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Montgomery Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Montgomery holiday rentals

A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

1. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"The room was very clean and modern. The check-in process was easy and I had the best rest that I had in a long time. Being in the lower level with no windows provided a very quiet and dark ambiance at night. There is ample lighting throughout the unit if needed though, you can really unplug here. I would definitely stay here again"
United States
Kebreab H.
The price is AU$350
includes taxes & fees
29 Sept - 30 Sept
Modern Studio Ideal for Traveling Professionals

2. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"Closer to downtown able to"
United States
Jeremy R.
The price is AU$496
includes taxes & fees
29 Sept - 30 Sept
Work, Play & Stay! Apt Near Holyoke Medical Center
A house with a porch, a garden with pink flowers, and a stone wall along the road.

3. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (152 reviews)
"Great location"
United States
Will G.
The price is AU$495
includes taxes & fees
6 Oct - 7 Oct
Big farmhouse in the foothills of the Berkshires
A cozy room with two beds, large windows, and a view of a snowy landscape.

4. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (77 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is AU$400
includes taxes & fees
29 Sept - 30 Sept
The Creation Station is a cozy place so make yourself at home.
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

5. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is AU$339
includes taxes & fees
29 Sept - 30 Sept
Modern Studio Ideal for Traveling Professionals
A living room with a fireplace, a sofa, a coffee table, and a TV.

6. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (11 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is AU$343
includes taxes & fees
29 Sept - 30 Sept
Cozy 2-bedroom apartment in Chicopee
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

7. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$528
includes taxes & fees
29 Sept - 30 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A living room with a sofa set, a coffee table, and two lamps.

8. Cozy First Floor Apartment. Located in a quiet neighborhood.

Cozy First Floor Apartment. Located in a quiet neighborhood.
Chicopee
9.6 out of 10, Exceptional, (12 reviews)
"Check in was very easy. The apartment had all the necessities in the kitchen and bathroom. Location was convenient and the neighborhood very safe/quiet."
United States
Morrris
The price is AU$441
includes taxes & fees
29 Sept - 30 Sept
Cozy First Floor Apartment. Located in a quiet neighborhood.
A square fire pit with flames, surrounded by a grassy field and a green chair.

9. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (24 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is AU$266
includes taxes & fees
5 Oct - 6 Oct
Peaceful Meadow Retreat
A hot tub with a string of lights above it, set against a dark night sky.

10. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (17 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$547
includes taxes & fees
29 Sept - 30 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A bedroom with a bed, curtains, a bedside table, and a lamp.

11. Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (17 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is AU$641
includes taxes & fees
29 Sept - 30 Sept
Townhouse with Pool Table - Renovated w/ King Bed
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

12. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is AU$467
includes taxes & fees
5 Oct - 6 Oct
Real Estate: Therapy - Lake, Laundry, Love it
A compact RV kitchen with a stove, sink, and cabinets, a dining area with a bench, and a window with a view of greenery.

13. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is AU$288
includes taxes & fees
6 Oct - 7 Oct
Cozy Camper tucked into the woods
A hotel room with a bed, a nightstand, and a window with curtains.

14. 2-Bed Suite|Nsmk|Micfridge

2-Bed Suite|Nsmk|Micfridge
Enfield
8.8 out of 10, Excellent, (5 reviews)
The price is AU$154
includes taxes & fees
29 Sept - 30 Sept
2-Bed Suite|Nsmk|Micfridge
A modern kitchen with a central island, bar stools, and a bicycle.

15. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is AU$701
includes taxes & fees
5 Oct - 6 Oct
Button's Modern Luxury Walkup Downtown Northampton
A modern kitchen with a marble island, bar stools, a stainless steel stove, and a decorative chandelier.

16. Cozy 2-bedroom apartment with movie theater.

Cozy 2-bedroom apartment with movie theater.
Agawam
9.0 out of 10, Wonderful, (2 reviews)
"cute place, a bit humid and no AC control but the movie room is cool"
United States
London R.
The price is AU$411
includes taxes & fees
6 Oct - 7 Oct
Cozy 2-bedroom apartment with movie theater.
A living room with two brown leather sofas, a glass coffee table, a white rug, a ceiling fan, and a door with curtains.

17. Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
8.6 out of 10, Excellent, (21 reviews)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
The price is AU$525
includes taxes & fees
29 Sept - 30 Sept
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
A modern living room with a sofa, a coffee table, and a red patterned rug.

18. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (48 reviews)
"It was nice stay!"
United States
Lorrie
The price is AU$487
includes taxes & fees
1 Oct - 2 Oct
Cozy & Spacious Entire Home in Springfield
A bedroom with a bed, dresser, and floor lamp.

19. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths
Six Corners
The price is AU$357
includes taxes & fees
29 Sept - 30 Sept
Cozy 2-Bedroom Springfield Home 1.5 Baths
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

20. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (52 reviews)
"Great lake house in the beautiful Berkshires. House looked just like the online pics. Kitchen fully stocked with everything you would need. Lake view & backyard were amazing! Lots of fun using kayaks & canoes."
United States
Rose Angela M.
The price is AU$782
includes taxes & fees
23 Oct - 24 Oct
Cozy Cottage-Sunset On The Lake
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.
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Top Montgomery Hotel Reviews

Hotel Northampton

Hotel Northampton

8/10 Good
"The staff was excellent; very professional, pleasant and competent. The on-site parking was so convenient! The hotel shows its age a little bit—the refrigerator in my room wasn’t working, and one of the ice machines was broken—but everything was very clean and comfortable. The on-site restaurant was convenient and good. Will definitely stay here again."
Elisabeth 2-night trip
Posted 2 hours ago
Hotel Northampton

Find out more about Montgomery

Everything you need to know about Montgomery holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montgomery holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Montgomery holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montgomery. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montgomery holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montgomery holiday rentals we have selected for you start as low as AU$122 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Montgomery rentals

At Expedia, we put the best Montgomery holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Montgomery rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montgomery holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montgomery. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental 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 are some of the best holiday rentals that Montgomery has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Montgomery is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay.

What can I see and do in Montgomery?

Westfield River and Lizzie Mountain are a couple of lovely local spots to get outside and enjoy nature. Stephen Smith and Montgomery Town Hall are other places to visit while you're in town.

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 offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.