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Montgomery Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Montgomery holiday rentals

A house with a porch, a garden with pink flowers, and a stone wall along the road.

1. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (153 reviews)
"Great place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
United States
Dale B.
The price is HK$1,538
HK$2,820 total
includes taxes & fees
22 Oct - 23 Oct
Big farmhouse in the foothills of the Berkshires
A cozy room with two beds, large windows, and a view of a snowy landscape.

2. 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 HK$1,413
HK$2,174 total
includes taxes & fees
2 Nov - 3 Nov
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."

3. 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 HK$518
HK$1,937 total
includes taxes & fees
14 Oct - 15 Oct
Modern Studio Ideal for Traveling Professionals
Exterior

4. 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 HK$691
HK$2,752 total
includes taxes & fees
14 Oct - 15 Oct
Work, Play & Stay! Apt Near Holyoke Medical Center
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 HK$746
HK$1,905 total
includes taxes & fees
14 Oct - 15 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, (13 reviews)
The price is HK$1,279
HK$1,852 total
includes taxes & fees
2 Nov - 3 Nov
Cozy 2-bedroom apartment in Chicopee
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

7. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (55 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is HK$2,001
HK$4,611 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Cottage-Sunset On The Lake
A bedroom with a bed, curtains, a bedside table, and a lamp.

8. 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 HK$1,821
HK$3,659 total
includes taxes & fees
10 Nov - 11 Nov
Townhouse with Pool Table - Renovated w/ King Bed
A modern kitchen with a central island, bar stools, and a bicycle.

9. 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 HK$1,915
HK$3,928 total
includes taxes & fees
20 Oct - 21 Oct
Button's Modern Luxury Walkup Downtown Northampton
A living room with a sofa set, a coffee table, and two lamps.

10. 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 HK$1,483
HK$2,546 total
includes taxes & fees
27 Oct - 28 Oct
Cozy First Floor Apartment. Located in a quiet neighborhood.
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

11. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (43 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is HK$2,119
HK$3,484 total
includes taxes & fees
14 Oct - 15 Oct
Charming, updated 3 bedroom farmhouse farm stay.
A hot tub with a string of lights above it, set against a dark night sky.

12. 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, (18 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,397
HK$3,261 total
includes taxes & fees
28 Oct - 29 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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.

13. 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 HK$1,144
HK$2,944 total
includes taxes & fees
14 Oct - 15 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern kitchen with a marble island, bar stools, a stainless steel stove, and a decorative chandelier.

14. 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 HK$1,766
HK$2,717 total
includes taxes & fees
14 Oct - 15 Oct
Cozy 2-bedroom apartment with movie theater.
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 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 HK$549
HK$2,454 total
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

16. 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 HK$1,257
HK$1,580 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Camper tucked into the woods
A square fire pit with flames, surrounded by a grassy field and a green chair.

17. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (24 reviews)
Peaceful Meadow Retreat
A bedroom with a bed, dresser, mirror, and a cabinet with glass doors.

18. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (1 review)
"Great space. Great location."
United States
Mike S.
The price is HK$2,943
HK$5,479 total
includes taxes & fees
27 Oct - 28 Oct
Penthouse overlooking downtown Amherst!
A dining area with a round table, four chairs, and a kitchen in the background.

19. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths
Six Corners
The price is HK$1,405
HK$1,951 total
includes taxes & fees
14 Oct - 15 Oct
Cozy 2-Bedroom Springfield Home 1.5 Baths
A two-story house with a porch, a large tree in front, and a mailbox.

20. Modern Victorian 3BR 2BA Apt with Parking

Modern Victorian 3BR 2BA Apt with Parking
McKnight
10.0 out of 10, Exceptional, (3 reviews)
"This is a beautiful old Victorian home. Very well maintained and very well appointed. The hosts are attentive and respond to questions promptly. The house was well stocked with all essentials Highly recommended."
United States
Brandi S.
The price is HK$3,139
HK$5,716 total
includes taxes & fees
14 Oct - 15 Oct
Modern Victorian 3BR 2BA Apt with Parking
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
"It was a great place close to the airport."
Rebecca 1-night trip
Posted 2 hours ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Find out more about Montgomery

Search for holiday rentals in Montgomery on Expedia! You can easily find your home rentals, villas, holiday apartments in Montgomery using one of the methods below:

  • View our selection of featured holiday rentals in Montgomery
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  • Enter your travel dates to view the best deals on holiday rentals in Montgomery while they last

Look no further and take a look at our great range of rental properties in Montgomery!

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?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday 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 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.