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Montgomery Vacation Rentals

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

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, (150 reviews)
"Great location"
United States
Will G.
$312 nightly
The price is $330
Sep 14 - Sep 15
Total with taxes and fees
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, (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
$239 nightly
The price is $267
Sep 14 - Sep 15
Total with taxes and fees
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. Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
$213 nightly
The price is $238
Sep 21 - Sep 22
Total with taxes and fees
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

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
$217 nightly
The price is $242
Sep 21 - Sep 22
Total with taxes and fees
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

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.
$291 nightly
The price is $325
Sep 29 - Sep 30
Total with taxes and fees
Work, Play & Stay! Apt Near Holyoke Medical Center
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, (10 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
Oct 6 - Oct 7
Total with taxes and fees
Cozy 2-bedroom apartment in Chicopee
A bedroom with a bed, curtains, a bedside table, and a lamp.

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.
$435 nightly
The price is $494
Sep 28 - Sep 29
Total with taxes and fees
Townhouse with Pool Table - Renovated w/ King Bed
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
$270 nightly
The price is $306
Sep 14 - Sep 15
Total with taxes and fees
Cozy First Floor Apartment. Located in a quiet neighborhood.
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
$427 nightly
The price is $477
Sep 14 - Sep 15
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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.
$260 nightly
The price is $290
Sep 16 - Sep 17
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
A hot tub with a string of lights above it, set against a dark night sky.

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.
$366 nightly
The price is $409
Sep 15 - Sep 16
Total with taxes and fees
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.

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.
$335 nightly
The price is $374
Sep 14 - Sep 15
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A bedroom with a bed, a window, a shelf with books, and a mirror.

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

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
$306 nightly
The price is $341
Sep 14 - Sep 15
Total with taxes and fees
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

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
$384 nightly
The price is $406
Sep 14 - Sep 15
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
A modern kitchen with a marble island, bar stools, a stainless steel stove, and a decorative chandelier.

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.
$270 nightly
The price is $302
Sep 14 - Sep 15
Total with taxes and fees
Cozy 2-bedroom apartment with movie theater.
A two-story house with a porch, a large tree in front, and a mailbox.

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.
$615 nightly
The price is $698
Sep 14 - Sep 15
Total with taxes and fees
Modern Victorian 3BR 2BA Apt with Parking
A spacious kitchen with a large island, wooden beams, and pendant lighting.

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.
$390 nightly
The price is $412
Oct 14 - Oct 15
Total with taxes and fees
Linny's - Private Dock - Lake Access - Firepit
A garden area with potted plants, a wooden fence, and outdoor furniture.

18. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
$199 nightly
The price is $222
Sep 14 - Sep 15
Total with taxes and fees
Cozy Camper tucked into the woods
A square fire pit with flames, surrounded by a grassy field and a green chair.

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.
$167 nightly
The price is $190
Oct 5 - Oct 6
Total with taxes and fees
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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

8/10 Good
"The bed was a little lumpy"
Christine 1-night trip
Posted less than an hour ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

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 $330 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?

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.