Montgomery Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

2.5 out of 5
2105 Route 208 Montgomery NY
2.63 km from city center
Book a stay at this business-friendly hotel in Montgomery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
207 Montgomery Rd Montgomery NY
2.92 km from city center
Book a stay at this business-friendly motel in Montgomery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Borland House Inn

Borland House Inn

3 out of 5
130 Clinton Street Montgomery NY
0.13 km from city center
Book a stay at this business-friendly B&B in Montgomery. Enjoy free breakfast, free WiFi, and free parking. Popular attractions City Winery Hudson Valley and ...
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
555 Resorts World Drive Monticello NY
38.01 km from city center
Book a stay at this family-friendly hotel in Monticello. Enjoy 5 restaurants, 2 bars/lounges, and water park access (surcharge). Our guests praise the helpful ...
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
888 Resorts World Drive Monticello NY
37.32 km from city center
Book a stay at this luxury hotel in Monticello. Enjoy a full-service spa, 6 restaurants, and a casino. Our guests praise the helpful staff and the clean rooms ...
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
20.02 km from city center
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
29.02 km from city center
Book a stay at this golf hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
29.03 km from city center
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
24 Crystal Run Xing Middletown NY
14.03 km from city center
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
30.87 km from city center
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 out of 5
60 Centre Dr Central Valley NY
25.26 km from city center
Book a stay at this business-friendly hotel in Central Valley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
28.77 km from city center
Book a stay at this golf hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Courtyard by Marriott Fishkill

Courtyard by Marriott Fishkill

3 out of 5
17 Westage Drive Fishkill NY
28.64 km from city center
Book a stay at this business-friendly hotel in Fishkill. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St Gardiner NY
18.69 km from city center
Book a stay at this luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tuthilltown Spirits and DM Weil Gallery ...
Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

2.5 out of 5
4 South Putt Corners Road New Paltz NY
27.56 km from city center
Book a stay at this business-friendly hotel in New Paltz. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
Don't see what you're looking for?
See all available properties in Montgomery
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Wed, May 20 - Wed, May 27
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$137 Roundtrip, found 4 days ago
$137
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, May 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, May 27, priced at $137 found 4 days ago
Breeze Airways
Wed, May 20 - Wed, May 27
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$142 Roundtrip, found 4 days ago
$142
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, May 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, May 27, priced at $142 found 4 days ago
Breeze Airways
Wed, May 20 - Wed, May 27
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$147 Roundtrip, found 4 days ago
$147
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, May 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, May 27, priced at $147 found 4 days ago
Breeze Airways
Wed, May 20 - Wed, May 27
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$152 Roundtrip, found 1 day ago
$152
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, May 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, May 27, priced at $152 found 1 day ago