Montgomery Vacation Rentals

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In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Montgomery vacation rentals

Interior
Peace and quiet on the lake

Peace and quiet on the lake

Peace and quiet on the lake
Sherwood Forest
9.6 out of 10, Exceptional, (230)
"Great communication, comfortable home, love the location"
United States
Susan C.
Peace and quiet on the lake
Exterior detail
Elm Suite with a Private Bathroom in front of Smith College Quadrangle

Elm Suite with a Private Bathroom in front of Smith College Quadrangle

Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Northampton
9.8 out of 10, Exceptional, (23)
"Gorgeous building, clean and cozy spot to stay. "
United States
Grace
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Fridge, microwave, oven, stovetop
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

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

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.
$280 nightly
The price is $318
Dec 14 - Dec 15
Total with taxes and fees
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Outdoor pool
The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature
Cummington
10.0 out of 10, Exceptional, (211)
"This was the perfect little home for my husband and I to stay for a few days while we visited the area. Loved it."
Canada
Andrea F.
The Clearing - Quiet - Close To Nature
Full-size fridge, microwave, oven, dishwasher
Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
$580 nightly
The price is $638
Dec 18 - Dec 19
Total with taxes and fees
Newly Renovated 2 floor Getaway
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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
9.6 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.
$349 nightly
The price is $390
Dec 15 - Dec 16
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Property grounds
Experience Three Sisters Sanctuary in Goshen, MA

Experience Three Sisters Sanctuary in Goshen, MA

Experience Three Sisters Sanctuary in Goshen, MA
2.0 star property
Goshen
10.0 out of 10, Exceptional, (2)
"We had such a great time staying here as always. "
United States
David F.
Experience Three Sisters Sanctuary in Goshen, MA
HOMEY HOMEY

HOMEY HOMEY

HOMEY HOMEY
Sixteen Acres
2.8 out of 10, (5)
"We did not even stay. The upstairs has access to the basement door so I did not at all feel comfortable. And there is a terrible mildew smell. "
United States
Erin N.
$147 nightly
The price is $167
Dec 14 - Dec 15
Total with taxes and fees
HOMEY HOMEY
Fridge, microwave, oven, stovetop
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!

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Amherst
9.4 out of 10, Exceptional, (17)
"Great property! Thank you for a wonderful stay."
United States
David
$375 nightly
The price is $419
Dec 15 - Dec 16
Total with taxes and fees
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Fireplace, books
3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest

3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest

3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest
Cummington
9.6 out of 10, Exceptional, (40)
"My friends and I had the most beautiful rainy weekend here to celebrate my 40th birthday. The spot was perfect for the 5 of us and the river was such a wonderful bonus to our peaceful trip!"
United States
Sarah R.
3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest
Exterior
Tiny Home with AC and WiFi in lovely Ludlow

Tiny Home with AC and WiFi in lovely Ludlow

Tiny Home with AC and WiFi in lovely Ludlow
Ludlow
8.4 out of 10, Very Good, (9)
"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.
$134 nightly
The price is $150
Dec 14 - Dec 15
Total with taxes and fees
Tiny Home with AC and WiFi in lovely Ludlow
Fridge, microwave, oven, stovetop
Linny’s Lake House with dock

Linny’s Lake House with dock

Linny’s Lake House with dock
West Suffield
9.8 out of 10, Exceptional, (27)
"We had an amazing time really nice neighborhood. We'll definitely be back next year."
United States
Aimee W.
Linny’s Lake House with dock
Smart TV
PICON COZY

PICON COZY

PICON COZY
Sixteen Acres
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. "
United States
Linda W.
$151 nightly
The price is $171
Dec 23 - Dec 24
Total with taxes and fees
PICON COZY
Fridge, microwave, oven, stovetop
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment 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)
"This home was great. It had everything our large group needed and was as advertised. The owner was great to communicate with. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
$462 nightly
The price is $524
Dec 14 - Dec 15
Total with taxes and fees
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. 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.
$335 nightly
The price is $374
Dec 15 - Dec 16
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Microwave, oven, stovetop
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

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

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.
$372 nightly
The price is $421
Dec 31 - Jan 1, 2026
Total with taxes and fees
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
TV
3-bedroom house in perfect Springfield with WiFi, AC

3-bedroom house in perfect Springfield with WiFi, AC

3-bedroom house in perfect Springfield with WiFi, AC
2.0 star property
Pine Point
9.6 out of 10, Exceptional, (7)
"The whole experience was great. The host was very nice and the place is comfy and enjoyable to stay at. Highly recommend. "
United States
Joel K.
3-bedroom house in perfect Springfield with WiFi, AC
Smart TV, fireplace, video games, books
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!

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.
$266 nightly
The price is $302
Dec 14 - Dec 15
Total with taxes and fees
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Dining
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

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

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.
$283 nightly
The price is $321
Dec 14 - Dec 15
Total with taxes and fees
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale
9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

10/10 Excellent
"Bookee the king suite. More than enough room for 2 people. Has a full fridge and kitchenette wwgich as nice for light cooking. Close to the airport. Most of the staff was friendly, had a dlightissue with one of the desk staff during check in but the other staff corrected it. Cleqn room, clean building, comfortable bed. issue with "
dezaree 3-night trip
Posted 19 hours ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Find out more about Montgomery

Everything you need to know about Montgomery vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montgomery vacation 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 low season months. For more hustle and bustle, you may prefer to visit Montgomery in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montgomery rentals

At Expedia, we put the best Montgomery vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.