4.84 out of 5 average rating, 113 reviews

Special Nest w Private Entrance River View Porches

Sep 17 – 24

G$27,317 GYD per night

Guest favorite

Guest suite in Newburgh

4.93 out of 5 average rating, 446 reviews

Glenbrook Country Villa

Feb 27 – Mar 6

G$27,833 GYD per night

Guest favorite

Home in Montgomery

5.0 out of 5 average rating, 7 reviews

Escape to serenity at the Pullman Cottage

May 4 – 11

G$26,116 GYD per night

Guest favorite

Guesthouse in Middletown

5.0 out of 5 average rating, 10 reviews

Hudson Valley Retreat on 8 Acres

Sep 10 – 17

G$37,883 GYD per night

Guest favorite

Guesthouse in Montgomery

5.0 out of 5 average rating, 19 reviews

The Cottage

Jun 12 – 19

G$32,111 GYD per night

Show all

Quick stats about vacation rentals in Montgomery

Total rentals
10 properties
Local attractions
City Winery Hudson Valley, Copperfields Kildare Pub, and Ward's Bridge Inn
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
880 reviews
Nightly prices starting at
G$18,764 GYD before taxes and fees

Vacation rentals in Montgomery

Top-rated vacation rentals in Montgomery

Farm stay in New Paltz

Guest suite in Montgomery

Farm stay in Montgomery

Guest suite in Chester

Apartment in New Paltz

Cottage in Newburgh

Cottage in Goshen

Apartment in Marlboro

Tiny home in Wallkill

Apartment in Newburgh

Tiny home in New Paltz

Home in New Paltz

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Montgomery vacation rentals

Stay near Montgomery's top sights

Other great vacation rentals in Montgomery

Loft in Cornwall

Guesthouse in Olivebridge

Guest suite in Newburgh

Apartment in Newburgh

Guest suite in Newburgh

Home in Montgomery

Guesthouse in Middletown

Guesthouse in Montgomery

Quick stats about vacation rentals in Montgomery

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore