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Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Montgomery vacation rentals

Property grounds

1. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (150 reviews)
"Great location"
United States
Will G.
The price is ￥26,267
￥50,657 total
includes taxes & fees
Sep 27 - Sep 28
Big farmhouse in the foothills of the Berkshires
Room

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, (77 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 ￥27,650
￥41,180 total
includes taxes & fees
Sep 14 - Sep 15
The Creation Station is a cozy place so make yourself at home.
Apartment (0 Bedroom) | Interior

3. Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is ￥13,979
￥36,604 total
includes taxes & fees
Sep 21 - Sep 22
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Exterior

4. Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"The studio was clean, new and modern. There are no windows so it was dark and quiet to sleep. "
United States
Michelle
The price is ￥9,524
￥37,234 total
includes taxes & fees
Sep 21 - Sep 22
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Exterior

5. 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 ￥10,445
￥49,930 total
includes taxes & fees
Sep 29 - Sep 30
Work, Play & Stay! Apt Near Holyoke Medical Center
Living area

6. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (10 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is ￥27,803
￥39,560 total
includes taxes & fees
Oct 6 - Oct 7
Cozy 2-bedroom apartment in Chicopee
Room

7. 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 ￥41,167
￥80,164 total
includes taxes & fees
Oct 7 - Oct 8
Townhouse with Pool Table - Renovated w/ King Bed
Living area

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 ￥25,960
￥47,052 total
includes taxes & fees
Sep 14 - Sep 15
Cozy First Floor Apartment. Located in a quiet neighborhood.
Interior

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 ￥37,493
￥76,882 total
includes taxes & fees
Sep 21 - Sep 22
Button's Modern Luxury Walkup Downtown Northampton
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very Good, (1 review)
"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 ￥7,988
￥44,612 total
includes taxes & fees
Sep 16 - Sep 17
Real Estate: Therapy - Lake, Laundry, Love it
Outdoor spa tub

11. 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, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥26,544
￥62,765 total
includes taxes & fees
Sep 15 - Sep 16
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

12. 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 ￥22,396
￥57,445 total
includes taxes & fees
Sep 14 - Sep 15
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Room

13. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is ￥33,733
￥52,437 total
includes taxes & fees
Sep 14 - Sep 15
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Property grounds

14. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveler
The price is ￥38,986
￥62,803 total
includes taxes & fees
Sep 14 - Sep 15
Charming, updated 3 bedroom farmhouse farm stay.
Private kitchen

15. 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 ￥29,032
￥46,327 total
includes taxes & fees
Sep 14 - Sep 15
Cozy 2-bedroom apartment with movie theater.
Exterior detail

16. Modern Victorian 3BR 2BA Apt with Parking

Modern Victorian 3BR 2BA Apt with Parking
McKnight
10.0 out of 10, Exceptional, (2 reviews)
"Great house. Very spacious. Perfect for friends gathering for a local event. "
United States
Marcy Z.
The price is ￥58,372
￥107,179 total
includes taxes & fees
Sep 14 - Sep 15
Modern Victorian 3BR 2BA Apt with Parking
Interior

17. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is ￥33,333
￥63,322 total
includes taxes & fees
Oct 14 - Oct 15
Linny's - Private Dock - Lake Access - Firepit
Outdoor dining

18. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
The price is ￥26,682
￥34,094 total
includes taxes & fees
Sep 14 - Sep 15
Cozy Camper tucked into the woods
Property grounds

19. 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 ￥15,975
￥29,354 total
includes taxes & fees
Oct 5 - Oct 6
Peaceful Meadow Retreat
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 Hartford - Bradley Airport

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

8/10 Good
"For the price margin and star rating - I was very pleased with my stay. The bed was very comfortable. The room clean and with decent furniture. The bathroom had a updated sliding glass door for shower. I decided to eat breakfast next door because of the rating of the diner, but they did offer breakfast as well. I would stay there again."
Craig 1-night trip
Posted 4 hours ago
La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

Find out more about Montgomery

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

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?

Lizzie Mountain and Westfield River are a couple of lovely local spots to get outside and enjoy nature. 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.