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Vacation rentals in Montgomery

Vacation rentals in Montgomery

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Montgomery

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

  • Garden View Guest Cottage
    SUPERHOSTEntire guest suite · 6 guests · 3 beds · 2 baths
    Garden View Guest Cottage

    Located under 15 min.from Stewart Airport...minutes to Angry Orchards and half 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...It's 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

    What guests are saying:

    “Lambrini’s place is outstanding. It was a perfect stay for our needs. We wanted a quiet get away with all the amenities of home, and this well sized cottage is exactly that. Private, adorably quaint, and stocked with everything we needed! We were able to cook full meals with all the kitchen items we could have asked for. It was such a convenience to be able to clean our clothes in a spacious and stocked laundry area. Quiet residential neighborhood with easy walking in the immediate area. Lambrini’s communication was perfect, and she was wonderfully helpful and attentive without infringing upon our privacy in any way. She is truly a kind and wonderful host. This has been the most pleasant and stress free AirBNB experience we have had. Thank you so much Lambrini.”

  • 5-Star Certified Inn - King Suite
    SUPERHOSTHotel room · 2 guests · 1 bed · 1 bath
    5-Star Certified Inn - King Suite

    Welcome to the only BNB located in the center of Montgomery Village. Get that rural feel while being able to walk to restaurants and shops. Close drive to Angry Orchard, Shawangunk Wine Trail, Hiking, U-Pick Farms, Storm King Sculpture Park and many other wonders of the Hudson Valley! The stately "MONTGOMERY" room, the original master bedroom of the Borland House built in 1839, has a king-size bed and private bathroom. You can also enjoy brunch in our award winning restaurant (not included).

    What guests are saying:

    “The Borland House was so comfy and cute! We absolutely loved our stay there and my fiancé and I agree it is one of our favorite places we’ve stayed. The bed was incredibly comfortable, everything was sparkling clean and brunch the next morning in the downstairs restaurant was out of this world. We were in town to visit Angry Orchard and the Airbnb was located perfectly just ten minutes away. The only thing we didn’t care for was the bathroom located outside of the bedroom but we were left robes in our room and it proved not to be a big deal.”

  • ☆ 30' Travel Trailer 2 Bedrooms, No Cleaning Fees
    SUPERHOSTCamper/RV · 6 guests · 4 beds · 1 bath
    ☆ 30' Travel Trailer 2 Bedrooms, No Cleaning Fees

    30' Travel Trailer In Wallkill. Near Stewart Airport, New Paltz, Newburgh, and Rail Trail. Even though the space can sleep 9, it is a small space, small bathroom and is ideally suited for six. Front bedroom has accordion folding doors, with a Queen bed that sleeps two. Back bedroom has a curtain door, and sleeps 4: two on top bunks and two on the folding floor sofa. The living room sofa also opens to sleep two, and the dinette table drops to create an additional sleeping area.

    What guests are saying:

    “We had a great stay! The space is very comfortable, cozy and nicely fits our family of 4. Arrival was super smooth, and the space included everything that we needed to make basic meals (bring your own Tupperware, foil, etc if you need to get deeper in to cooking/storage). In addition to great accommodations, we felt very safe here. We are lucky to be well acquainted with navigating RV accommodations, however George and Kelly were available immediately any time we had a question. We come to town regularly for military reserve duty, and plan on booking stays here any time we can. Thank you again!”

Vacation rentals for every style

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Popular amenities for Montgomery vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Montgomery

Charming little cabin
SUPERHOSTEntire cabin
Charming little cabin
Price:€90 / night
Just Around The Corner
SUPERHOSTEntire apartment
Just Around The Corner
Price:€94 / night
**Walton Lake Camper** close to Woodbury Commons
SUPERHOSTCamper/RV
**Walton Lake Camper** close to Woodbury Commons
Price:€58 / night
Stunning 1 bedroom apartment on quiet street
SUPERHOSTEntire apartment
Stunning 1 bedroom apartment on quiet street
Price:€86 / night
1830's Farm House, Private Room & Bath
SUPERHOSTPrivate room
1830's Farm House, Private Room & Bath
Price:€67 / night
Cabin in the heart of the Hudson Valley, Cabin 2
SUPERHOSTTiny house
Cabin in the heart of the Hudson Valley, Cabin 2
Price:€71 / night
King Suite with Claw Foot Tub in Historic Mansion
SUPERHOSTPrivate room
King Suite with Claw Foot Tub in Historic Mansion
Price:€76 / night
#2, Quaint Private Apartment in Historic Building
SUPERHOSTEntire apartment
#2, Quaint Private Apartment in Historic Building
Price:€90 / night
Amazing Grace Farm
SUPERHOSTPrivate room
Amazing Grace Farm
Price:€67 / night
Hudson Valley Beacon West Point “SWF” nearby #1
SUPERHOSTPrivate room
Hudson Valley Beacon West Point “SWF” nearby #1
Price:€155 / night
Fern - Kos Retreats @ Frogs Hollow Farm
SUPERHOSTYurt
Fern - Kos Retreats @ Frogs Hollow Farm
Price:€202 / night
Seclusion and romance, most popular airbnb around
SUPERHOSTEntire cottage
Seclusion and romance, most popular airbnb around
Price:€264 / night
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