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Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Montgomery vacation rentals

A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

1. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"The room was very clean and modern. The check-in process was easy and I had the best rest that I had in a long time. Being in the lower level with no windows provided a very quiet and dark ambiance at night. There is ample lighting throughout the unit if needed though, you can really unplug here. I would definitely stay here again"
United States
Kebreab H.
The price is AED 290
AED 940 total
includes taxes & fees
1 Oct - 2 Oct
Modern Studio Ideal for Traveling Professionals
Exterior

2. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"Closer to downtown able to"
United States
Jeremy R.
The price is AED 323
AED 1,223 total
includes taxes & fees
7 Oct - 8 Oct
Work, Play & Stay! Apt Near Holyoke Medical Center
A house with a porch, a garden with pink flowers, and a stone wall along the road.

3. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (152 reviews)
"Great location"
United States
Will G.
The price is AED 698
AED 1,223 total
includes taxes & fees
6 Oct - 7 Oct
Big farmhouse in the foothills of the Berkshires
A cozy room with two beds, large windows, and a view of a snowy landscape.

4. 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, (79 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is AED 661
AED 985 total
includes taxes & fees
5 Oct - 6 Oct
The Creation Station is a cozy place so make yourself at home.
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

5. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is AED 404
AED 953 total
includes taxes & fees
1 Oct - 2 Oct
Modern Studio Ideal for Traveling Professionals
A living room with a fireplace, a sofa, a coffee table, and a TV.

6. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (11 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is AED 621
AED 871 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 2-bedroom apartment in Chicopee
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

7. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 592
AED 1,449 total
includes taxes & fees
7 Oct - 8 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A living room with a sofa set, a coffee table, and two lamps.

8. Cozy First Floor Apartment. Located in a quiet neighborhood.

Cozy First Floor Apartment. Located in a quiet neighborhood.
Chicopee
9.6 out of 10, Exceptional, (12 reviews)
"Check in was very easy. The apartment had all the necessities in the kitchen and bathroom. Location was convenient and the neighborhood very safe/quiet."
United States
Morrris
The price is AED 621
AED 1,133 total
includes taxes & fees
1 Oct - 2 Oct
Cozy First Floor Apartment. Located in a quiet neighborhood.
A square fire pit with flames, surrounded by a grassy field and a green chair.

9. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (24 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is AED 344
AED 680 total
includes taxes & fees
5 Oct - 6 Oct
Peaceful Meadow Retreat
A hot tub with a string of lights above it, set against a dark night sky.

10. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (17 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 631
AED 1,411 total
includes taxes & fees
13 Oct - 14 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A bedroom with a bed, curtains, a bedside table, and a lamp.

11. Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (17 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is AED 807
AED 1,594 total
includes taxes & fees
7 Oct - 8 Oct
Townhouse with Pool Table - Renovated w/ King Bed
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

12. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.0 out of 10, Wonderful, (2 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is AED 320
AED 1,157 total
includes taxes & fees
5 Oct - 6 Oct
Real Estate: Therapy - Lake, Laundry, Love it
A compact RV kitchen with a stove, sink, and cabinets, a dining area with a bench, and a window with a view of greenery.

13. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is AED 585
AED 736 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Camper tucked into the woods
A hotel room with a bed, a nightstand, and a window with curtains.

14. 2-Bed Suite|Nsmk|Micfridge

2-Bed Suite|Nsmk|Micfridge
Enfield
8.8 out of 10, Excellent, (5 reviews)
The price is AED 404
AED 464 total
includes taxes & fees
1 Oct - 2 Oct
2-Bed Suite|Nsmk|Micfridge
A modern kitchen with a central island, bar stools, and a bicycle.

15. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 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 AED 897
AED 1,728 total
includes taxes & fees
5 Oct - 6 Oct
Button's Modern Luxury Walkup Downtown Northampton
A modern kitchen with a marble island, bar stools, a stainless steel stove, and a decorative chandelier.

16. Cozy 2-bedroom apartment with movie theater.

Cozy 2-bedroom apartment with movie theater.
Agawam
9.0 out of 10, Wonderful, (2 reviews)
"cute place, a bit humid and no AC control but the movie room is cool"
United States
London R.
The price is AED 658
AED 1,022 total
includes taxes & fees
6 Oct - 7 Oct
Cozy 2-bedroom apartment with movie theater.
A living room with two brown leather sofas, a glass coffee table, a white rug, a ceiling fan, and a door with curtains.

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

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
8.6 out of 10, Excellent, (21 reviews)
"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 AED 661
AED 1,446 total
includes taxes & fees
4 Oct - 5 Oct
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
A modern living room with a sofa, a coffee table, and a red patterned rug.

18. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (49 reviews)
"It was nice stay!"
United States
Lorrie
The price is AED 612
AED 1,194 total
includes taxes & fees
1 Oct - 2 Oct
Cozy & Spacious Entire Home in Springfield
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

19. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (53 reviews)
"Great lake house in the beautiful Berkshires. House looked just like the online pics. Kitchen fully stocked with everything you would need. Lake view & backyard were amazing! Lots of fun using kayaks & canoes."
United States
Rose Angela M.
Cozy Cottage-Sunset On The Lake
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

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"G"
Albert 2-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Springfield MA

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?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation home rental outside of Montgomery is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

What can I see and do in Montgomery?

Westfield River and Lizzie Mountain are a couple of lovely local spots to get outside and enjoy nature. Stephen Smith and Montgomery Town Hall 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.