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Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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, (149 reviews)
"Great location"
United States
Will G.
$314 nightly
The price is $332
Sep 14 - Sep 15
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Apartment (0 Bedroom) | Interior

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

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
$242 nightly
The price is $271
Sep 2 - Sep 3
Total with taxes and fees
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Desk, iron/ironing board, travel crib, WiFi

3. 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
$252 nightly
The price is $281
Sep 14 - Sep 15
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
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
$249 nightly
The price is $278
Sep 2 - Sep 3
Total with taxes and fees
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.
$301 nightly
The price is $336
Sep 29 - Sep 30
Total with taxes and fees
Work, Play & Stay! Apt Near Holyoke Medical Center
Coffee/tea maker, fridge, microwave, oven

6. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (22 reviews)
"Fantastic stay in Holyoke. House is close to town, well outfitted, and super clean. Easy check in process and great experience all around. "
United States
Grant J.
$355 nightly
The price is $397
Sep 7 - Sep 8
Total with taxes and fees
Cozy Home in Holyoke with 3 bedrooms
Living area

7. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (9 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
$227 nightly
The price is $258
Sep 29 - Sep 30
Total with taxes and fees
Cozy 2-bedroom apartment in Chicopee
Flat-screen TV, books

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
$273 nightly
The price is $310
Sep 13 - Sep 14
Total with taxes and fees
Cozy First Floor Apartment. Located in a quiet neighborhood.
Interior

9. 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.
$259 nightly
The price is $289
Sep 13 - Sep 14
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
3 bedrooms, desk, iron/ironing board, travel crib

10. 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.
$433 nightly
The price is $492
Sep 15 - Sep 16
Total with taxes and fees
Townhouse with Pool Table - Renovated w/ King Bed
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.
$355 nightly
The price is $397
Sep 7 - Sep 8
Total with taxes and fees
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.
$338 nightly
The price is $377
Sep 9 - Sep 10
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Interior

13. 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.
$361 nightly
The price is $381
Sep 13 - Sep 14
Total with taxes and fees
Linny's - Private Dock - Lake Access - Firepit
Coffee/tea maker, fridge, microwave, oven

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.
$273 nightly
The price is $305
Sep 14 - Sep 15
Total with taxes and fees
Cozy 2-bedroom apartment with movie theater.
TV

15. Charming Chicopee Getaway

Charming Chicopee Getaway
Chicopee
7.6 out of 10, Good, (4 reviews)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
United States
Tamara S.
$209 nightly
The price is $244
Sep 14 - Sep 15
Total with taxes and fees
Charming Chicopee Getaway
Interior

16. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (6 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
$450 nightly
The price is $503
Sep 7 - Sep 8
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
Property grounds

17. 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
$392 nightly
The price is $414
Sep 2 - Sep 3
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
Apartment (3 Bedrooms) | Front of property

18. Steps to Holyoke Medical Center! Remote-work Hub

Steps to Holyoke Medical Center! Remote-work Hub
3.0 star property
Holyoke
$494 nightly
The price is $552
Sep 8 - Sep 9
Total with taxes and fees
Steps to Holyoke Medical Center! Remote-work Hub
Smart TV

19. 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, (19 reviews)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
$349 nightly
The price is $396
Sep 2 - Sep 3
Total with taxes and fees
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Lobby

20. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Enfield
$75 nightly
The price is $86
Sep 2 - Sep 3
Total with taxes and fees
1 King Bed | Non-Smoking
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

Hotel Northampton

Hotel Northampton

8/10 Good
"Awesome location, lovely property for downtown, great parking. Spacious rooms with comfy beds and bedding. Staff at restaurant and bar stellar! Cocktails spot on...Sadly food not so much."
willa 2-night trip
Posted less than an hour ago
Hotel Northampton

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 $244 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.

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. 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.