Montgomery Holiday Rentals

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Holiday Rentals in Montgomery

Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, (34)
"Nice place!"
The price is AU$391
per night
10 June - 11 June
Cozy apartment located in quiet Williamsburg
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
PICON COZY
8.0 out of 10, Very good, (43)
"Fidelis demonstrated exceptional professionalism throughout our interaction. He was remarkably accommodating, consistently honest, and promptly addressed any inquiries I had, usually within minutes. On the rare occasion that he couldn't respond immediately, he took the time to provide an explanation and offer his apologies. Recently, my son relocated to this area for work, and thanks to Fidelis, I can now rest assured that my 24-year-old son, who has yet to experience living on his own, is safe...
The price is AU$262
per night
10 June - 11 June
PICON COZY
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Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (52)
"Wonderful place to stay, had a great time lots of instruments to try, had lots of space to spread out and hangout, the hot tub was very nice and clean. Overall had a fantastic stay the lighted walkway is amazing! All the amenities available where also great, Jon was a great host and we had a great time speaking with him!"
The price is AU$367
per night
10 June - 11 June
The Creation Station is a cozy place so make yourself at home.
Peace and quiet on the lake
9.6 out of 10, Exceptional, (185)
"It was exactly as stated... Peace and quiet on the lake! With all the amenities, Beautiful backyard, Fire pit, Kayaks and canoes, Beautiful backdeck. Just an all around nice place to stay and relax."
Peace and quiet on the lake
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
10.0 out of 10, Exceptional, (2)
"It was wonderful! Enough room for everyone and everything was cozy and working. Appreciate the stay!"
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, (7)
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
Welcome to Honey Spot!
10.0 out of 10, Exceptional, (24)
"We loved this property! Had everything we needed and we didn't have time to use or enjoy everything. The beds were SO COMFY!!! Loved having 2 bathrooms also. Great communication with the host! We would love to come back!"
The price is AU$467
per night
10 June - 11 June
Welcome to Honey Spot!
Massachusetts Vacation Rental w/ Deck
9.4 out of 10, Exceptional, (10)
"Great property. Easy check in and communication with the owner."
Massachusetts Vacation Rental w/ Deck
Beautiful retreat to the woods to enjoy the winter season.
10.0 out of 10, Exceptional, (31)
"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."
Beautiful retreat to the woods to enjoy the winter season.
Thomas's Cozy Duplex - Centrally Located
8.0 out of 10, Very good, (5)
"Enjoyed our weekend. Check in was easy, plenty of room for 4 adults. Good location near MGM/downtown Springfield."
The price is AU$397
per night
10 June - 11 June
Thomas's Cozy Duplex - Centrally Located
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (20)
"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Easthampton Vacation Rental - Walk to Breweries!
9.4 out of 10, Exceptional, (3)
"This is one of the best properties in the Pioneer Valley for the price. Comfortable, clean, and central. The team at Evolve and the local property manager are incredibly kind and responsive. Check-in was flawless and our stay was an absolute 10/10 from top to bottom. Keep in mind this property does have stairs to get to the bathroom and bedrooms, but the double railings made it a breeze for my elderly parents. The location is unbeatable, so many things to do within a five minute walk from the...
Easthampton Vacation Rental - Walk to Breweries!
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
9.4 out of 10, Exceptional, (6)
"Cute cabin in a beautiful private setting. Very peaceful and surrounded by nature."
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
Private Cabin On Over 12 Acres Of Woods!
10.0 out of 10, Exceptional, (3)
"The cabin is cozy and absolutely beautiful. We had everything we needed for a a relaxing stay in The Berkshires. Thanks for the comfort and welcoming hospitality."
The price is AU$2,141
per night
6 July - 7 July
Private Cabin On Over 12 Acres Of Woods!
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See all available properties in Montgomery
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.

Other types of properties in Montgomery you may be interested in

MGM Springfield
4.0 star property
8.8 out of 10, Excellent, (1015)
"The attention to detail particularly in the hotel lobby was impressive. The location was great, staff excellent. The rooms were clean, quiet and very comfortable. Easy access in and out to the highway. Overall, very well laid out and a pleasant experience."
The price is AU$240
per night
10 June - 11 June
MGM Springfield
Fairfield Inn & Suites by Marriott Springfield Enfield
2.5 star property
8.8 out of 10, Excellent, (817)
"Close to where I needed to be for business. "
The price is AU$192
per night
23 June - 24 June
Fairfield Inn & Suites by Marriott Springfield Enfield
DoubleTree by Hilton Hartford - Bradley Airport
4.0 star property
8.0 out of 10, Very good, (1012)
"Hallways could have been vaccumed was there for 4 nights and same stuff was in hallways and pool area had towels on the floor for 3 days "
The price is AU$236
per night
1 July - 2 July
DoubleTree by Hilton Hartford - Bradley Airport
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.

Everything you need to know about Montgomery holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Montgomery holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montgomery holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montgomery holiday rentals we have selected for you start as low as AU$262 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Montgomery rentals

At Expedia, we put the best Montgomery holiday 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 holiday.

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 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?

Cozy apartment located in quiet Williamsburg: This holiday home rental outside of Montgomery is in a rural location, and equipped with air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Montgomery?

Explore the area and family-friendly sights such as Six Flags New England, or get out into nature at a spot like Westfield River. Holyoke Mall and Big E are a couple of places you'll find in the wider area.

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.

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