Holiday Rentals in Montgomery

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Holiday Rentals in Montgomery

Tiny Home with AC and WiFi in lovely Ludlow

Ludlow
8.4 out of 10, Very good, (8)
"Good stay for an overnight in the area, location was a little tricky to find at night but once I did it was easy to get in. Had all the amenities needed for a short stay and is near the highway for quick on and off."
United States
Matthew H.
The price is €132
includes taxes & fees
6 Dec - 7 Dec
Tiny Home with AC and WiFi in lovely Ludlow

Cozy Home in Holyoke with 3 bedrooms

Holyoke
9.8 out of 10, Exceptional, (12)
"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."
United States
Eric W.
The price is €282
includes taxes & fees
7 Dec - 8 Dec
Cozy Home in Holyoke with 3 bedrooms

Peaceful Meadow Retreat

2.0 star property
Granby
10.0 out of 10, Exceptional, (16)
"The place is beautiful and very quiet and relaxing"
United States
Marian
The price is €175
includes taxes & fees
7 Dec - 8 Dec
Peaceful Meadow Retreat

The Serene Skyway Retreat

Windsor Locks
8.8 out of 10, Excellent, (11)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
The price is €239
includes taxes & fees
6 Dec - 7 Dec
The Serene Skyway Retreat

Townhouse with Pool Table - Renovated w/ King Bed

Chicopee
10.0 out of 10, Exceptional, (11)
"The townhouse was perfect for our short trip. It was located close to everything we needed. The house was as described and we would stay here again."
United States
Matt G.
The price is €337
includes taxes & fees
7 Dec - 8 Dec
Townhouse with Pool Table - Renovated w/ King Bed

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

Easthampton Ma.
10.0 out of 10, Exceptional, (72)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is €243
includes taxes & fees
8 Dec - 9 Dec
The Creation Station is a cozy place so make yourself at home.

Home in the Woods

Russell
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
United States
Travis H.
The price is €282
includes taxes & fees
5 Dec - 6 Dec
Home in the Woods

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

Boston Road
9.2 out of 10, Wonderful, (13)
"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 €281
includes taxes & fees
7 Dec - 8 Dec
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

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

Amherst
9.4 out of 10, Exceptional, (16)
"Great property! Thank you for a wonderful stay."
United States
David
The price is €377
includes taxes & fees
7 Dec - 8 Dec
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Boston Road
9.0 out of 10, Wonderful, (10)
"Great stay"
United States
Angelina O.
The price is €281
includes taxes & fees
8 Dec - 9 Dec
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Newly Beautiful renovated first floor apartment getaway

Forest Park
8.8 out of 10, Excellent, (3)
"This was a spacious 4 bedroom. Clean and smooth check in and out. Thank you for having me and my guest "
United States
Alyssa A.
The price is €299
includes taxes & fees
7 Dec - 8 Dec
Newly Beautiful renovated first floor apartment getaway

Welcome to Honey Spot!

Pine Point
9.8 out of 10, Exceptional, (27)
"Ricardo was a great!!made are stay wonderful was very helpful and went out of his way to make or stay great we had a good time place was beautiful something for everyone will definitely stay here again thank u"
United States
Marie A.
The price is €262
includes taxes & fees
31 Dec - 1 Jan 2026
Welcome to Honey Spot!

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Windsor Locks
10.0 out of 10, Exceptional, (2)
"We loved this space for our short stay. The rooms and space were cozy with a fun theme. Everything was clean and check in/out was easy. The host was responsive and helpful. We would stay here again"
United States
Amanda W.
The price is €391
includes taxes & fees
7 Dec - 8 Dec
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €332
includes taxes & fees
8 Dec - 9 Dec
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Granby
9.4 out of 10, Exceptional, (20)
"Great overnight stay! "
United States
Carrie M.
The price is €237
includes taxes & fees
6 Dec - 7 Dec
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is €345
includes taxes & fees
15 Dec - 16 Dec
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

Sixteen Acres
9.0 out of 10, Wonderful, (4)
"Overall great spot and very clean. Lots of space to accommodate large groups, and the listing is transparent. The only reason I took off 1 star is all of the beds were very stiff and uncomfortable, which unfortunately would keep me from rebooking. However, if that doesn’t bother you, this place is a great little spot to stay the night if you’re in the area. "
United States
Lauren H.
The price is €316
includes taxes & fees
10 Dec - 11 Dec
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

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

Enfield
10.0 out of 10, Exceptional, (2)
"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."
United States
Logan M.
The price is €370
includes taxes & fees
31 Dec - 1 Jan 2026
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

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

Forest Park
9.8 out of 10, Exceptional, (36)
"His home was great. It had everything our group needed and was as advertised. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
The price is €270
includes taxes & fees
5 Dec - 6 Dec
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Charming Chicopee Getaway

Chicopee
7.4 out of 10, Good, (3)
"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. "
United States
Tamara S.
The price is €269
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Chicopee Getaway
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

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, apart-hotels, 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 €132 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?

Peace and quiet on the lake: This holiday home rental outside of Montgomery is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

What can I see and do in Montgomery?

Explore the area and family-friendly sights such as International Volleyball Hall of Fame, or get out into nature at a spot like Westfield River. Montgomery Town Hall and Grace Hall Memorial Library 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.