Montgomery, NY Vacation Homes from ￥20,693

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Our top choices for Montgomery vacation homes

A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

1. Luxury 3BR with King Beds in Montgomery Village

Montgomery

Barbara M.

￥76,605 total

includes taxes & fees

Sep 14 - Sep 15

A modern kitchen with white cabinetry, a central island with stools, a built-in oven, and a stainless steel refrigerator.

2. New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!

Montgomery

Kyle F.

￥214,429 total

includes taxes & fees

Sep 14 - Sep 15

A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

3. Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

wallkill

Debbie M.

￥63,328 total

includes taxes & fees

Sep 29 - Sep 30

A modern living room with a fireplace, a dining area with a wooden table, and a large window with curtains.

4. Zen House at the Mountain Ridge

Gardiner

Julie

￥32,633 total

includes taxes & fees

Sep 14 - Sep 15

A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

5. The DeVita House Est. 1900

Gardiner

Christopher T.

￥68,474 total

includes taxes & fees

Sep 15 - Sep 16

A modern kitchen with a built-in microwave and a dining area with a table and chairs.

6. The Columbus Hotel - The Courtyard Suite - 89-303

Middletown

￥34,057 total

includes taxes & fees

Sep 15 - Sep 16

A forest campsite with a tent, a fire pit, and a bench.

7. Glamping Tent & Campsite by Minnewaska State Park

Kerhonkson

Andie C.

￥23,312 total

includes taxes & fees

Sep 13 - Sep 14

A lakeside view with a picnic table and chairs, a grill, and a clear sky.

8. Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains

wallkill

Dauna A.

￥88,481 total

includes taxes & fees

Sep 28 - Sep 29

A kitchen with wooden shelves, a window with a view of trees, and a vase with flowers on the windowsill.

9. Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Kerhonkson

Sueane

￥28,583 total

includes taxes & fees

Sep 17 - Sep 18

A fireplace with logs, a vase with flowers, and candles on a woven mat.

10. Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Kerhonkson

jwinegra W.

￥32,398 total

includes taxes & fees

Sep 23 - Sep 24

A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

11. Hike & Fish: Outdoor Retreat Near Trails

Wurtsboro

Nate R.

￥58,910 total

includes taxes & fees

Sep 13 - Sep 14

A deck with Adirondack chairs, a fire pit, and a grill.

12. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

Cornwall

Elisabeth

￥61,513 total

includes taxes & fees

Sep 14 - Sep 15

A modern kitchen with a white island, stainless steel appliances, and wooden flooring.

13. Bright Contemporary Near The Best Hiking Trails

Pine Bush

Amy L.

￥89,505 total

includes taxes & fees

Sep 22 - Sep 23

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a round table and chairs.

14. Ranch Home with Game Room, Fire Pit & Near Trails

New Paltz

Margaret

￥70,513 total

includes taxes & fees

Sep 13 - Sep 14

A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

15. House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls

Scott G.

￥61,451 total

includes taxes & fees

Sep 14 - Sep 15

A bedroom with a bed, a TV mounted on the wall, a window with a view of greenery, and a small seating area with a table and chairs.

16. The Studio at the Inn at High Falls

High Falls

Jia

￥41,548 total

includes taxes & fees

Sep 14 - Sep 15

A bedroom with a large bed, a window with a view of trees, and an open door leading to a patio.

17. Private Forest Estate - Pool · Theater · Game Room . Sleep 18

Pine Bush

"Just returned from a 3 generation family celebration. This house was exactly as described. So beautiful, had all the amenities. More areas to relax, party, or just enjoy. The pool and pool house were just amazing. Kitchen and dining areas were great to work and enjoy. Basement had so many games to choose from. We already planning a return. Liliana was a terrific host, she responded to all our requests within minutes. Thank you so much."

Greta U.

￥191,375 total

includes taxes & fees

Sep 22 - Sep 23

A window with a view of a green, leafy outdoor area, possibly a garden or park.

18. Trails Head Tiny House

Rock Hill

Michael R.

￥20,693 total

includes taxes & fees

Sep 13 - Sep 14

A hot tub in a lush garden with a stone wall and outdoor furniture.

19. Country House w/Hot Tub, Deck, Grill & Fire Pit

Goshen

Mike T.

￥88,357 total

includes taxes & fees

Sep 15 - Sep 16

A room with a chandelier, a sofa, a table, and a cabinet.

20. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Warwick

Paul E.

￥23,825 total

includes taxes & fees

Sep 14 - Sep 15

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Top Montgomery Hotel Reviews

Overlook Lodge at Bear Mountain

8/10 Good

"This location and its history made this Inn a great stopover night for us as we travelled down the East Coast. The scenery is beautiful and the staff are helpful and friendly. This would would be a great place to meet with family members and/or friends to enjoy sharing a cottage (with 6 rooms and a common area) to enjoy a few nights or week together. There is a lot to do in the area and the porch of the cottage lends itself to just sitting and admiring the natural surroundings, especially the lake!"

Hampton Inn by Hilton New Paltz

8/10 Good

"We had a beautiful time at Hampton Inn. The only trouble we had, was whoever was staying in the room above us was terribly loud. It had nothing to do with the hotel though. The staff were kind and friendly and accommodating. The pool was nice, wish it was a bit warmer, but that's just me. Wonderful time! This was our 4th time staying at this hotel. Close to shops, restaurants, and Minnewaska State Park for hiking. We will be back soon!"

Holiday Inn Express Poughkeepsie by IHG

8/10 Good

"Parking was super easy with plenty of spaces available at the entrances. The room was clean and relatively quiet. Because the hotel is off the highway there wasn't a lot of road noise. The hallways show a lot of wear and tear but if you get past this aspect and into your room all is acceptable."

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent

"This Red Roof Inn is very clean and the staff is friendly. Minor complain is that the floors feels like there is a film on it that feels a bit slippery, probably from build up of cleaning agent, but room is clean. I enjoyed my stay."

Super 8 by Wyndham Montgomery Maybrook

8/10 Good

"It was definitely a budget motel. They were in the process of renovations, which are definitely needed. It's not the place for a romantic getaway or relaxing weekend, but ok for a nights sleep. The staff was super friendly and they appeared to be working on improvements. So gave them consideration for that."

Find out more about Montgomery

Montgomery Vacation Homes information

Number of reviews	373
Accommodation	402 Vacation Homes
Lowest Price	￥20,693
Highest Price	￥214,429

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Montgomery vacation homes

1. Luxury 3BR with King Beds in Montgomery Village

2. New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!

3. Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

4. Zen House at the Mountain Ridge

5. The DeVita House Est. 1900

6. The Columbus Hotel - The Courtyard Suite - 89-303

7. Glamping Tent & Campsite by Minnewaska State Park

8. Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains

9. Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

10. Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

11. Hike & Fish: Outdoor Retreat Near Trails

12. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

13. Bright Contemporary Near The Best Hiking Trails

14. Ranch Home with Game Room, Fire Pit & Near Trails

15. House on the Babbling Brook- Quiet 2BR + King Bed!

16. The Studio at the Inn at High Falls

17. Private Forest Estate - Pool · Theater · Game Room . Sleep 18

18. Trails Head Tiny House

19. Country House w/Hot Tub, Deck, Grill & Fire Pit

20. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Find vacation rentals that suit your style

Top Montgomery Hotel Reviews

Overlook Lodge at Bear Mountain

Hampton Inn by Hilton New Paltz

Sleep Inn & Suites Monroe - Woodbury

Fairfield Inn & Suites by Marriott Goshen Middletown

Holiday Inn Express Poughkeepsie by IHG

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Super 8 by Wyndham Montgomery Maybrook

Find out more about Montgomery

Montgomery Vacation Homes information

Explore a world of travel with Expedia

Search Vacation Homes in Montgomery

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Montgomery vacation homes

1. Luxury 3BR with King Beds in Montgomery Village

2. New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!

3. Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

4. Zen House at the Mountain Ridge

5. The DeVita House Est. 1900

6. The Columbus Hotel - The Courtyard Suite - 89-303

7. Glamping Tent & Campsite by Minnewaska State Park

8. Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains

9. Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

10. Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

11. Hike & Fish: Outdoor Retreat Near Trails

12. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

13. Bright Contemporary Near The Best Hiking Trails

14. Ranch Home with Game Room, Fire Pit & Near Trails

15. House on the Babbling Brook- Quiet 2BR + King Bed!

16. The Studio at the Inn at High Falls

17. Private Forest Estate - Pool · Theater · Game Room . Sleep 18

18. Trails Head Tiny House

19. Country House w/Hot Tub, Deck, Grill & Fire Pit

20. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Find vacation rentals that suit your style

Top Montgomery Hotel Reviews

Overlook Lodge at Bear Mountain

Find out more about Montgomery

Montgomery Vacation Homes information

Explore a world of travel with Expedia