Search Vacation Homes in Montgomery

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Dec 19 - Dec 21
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Dec 26 - Dec 28
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Jan 9 - Jan 11
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Feb 6 - Feb 8

Our top choices for Montgomery vacation homes

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 13 - Dec 14
Total with taxes and fees
Tiny Home with AC and WiFi in lovely Ludlow
Dining
The Serene Skyway Retreat

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (12)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
$256 nightly
The price is $272
Dec 21 - Dec 22
Total with taxes and fees
The Serene Skyway Retreat
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 13 - Dec 14
Total with taxes and fees
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
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 13 - Dec 14
Total with taxes and fees
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Terrace/patio
Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms

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.
$288 nightly
The price is $322
Dec 14 - Dec 15
Total with taxes and fees
Cozy Home in Holyoke with 3 bedrooms
Fridge, microwave, oven, stovetop
Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed

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.
$337 nightly
The price is $382
Dec 14 - Dec 15
Total with taxes and fees
Townhouse with Pool Table - Renovated w/ King Bed
Private kitchen
Home in the Woods

Home in the Woods

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.
Home in the Woods
Property grounds
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

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
East Granby
8.6 out of 10, Excellent, (4)
"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.
$367 nightly
The price is $417
Dec 15 - Dec 16
Total with taxes and fees
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Property grounds
The Creation Station is a cozy place so make yourself at home.

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, (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.
$248 nightly
The price is $277
Dec 22 - Dec 23
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
Fridge, microwave, stovetop, dishwasher
Newly Renovated 4 Bedroom House

Newly Renovated 4 Bedroom House

Newly Renovated 4 Bedroom House
Enfield
10.0 out of 10, Exceptional, (4)
"The house was perfect for a weekend wedding trip. "
United States
Liane V.
$421 nightly
The price is $443
Jan 4 - Jan 5, 2026
Total with taxes and fees
Newly Renovated 4 Bedroom House
Fridge, microwave, oven, stovetop
Newly Beautiful renovated first floor apartment getaway

Newly Beautiful renovated first floor apartment getaway

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.
$301 nightly
The price is $341
Dec 14 - Dec 15
Total with taxes and fees
Newly Beautiful renovated first floor apartment getaway
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!
Private kitchen
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

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)
"Mini family vacation. The property was pleasant and convenient to the Museums and Zoo.This is not specific to this stay, but I wish the fees would be available prior to the booking/ payment process. We had to stop the booking of a different property for this trip when the hidden fees more than doubled the cost of the rental."
United States
Michael P.
$318 nightly
The price is $361
Dec 15 - Dec 16
Total with taxes and fees
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Fridge, microwave, oven, stovetop
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

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

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.
$253 nightly
The price is $267
Dec 14 - Dec 15
Total with taxes and fees
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
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.
$267 nightly
The price is $303
Dec 13 - Dec 14
Total with taxes and fees
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
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
Fridge, microwave, oven, stovetop
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

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

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.
$391 nightly
The price is $443
Dec 14 - Dec 15
Total with taxes and fees
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
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
Private kitchen
Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home
2.0 star property
Chicopee
$298 nightly
The price is $338
Dec 14 - Dec 15
Total with taxes and fees
Welcoming 3-bedroom house- Gardner home
Dining
Luxury Retreat inAmherst

Luxury Retreat inAmherst

Luxury Retreat inAmherst
Amherst
10.0 out of 10, Exceptional, (1)
"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
$750 nightly
The price is $838
Dec 15 - Dec 16
Total with taxes and fees
Luxury Retreat inAmherst
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 5 hours ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Find out more about Montgomery

Montgomery Vacation Homes information

Number of reviews
291
Accommodation
167 Vacation Homes
Lowest Price
$150
Highest Price
$838

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