Montgomery Vacation Rentals

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Our top choices for Montgomery vacation rentals

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (14 reviews)
"Very neat and clean. Decorated for Fall, which was nice. All amenities made for a really nice time."
United States
Stacy G.
The price is CA $177
CA $451 total
includes taxes & fees
Feb 19 - Feb 20
Cozy Home in Holyoke with 3 bedrooms

Tiny Home with AC and WiFi in lovely Ludlow

Tiny Home with AC and WiFi in lovely Ludlow
Ludlow
8.2 out of 10, Very good, (10 reviews)
"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 CA $108
CA $204 total
includes taxes & fees
Feb 19 - Feb 20
Tiny Home with AC and WiFi in lovely Ludlow

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (12 reviews)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
The price is CA $121
CA $397 total
includes taxes & fees
Mar 2 - Mar 3
The Serene Skyway Retreat

Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (12 reviews)
"Perfect stay for a family. Enjoyed the pool table. Beds were comfortable. Showers were perfect. Beautifully decorated. We felt right at home. Would definitely stay again. "
United States
Tonya Z.
The price is CA $245
CA $528 total
includes taxes & fees
Feb 20 - Feb 21
Townhouse with Pool Table - Renovated w/ King Bed

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

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Sixteen Acres
8.8 out of 10, Excellent, (5 reviews)
"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 CA $282
CA $497 total
includes taxes & fees
Feb 19 - Feb 20
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

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

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Amherst
9.2 out of 10, Wonderful, (19 reviews)
"Great property! Thank you for a wonderful stay."
United States
David
The price is CA $306
CA $579 total
includes taxes & fees
Feb 20 - Feb 21
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Cozy 2-bedroom apartment with movie theater.

Cozy 2-bedroom apartment with movie theater.
Agawam
The price is CA $244
CA $398 total
includes taxes & fees
Feb 20 - Feb 21
Cozy 2-bedroom apartment with movie theater.

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (17 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is CA $128
CA $252 total
includes taxes & fees
Feb 23 - Feb 24
Peaceful Meadow Retreat

Beautiful 2-bedroom cottage on Robert Frost Trail

Beautiful 2-bedroom cottage on Robert Frost Trail
Amherst
The price is CA $218
CA $364 total
includes taxes & fees
Feb 22 - Feb 23
Beautiful 2-bedroom cottage on Robert Frost Trail

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is CA $245
CA $468 total
includes taxes & fees
Mar 15 - Mar 16
Big farmhouse in the foothills of the Berkshires

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

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Forest Park
9.6 out of 10, Exceptional, (37 reviews)
"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 CA $184
CA $415 total
includes taxes & fees
Feb 23 - Feb 24
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
East Granby
8.6 out of 10, Excellent, (4 reviews)
"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"
United States
Sgt W.
The price is CA $296
CA $733 total
includes taxes & fees
Feb 19 - Feb 20
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

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

Charming 3 bed/2 bath town home with gorgeous back yard
Forest Park
9.8 out of 10, Exceptional, (13 reviews)
"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."
United States
Barbara W.
The price is CA $779
CA $1,011 total
includes taxes & fees
Feb 19 - Feb 20
Charming 3 bed/2 bath town home with gorgeous back yard

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.8 out of 10, Exceptional, (11 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is CA $218
CA $538 total
includes taxes & fees
Feb 23 - Feb 24
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Newly Beautiful renovated first floor apartment getaway

Newly Beautiful renovated first floor apartment getaway
Forest Park
8.8 out of 10, Excellent, (3 reviews)
"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 CA $227
CA $434 total
includes taxes & fees
Mar 1 - Mar 2
Newly Beautiful renovated first floor apartment getaway

Luxury Retreat inAmherst

Luxury Retreat inAmherst
Amherst
10.0 out of 10, Exceptional, (1 review)
"Very helpful and easy communication. Very clean and nice place. We were very busy and only really were at the place to sleep but it is quiet and perfect for a restful stay."
United States
Robert
The price is CA $736
CA $1,158 total
includes taxes & fees
Feb 20 - Feb 21
Luxury Retreat inAmherst

Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (2 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 CA $449
CA $830 total
includes taxes & fees
Feb 23 - Feb 24
Button's Modern Luxury Walkup Downtown Northampton

Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home
Chicopee
10.0 out of 10, Exceptional, (1 review)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
The price is CA $205
CA $524 total
includes taxes & fees
Feb 22 - Feb 23
Welcoming 3-bedroom house- Gardner home

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

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Forest Park
9.0 out of 10, Wonderful, (28 reviews)
"Great. Placeto stay"
United States
Anonymous traveller
The price is CA $392
CA $716 total
includes taxes & fees
Feb 21 - Feb 22
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Montgomery. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Montgomery?

Yes, you can find vacation rentals near popular sights in Montgomery, or you can go with a secluded option if you're looking for relaxation.

What's the top vacation rental in Montgomery?

Peace and quiet on the lake: This vacation home rental outside of Montgomery is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection 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 Holyoke Heritage State Park, 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 vacation rentals like in Montgomery?

Vacation rentals are private accommodations you can reserve for several days or more in Montgomery. Vacation rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for small groups.