Photo by Jim Stamatopoulos

Holiday Homes in Monson

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Featured Holiday Homes in Monson

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (180)
"Overall a wonderful stay. This is a duplex and the owner lives next door. Nice neighborhood and beautiful view"
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

9.8 out of 10, Exceptional, (102)
"Very nice, well equipped, absolutely beautiful view!!!!!!"
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

PICON COZY

7.6 out of 10, Good, (54)
"I booked this for my daughter who is looking to relocate to Western Mass from Central Mass and it was perfect for her. The host was extra helpful and accomodating, and while it was a small and simple space, she was very comfortable and cozy. She would definitely stay again."
The price is AU$264
includes taxes & fees
22 Dec - 23 Dec
PICON COZY

Large relaxing house in 25 acres of private woods with lake access.

10.0 out of 10, Exceptional, (16)
"Excellent home in the woods. All as advertised, my family and I thoroughly enjoyed it. Communication with the owner was excellent. 10/10, we’ll be back next time we’re in the area"
Large relaxing house in 25 acres of private woods with lake access.

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location near restaurants and stores. House is "
The price is AU$606
includes taxes & fees
19 Dec - 20 Dec
Charming 4Bds+1crib house with patio Amherst Center

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

9.6 out of 10, Exceptional, (29)
"It was nice stay!"
The price is AU$495
includes taxes & fees
22 Dec - 23 Dec
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

The Creation Station is a cozy place so make yourself at home.

10.0 out of 10, Exceptional, (61)
"We needed a pet friendly location to stay for one night. This place is amazing. Very unconventional and much more than I needed for my family of four but I would recommend it highly. The host was very helpful and friendly. The property would be great for an adult birthday or an extended family get together. "
The price is AU$437
includes taxes & fees
26 Nov - 27 Nov
The Creation Station is a cozy place so make yourself at home.

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!

Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!

10.0 out of 10, Exceptional, (9)
"Beautifully appointed home on a beautiful lake in Woodstock, CT. We enjoyed kayaking on the lake, visiting nearby orchards and hiking the many scenic trails nearby. Many great restaurants in the area as well. Although we did not partake, there is a great rail trail nearby for hiking, walking, etc. The home listing is very accurate, the kitchen is well equipped, and the cleanliness of the home is top notch. In addition, the hosts Heather and Dan, were very responsive and were...
The price is AU$800
includes taxes & fees
1 Dec - 2 Dec
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!

Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

9.8 out of 10, Exceptional, (27)
"Very quiet home. Well equipped for a large family "
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

Château at Longmeadow, Luxurious Home, 5 min from MGM & Basketball Hall of Fame

9.2 out of 10, Wonderful, (5)
"Several colleagues and I stayed here for a conference in Springfield. While the location was fairly convenient and the house was very clean, there were areas that could be improved upon. We loved having several bathrooms but there was only one roll of toilet paper in each bathroom and no extras for replacements. We ended up having to buys some. Instead of having king beds in every room, it would be nice to have one king bedroom and to have multiple beds in the other bedrooms. The basement is...
The price is AU$1,674
includes taxes & fees
24 Nov - 25 Nov
Château at Longmeadow, Luxurious Home, 5 min from MGM & Basketball Hall of Fame

Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

9.8 out of 10, Exceptional, (60)
"This property is amazing! We had such a great weekend - the water view is incredible and we had everything we needed for a cozy stay. Thank you!!"
The price is AU$801
includes taxes & fees
4 Dec - 5 Dec
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

Hadley Amherst Location.Explore the Valley Colleges!

10.0 out of 10, Exceptional, (129)
"The house was amazing, clean and comfortable. The area was great and very close to restaurants and shopping. I just can’t say enough good things about our experience. If I could give it more than five stars I would. "
Hadley Amherst Location.Explore the Valley Colleges!

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

10.0 out of 10, Exceptional, (47)
"What a gem this cute house was on the lake! The owners didn’t skip a beat with the attention to detail. It had everything and was so clean. Communication was spot on. We will definitely book again the next time we come to CT! We already miss waking up with coffee and watching the sun come up over the lake. "
The Bungalow at Eagleville Lake Under 3 miles to UCONN!

Hilda’s Riverside Retreat

9.8 out of 10, Exceptional, (24)
"This is a great place to stay. Clean and cozy and the hosts were great to work with. We had a breaker trip and Kelly was here within 10 min to fix it."
Hilda’s Riverside Retreat

Etinde House is located ten minutes from Umass, Amherst College, Hampshire mall, Mount Holyoke College and a minute from Hampshire College

6.6 out of 10, (11)
"This house is one of the worst places I have ever stayed. I booked for 13 people and only 2 of the 3 showers worked which they never disclosed to us. The house was a total pigsty. Dirty dishes in the sink. Old food in the fridge. Frozen food in the freezer and the freezer was disgusting with frozen spills that looked like they were there for years. Holes in the walls & doors, burn marks on the counters, dirty table cloth. Bathrooms were filthy. No shades on 90 % of the windows & no curtains at...
The price is AU$2,774
includes taxes & fees
30 Nov - 1 Dec
Etinde House is located ten minutes from Umass, Amherst College, Hampshire mall, Mount Holyoke College and a minute from Hampshire College

Lake House in Sturbridge w/All the Views!

9.8 out of 10, Exceptional, (6)
"We had a great time in Sturbridge. Can't beat the location of this house - it's absolutely beautiful, and very close to Old Sturbridge Village and a cute coffee shop we frequented during the long weekend. Everything was nice and clean, the hot tub was great, and it was easy to check in. The beds are comfortable and it was nice to not have to worry about the linens upon checkout. The host replied super promptly when we had questions about the location of trash/recycling bins, and when there was...
The price is AU$1,882
includes taxes & fees
30 Nov - 1 Dec
Lake House in Sturbridge w/All the Views!

Full family home 200 ft from the lake shore. Dog friendly!

10.0 out of 10, Exceptional, (5)
"Great location for our family visit. Property was very clean. Host very responsive. The beautiful sunrises over the lake were an additional bonus!"
The price is AU$904
includes taxes & fees
8 Dec - 9 Dec
Full family home 200 ft from the lake shore. Dog friendly!

Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest

10.0 out of 10, Exceptional, (49)
"5 of us stayed here for a week while we were at an event nearby. The place is gorgeous, huge, impecably clean, and for our purposes very convenient. We particularly appreciated the nice touches of a bottle of wine and some snacks, and the large and very functional washing machine/dryer setup, We’re immediately trying to rebook for a trip next year!. We met the host once during our stay and they delightfully gave us a tour and he made sure everything was going well. Lovely to have a VRBO...
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest

"Duck Rock" Lakefront House with 200' Private Waterfront

10.0 out of 10, Exceptional, (15)
"Loved the house"
"Duck Rock" Lakefront House with 200' Private Waterfront
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 Monson

Home in the woods

9.4 out of 10, Exceptional, (21)
"A perfect retreat in the woods - secluded, yet close enough by car to everything you need. Matt is easy to work with and a great communicator. We love it here and cannot wait to come back!"
Home in the woods

Massachusetts Vacation Rental w/ Deck

9.6 out of 10, Exceptional, (15)
"Excellent communication with owner, answered all questions immediately via text when we were onsite. Well maintained property with great basement for hanging out as a family. "
Massachusetts Vacation Rental w/ Deck

Lakefront Cottage w/ Covered Porch & Dock!

3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
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.
Beautiful view of the beach with palm trees

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