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Top Holiday Rentals in Montgomery

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (196)
"Amazing views, lovely cottage!"
The Clearing - Quiet - Close To Nature

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (218)
"Cabin was exactly what we were looking for in a weekend away. Great location, quiet, and had everything we needed. Hope to go back again soon! "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

5 bedroom in the center of Springfield .

9.0 out of 10, Wonderful, (8)
"As advertised, great communication, would stay there again!"
5 bedroom in the center of Springfield .

PICON COZY

7.4 out of 10, Good, (68)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
The price is £125
includes taxes & fees
23 Aug - 24 Aug
PICON COZY

Charming Chicopee Getaway

10.0 out of 10, Exceptional, (1)
"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. "
The price is £214
includes taxes & fees
9 Sept - 10 Sept
Charming Chicopee Getaway

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (37)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Linny’s Lake Retreat, Family-Friendly & Dock Access

9.8 out of 10, Exceptional, (22)
"Amazing place and great hosts! This place was perfect for us to stay while in town visiting family. Will definitely be staying here again"
Linny’s Lake Retreat, Family-Friendly & Dock Access

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

10.0 out of 10, Exceptional, (1)
"Smooth and straightforward check-in process. They were accommodating to our schedule and communicated everything in a timely manner. House was clean and everything looked as listed. Kitchen was well stocked with up to date appliances and plenty of utensils which was a nice surprise. Plenty of space for 7 of us, would suggest bringing an air mattress though if with a larger party. Overwhelming positive experience overall. "
The price is £291
includes taxes & fees
18 Aug - 19 Aug
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

HOMEY HOMEY

3.4 out of 10, (3)
"We checked out early. The place had mold/mildew. Power went out and the place was dark. Not suitable for human use without major renovations and updates."
The price is £126
includes taxes & fees
18 Aug - 19 Aug
HOMEY HOMEY

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

9.0 out of 10, Wonderful, (7)
"Great property! Thank you for a wonderful stay."
The price is £345
includes taxes & fees
2 Sept - 3 Sept
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

10.0 out of 10, Exceptional, (1)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
The price is £316
includes taxes & fees
7 Sept - 8 Sept
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Lakefront Bungalow

9.6 out of 10, Exceptional, (10)
"Nice location on water, clean, kitchen had all our needs--would stay there again."
Lakefront Bungalow

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

9.0 out of 10, Wonderful, (10)
"Comfortable, clean and well maintained property. I definitely will book again. "
The price is £250
includes taxes & fees
1 Sept - 2 Sept
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (44)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

10.0 out of 10, Exceptional, (68)
"From booking through check out everything about our experience was amazing! The host was very responsive and helpful with any questions I had. The space was very clean and the host had thought of everything guests could need. We will definitely book again when we travel to the area!"
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

9.6 out of 10, Exceptional, (33)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
The price is £250
includes taxes & fees
18 Aug - 19 Aug
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Little Longbow Lakefront Chalet

9.6 out of 10, Exceptional, (14)
"Our stay was great. The property was extremely clean and the host was absolutely amazing. The property is located on a pond which we could kayak and do some fishing. Just sitting on the beautiful deck overlooking the pond was relaxing. The property offered exactly what we were looking for for this trip. "
Little Longbow Lakefront Chalet
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

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?

Peace and quiet on the lake: This holiday home rental outside of Montgomery is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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. Tekoa Mountain Wildlife Management Area 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.