Montgomery holiday rentals

We found 128 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Montgomery to find one that's perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a pool. You're sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Montgomery

Showing deals for:27 Nov - 4 Dec

Property grounds
Interior
Exterior
Private kitchen
Exceptional
(5 reviews)

Brand new Ski Chalet 4 miles to Jay Peak

North Troy

8% off
AU$6,068
for 7 nights, 1 chalet
AU$867 per night
includes taxes & fees
Brand new Ski Chalet 4 miles to Jay Peak
Main living room with gas fireplace and hot tub outside
First tracks accessible - Nothing like it!
Large main living area
Fully equipped kitchen
Exceptional
(65 reviews)

Skiers and Golfers Paradise - Ski In/Ski Out with private hot tub and steam room

North Troy

8% off
AU$8,807
for 7 nights, 1 home
AU$1,258 per night
includes taxes & fees
Skiers and Golfers Paradise - Ski In/Ski Out with private hot tub and steam room
clubhouse dining
water park
facilities
18 hole championship golf
Exceptional
(24 reviews)

Lux 5BR/4BA V125 Ski I/O, 18-hole Championship Golf, Water Park, pet friendly

North Troy

12% off
AU$8,622
for 7 nights, 1 home
AU$1,232 per night
includes taxes & fees
Lux 5BR/4BA V125 Ski I/O, 18-hole Championship Golf, Water Park, pet friendly
The informal dining area and its fireplace to keep you warm in the Winter
View of formal dining area and loft opening
Coolest room in the house
Welcome to our kitchen.
Exceptional
(80 reviews)

Rustic Vermont Barn Home Near Jay Peak w/Pizza Oven

Montgomery Center

8% off
AU$3,807
for 7 nights, 1 home
AU$544 per night
includes taxes & fees
Rustic Vermont Barn Home Near Jay Peak w/Pizza Oven
Private kitchen
Room
Property grounds
Interior
Exceptional
(46 reviews)

Charming cottage by Jay Peak

Montgomery Center

8% off
AU$2,044
for 7 nights, 1 cottage
AU$292 per night
includes taxes & fees
Charming cottage by Jay Peak
Kitchen from the bedrooms side
Exterior
Kitchen
living room
Exceptional
(6 reviews)

Beautiful chalet close to Jay Peak resort

Montgomery Center

16% off
AU$2,809
for 7 nights, 1 home
AU$401 per night
includes taxes & fees
Beautiful chalet close to Jay Peak resort
Summer setting, property surrounded by Maple, Birch, and Hemlock
Custom Kitchen w/Granite complete with real Pebble Backsplash
Cozy living room with wood burning fireplace
Wrought iron wood fireplace with 12' stone hearth, watch Tram out windows!
Exceptional
(95 reviews)

Best Ski In/Ski Out Location - ❄️❄️ Jay Peak Large 3 BR

North Troy

8% off
AU$6,205
for 7 nights, 1 apartment
AU$886 per night
includes taxes & fees
Best Ski In/Ski Out Location - ❄️❄️ Jay Peak Large 3 BR
Ski In/Out Access via Grammy Jay Trail
Pump House Water Park
Living Room
Village Condo Exterior
Exceptional
(86 reviews)

Great Family Getaway! Ski-In Ski-Out Luxury Condo at Jay Peak Resort.

North Troy

8% off
AU$3,816
for 7 nights, 1 apartment
AU$545 per night
includes taxes & fees
Great Family Getaway! Ski-In Ski-Out Luxury Condo at Jay Peak Resort.
All new Appliances with Premium Quartz Countertop
Cozy Great Room with Propane Fireplace — The perfect place to relax after a full day skiing Jay Peak’s legendary powder.
Open-Concept Great Room, Dining Room and Kitchen - Plenty of space for everyone to spread out
Fully stocked kitchen designed for real cooking — ideal for family breakfasts before first chair or relaxed dinners after the slopes.
Exceptional
(7 reviews)

Best Location @ Jay: Remodeled, Ski-in/Out by Waterpark, Ice Rink, A/C & Dogs OK

North Troy

8% off
AU$4,608
for 7 nights, 1 apartment
AU$658 per night
includes taxes & fees
Best Location @ Jay: Remodeled, Ski-in/Out by Waterpark, Ice Rink, A/C & Dogs OK
Private kitchen
Interior
Dining
A peaceful and beautiful spot for summer too!
Exceptional
(216 reviews)

Spacious ski-in, ski-out 2-BR Jay Peak Village Condo, right on trail. A/C incl.!

North Troy

7% off
AU$1,886
for 7 nights, 1 apartment
AU$269 per night
includes taxes & fees
Spacious ski-in, ski-out 2-BR Jay Peak Village Condo, right on trail. A/C incl.!
Master bedroom (Main floor) view from windows
Waterpark at the Jay Hotel
Front door to main floor (Left). Front door to lower level entryway (Right)
Main Floor Kitchen
Exceptional
(86 reviews)

Ski-in, ski-out Village Condo at Jay Peak Resort

North Troy

8% off
AU$3,768
for 7 nights, 1 apartment
AU$538 per night
includes taxes & fees
Ski-in, ski-out Village Condo at Jay Peak Resort
Dining
Private kitchen
Interior
Interior
Exceptional
(22 reviews)

Circa 1850s fully renovated Vermont farmhouse less than 15 miles from Jay Peak

Richford

8% off
AU$4,290
for 7 nights, 1 home
AU$613 per night
includes taxes & fees
Circa 1850s fully renovated Vermont farmhouse less than 15 miles from Jay Peak
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Montgomery getaway

Learn about the unique charm of Montgomery with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Montgomery

Are you hoping to discover attractions to see in the city? Venture out of your cosy holiday rental and experience everything that Montgomery has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Jay Peak Ski Resort (6.3 mi / 10.1 km)
  • Pump House Indoor Waterpark (7 mi / 11.3 km)
  • Jay Peak Resort Golf Course (7.3 mi / 11.7 km)
  • Chapelle Ste Agnes Vineyard (8.9 mi / 14.3 km)
  • Sutton Natural Environment Park (14.2 mi / 22.8 km)
  • Mont Sutton (14.4 mi / 23.2 km)

Exploring the natural features in Montgomery

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Montgomery is a great place to get outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Jay Peak (5.8 mi / 9.3 km)
  • Lake Carmi (12.5 mi / 20.1 km)
  • Lake Eden (14.2 mi / 22.9 km)
  • Lamoille Valley Rail Trail (19.8 mi / 31.8 km)
  • Long Trail State Forest (6.7 mi / 10.8 km)
  • Park Mansonville (15.9 mi / 25.5 km)

Transport options to and around Montgomery

Fly into Newport, VT (EFK-Newport State), the closest airport, located 20.3 mi (32.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Stowe, VT (MVL-Morrisville-Stowe State), which is 25.2 mi (40.6 km) away.

Frequently asked questions

Are there holiday rentals in Montgomery?
Yes, there are holiday rentals close to the most popular sights in Montgomery, or you can select a more secluded option if you're looking for a relaxing stay.
What can I see and do in Montgomery?
Explore the area and family-friendly sights such as Pump House Indoor Waterpark, or get out into nature at a spot like Jay Peak. In the wider area, you'll find Jay Peak Ski Resort and Jay Peak Resort Golf Course.
What are holiday rentals like in Montgomery?
Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Montgomery. Holiday rentals feature amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family gatherings.