Montgomery Holiday Rentals

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Holiday Rentals in Montgomery

Our top choices for Montgomery holiday rentals

Tiny Home with AC and WiFi in lovely Ludlow

9.0 out of 10, Wonderful, (6)
The price is NZ$255
includes taxes & fees
15 Oct - 16 Oct
Tiny Home with AC and WiFi in lovely Ludlow

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (223)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

9.2 out of 10, Wonderful, (14)
"Great property! Thank you for a wonderful stay."
The price is NZ$583
includes taxes & fees
6 Oct - 7 Oct
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

9.8 out of 10, Exceptional, (36)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
The price is NZ$519
includes taxes & fees
30 Sept - 1 Oct
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (200)
"The property was beautiful and well maintained.The home where we stayed was perfect and cozy."
The Clearing - Quiet - Close To Nature

Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

10.0 out of 10, Exceptional, (23)
"This beautiful home was perfect for our short stay in Western Massachusetts. Everything was just lovely, clean, comfortable, quiet. Great hosts and so kind and accommodating to our needs. Thank you so much. We will definitely look to stay here again for future family visits. "
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

9.0 out of 10, Wonderful, (25)
"Check in was easy. This met all of our needs. "
The price is NZ$1,170
includes taxes & fees
1 Oct - 2 Oct
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

3-bedroom house in perfect Springfield with WiFi, AC

2.0 star property
9.2 out of 10, Wonderful, (5)
"Every question we had was quickly answered. The house was comfortable for us. Only a small hiccup in getting the door to lock when we left."
3-bedroom house in perfect Springfield with WiFi, AC

Peace and quiet on the lake

9.6 out of 10, Exceptional, (222)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake

Charming Chicopee Getaway

10.0 out of 10, Exceptional, (1)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
The price is NZ$463
includes taxes & fees
8 Oct - 9 Oct
Charming Chicopee Getaway

Newly Beautiful renovated first floor apartment getaway

8.0 out of 10, Very good, (2)
"We had an amazing time. This property was easy to find and very close to aloy of restaurants and shops! We had amazing chinese food! The apartment felt very homey. I love that it wasnt echo-y like past places I have stayed! I met Rose, the host, and she was super nice. She was very responsive and explained everything I needed to know before I arrived at the property. Also she lives near by and can address any problems or concerns you may have. The photography on the walls were gorgeous, the...
The price is NZ$571
includes taxes & fees
2 Oct - 3 Oct
Newly Beautiful renovated first floor apartment getaway

Charming 3 bed/2 bath town home with gorgeous back yard

9.8 out of 10, Exceptional, (12)
"Clean, comfortable house exactly as described. Easy check-in and responsive host. All amenities worked well and everything we needed was provided. Would stay here again! Highly recommended if you are looking for a place to stay during AAU basketball tournaments - location was central to all the venues."
The price is NZ$1,007
includes taxes & fees
30 Sept - 1 Oct
Charming 3 bed/2 bath town home with gorgeous back yard

PICON COZY

7.4 out of 10, Good, (69)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
The price is NZ$290
includes taxes & fees
20 Oct - 21 Oct
PICON COZY

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

9.6 out of 10, Exceptional, (62)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (140)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
The price is NZ$620
includes taxes & fees
5 Oct - 6 Oct
Big farmhouse in the foothills of the Berkshires

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (17)
"Everything was clean and comfortable. It was a perfect getaway."
Amherst, Perfect Location, UMass, Smith, MHC!

Cozy Home in Holyoke with 3 bedrooms

9.6 out of 10, Exceptional, (9)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
The price is NZ$542
includes taxes & fees
5 Oct - 6 Oct
Cozy Home in Holyoke with 3 bedrooms

Newly Renovated 4 Bedroom House

10.0 out of 10, Exceptional, (2)
"The house was perfect for a weekend wedding trip. "
Newly Renovated 4 Bedroom House

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.6 out of 10, Exceptional, (37)
"We had a lovely time. Peaceful and cozy house, great private hot tub"
The Meadows House @ Otis Ridge w/ 7-person hot tub

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

10.0 out of 10, Exceptional, (1)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
The price is NZ$717
includes taxes & fees
5 Oct - 6 Oct
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
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

Find out more about Montgomery

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 favorite 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 depends 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 NZ$255 per night. Entering your travel dates in the search wizard you might find 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?

Tiny Home with AC and WiFi in lovely Ludlow: This holiday home rental outside of Montgomery has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Montgomery?

Explore the area and family-friendly sights such as Six Flags New England, or get out into nature at a spot like Westfield River. Tekoa Mountain Wildlife Management Area 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.