Montgomery Vacation Rentals

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Browse Select Montgomery Vacation Homes

Peace and quiet on the lake

9.6 out of 10, Exceptional, (209)
"This was a cozy tucked away location that seemed far away from everything which was exactly what we wanted. The host was extremely communicative before and during the stay. The house had fresh linens and towels as well as basic cleaning supplies. It was cozy for a wintery weekend in. We enjoyed snowshoeing on the frozen lake! Pet-friendly was a huge plus! "
Peace and quiet on the lake

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (5)
"I booked the weekend for my girlfriends birthday with a couple of her friends. The game room was a massive hit as was the propane fireplace outside. We also enjoyed watching the snow fall on the frozen lake. William was very responsive to messages and calls. We enjoyed our stay immensely and are hoping to come back in the summer"
Berkshires Lakefront Retreat

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
10.0 out of 10, Exceptional, (2)
"A great place for a family stay in downtown Amherst. "
The price is CA $303
CA $603 total
includes taxes & fees
Mar 24 - Mar 25
Charming 4Bds+1crib house with patio Amherst Center

Spacious 5-bedroom house steps from UMass Campus, with large backyard.

Spacious 5-bedroom house steps from UMass Campus, with large backyard.

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "
Amherst, Perfect Location, UMass, Smith, MHC!

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

PICON COZY

7.8 out of 10, Good, (60)
"I booked this for my elderly Mom and her adult granddaughter who were in town for the holidays and also awaiting a January 1 move in to a new apartment. Fidelis was attentive, kind, and responded quickly to any issues in the property. The place itself was truly like home away from home and convenient to stores, shopping and public transportation. I would recommend anyone looking for a cozy stay in Springfield to check it out. It is well worth the price. I would even say it is a bargain and...
The price is CA $107
CA $243 total
includes taxes & fees
Mar 2 - Mar 3
PICON COZY

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (57)
"More than expected, owner pays attention to detail, many amenities, spotless. All the comforts of home. Owner very prompt to answer any questions. Will definitely be booking this againRobbin and Rich Willis"
Linny's Updated Lakeview Cottage - Cozy & Modern

Hadley Amherst Location.Explore the Valley Colleges!

10.0 out of 10, Exceptional, (130)
"Wonderful, updated and well-stocked kitchen and IMMENSE refrigerator helped with making four mammoth feasts in a row for family, with grandkids and pooches underfoot. Terrific location, beautifully appointed house, and Colleen could not possibly be more responsive. Thanks for having us!!!"
Hadley Amherst Location.Explore the Valley Colleges!

Thomas's Cozy Duplex - Centrally Located

8.6 out of 10, Excellent, (10)
"The duplex was clean and quiet. The kitchen was stocked well enough for us to make dinner, although there was no kitchen towel for drying hands and dishes (very minor). Three bedrooms, two with a double/queen, one with a single, and it looked like the couch in the living room was a pull out. Beds were comfortable with plenty of bedding. Wi-fi worked well. Couldn't ask for anything more. I would stay here again if in the area. "
The price is CA $157
CA $383 total
includes taxes & fees
Mar 9 - Mar 10
Thomas's Cozy Duplex - Centrally Located

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

9.6 out of 10, Exceptional, (10)
"Clean and neat. Owner was very nice and easy to communicate with. "
The price is CA $236
CA $407 total
includes taxes & fees
Feb 28 - Mar 1
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

10.0 out of 10, Exceptional, (3)
"We had a lovely stay! The space was perfect for our group of 4 moms looking for a peaceful getaway. The host was very responsive. Only note for those visiting, rideshares (Uber and otherwise) are few and far between. Schedule ahead! We'd definitely stay again :)"
Berkshire Ski House on Lake Garfield w/HT By Great Barrington

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (6)
"We loved everything about this home! It fit us perfectly and we would love to rent it again!"
Historic Farmhouse Near Mountains & Colleges!

2 Bedroom Pet Friendly-near Hospitals, Six Flag, Big E

10.0 out of 10, Exceptional, (6)
"This is a nice property and the downstairs to a duplex. They provided snacks and plenty of bottled water. Blankets, shampoo, and soap were also onsite. The hosts are responsive, and communicative. It is a quiet area, but if there is someone staying upstairs you will hear walking above you. Overall a great place to stay if you're in the area!"
2 Bedroom Pet Friendly-near Hospitals, Six Flag, Big E

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

10.0 out of 10, Exceptional, (34)
"This is our second time staying here and it just the most perfect house. We rang in the new year with friends and all our kids. The house is so cozy, we played games fireside and cooked dinner every night. During the day we explored Stockbridge, Great Barrington and Lennox. The location is perfect. We also went snow tubing at butternut mountain and bosque mountain. We woke up to snow, there is nothing better than a cup of coffee and those beautiful snow covered views. Thank you Chris and Jane!...
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

9.2 out of 10, Wonderful, (7)
"Well our first impression was "oh wow" it was amazing. It was super clean. We loved the house and everything in it. Would stay again. Thank you Victoria for the amazing home you provided. "
The price is CA $171
CA $444 total
includes taxes & fees
Mar 5 - Mar 6
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Becket Home w/ 3-Season Porch: Walk to Lake Access

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was a clean, quiet spot for a nice weekend getaway. "
Becket Home w/ 3-Season Porch: Walk to Lake Access

Picturesque Lake House with 6 bedroom, 4 bath in Granby CT.

10.0 out of 10, Exceptional, (1)
"This was a great stay Home had everything we needed and was very comfortable and cozy. Great location. Nathania was very communicative and helpful. We will stay here again and recommend it enthusiastically. "
Picturesque Lake House with 6 bedroom, 4 bath in Granby CT.
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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Other property types in Montgomery

PICON COZY

7.8 out of 10, Good, (60)
"I booked this for my elderly Mom and her adult granddaughter who were in town for the holidays and also awaiting a January 1 move in to a new apartment. Fidelis was attentive, kind, and responded quickly to any issues in the property. The place itself was truly like home away from home and convenient to stores, shopping and public transportation. I would recommend anyone looking for a cozy stay in Springfield to check it out. It is well worth the price. I would even say it is a bargain and...
The price is CA $107
CA $243 total
includes taxes & fees
Mar 2 - Mar 3
PICON COZY

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

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

The Skyway

The price is CA $154
CA $471 total
includes taxes & fees
Mar 24 - Mar 25
The Skyway
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.