Photo by Jim Stamatopoulos

Monson Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Monson holiday rentals

Interior
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Holiday Home in Ware

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
2.0 star property
10.0 out of 10, Exceptional, (3)
"We had a great time the place was clean and the owner was nice. I would definitely recommend."
United States
Laura B.
The price is HK$1,027
HK$1,250 total
includes taxes & fees
16 Dec - 17 Dec
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Dining
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Holiday Home in Woodstock

Secluded 2-Acre Lakefront Home! Book Your Getaway!
9.8 out of 10, Exceptional, (76)
"Lovely stay on the lake, we enjoyed the location and the kayaks on the lake. "
United States
Lucy H.
The price is HK$2,032
HK$3,837 total
includes taxes & fees
14 Dec - 15 Dec
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Fridge, microwave, oven, stovetop
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Apartment in Amherst

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
9.4 out of 10, Exceptional, (17)
"Great property! Thank you for a wonderful stay."
United States
David
The price is HK$1,744
HK$3,261 total
includes taxes & fees
15 Dec - 16 Dec
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Smart TV
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Holiday Home in Boston Road

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
9.2 out of 10, Wonderful, (13)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
The price is HK$981
HK$2,472 total
includes taxes & fees
13 Dec - 14 Dec
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Exterior detail
Elm Suite with a Private Bathroom in front of Smith College Quadrangle

Apartment in Northampton

Elm Suite with a Private Bathroom in front of Smith College Quadrangle
9.8 out of 10, Exceptional, (23)
"Gorgeous building, clean and cozy spot to stay. "
United States
Grace
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Exterior
Treehouse - Countryside - Farm Animals - Fire Pit

Cabin in Willington

Treehouse - Countryside - Farm Animals - Fire Pit
9.4 out of 10, Exceptional, (28)
"My husband and I were exploring a number of birding hotspots in the quiet corner and decided to try the treehouse. We woke to the dawn bird chorus (without any ambient road noise). Just dreamy!"
United States
Jennifer H.
The price is HK$1,058
HK$2,369 total
includes taxes & fees
6 Jan - 7 Jan 2026
Treehouse - Countryside - Farm Animals - Fire Pit
Living area
Newly Renovated 2 floor Getaway

Apartment in Forest Park

Newly Renovated 2 floor Getaway
3.5 star property
The price is HK$3,420
HK$5,048 total
includes taxes & fees
23 Dec - 24 Dec
Newly Renovated 2 floor Getaway
Exterior
Bungalow 19 by the lake in Brimfield

Holiday Home in Brimfield

Bungalow 19 by the lake in Brimfield
2.0 star property
10.0 out of 10, Exceptional, (4)
"Beautiful house, really cozy and private. Clean and tidy. Our host was helpful and accommodating. Would definitely stay there again. "
United States
Samantha W.
Bungalow 19 by the lake in Brimfield
Living area
Charming 2-bedroom house in Terrific Sturbridge with AC

Holiday Home in Sturbridge

Charming 2-bedroom house in Terrific Sturbridge with AC
2.0 star property
10.0 out of 10, Exceptional, (1)
"We enjoyed our stay! The host was very responsive. The house was in a nice quite area. The "shed bar" was a nice and fun touch! "
United States
Cheryl L.
Charming 2-bedroom house in Terrific Sturbridge with AC
1 bedroom, free WiFi, bed sheets
HOMEY HOMEY

Apartment in Sixteen Acres

HOMEY HOMEY
2.8 out of 10, (5)
"We did not even stay. The upstairs has access to the basement door so I did not at all feel comfortable. And there is a terrible mildew smell. "
United States
Erin N.
The price is HK$560
HK$1,297 total
includes taxes & fees
14 Dec - 15 Dec
HOMEY HOMEY
Property grounds
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Holiday Home in Sturbridge

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
9.8 out of 10, Exceptional, (89)
"Very Clean, great location"
United States
Anonymous traveller
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Exterior
Dove Cabin up in the Trees

Cabin in Holland

Dove Cabin up in the Trees
9.8 out of 10, Exceptional, (27)
"Beautiful quaint cabin "
United States
susan n.
Dove Cabin up in the Trees
Dining
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT

Holiday Home in Manchester

Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
9.8 out of 10, Exceptional, (7)
"Spacious, clean and comfortable home. Nice neighborhood near a nice park and trails . Beds were comfortable, kitchen had the pots and pans we needed for dinner and breakfast. Perfect space for us and our 3 adult boys. "
United States
Denise L.
The price is HK$926
HK$2,177 total
includes taxes & fees
16 Dec - 17 Dec
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
Private kitchen
Tiny Home with AC and WiFi in lovely Ludlow

Holiday Home in Ludlow

Tiny Home with AC and WiFi in lovely Ludlow
8.4 out of 10, Very good, (9)
"Good stay for an overnight in the area, location was a little tricky to find at night but once I did it was easy to get in. Had all the amenities needed for a short stay and is near the highway for quick on and off."
United States
Matthew H.
The price is HK$615
HK$1,164 total
includes taxes & fees
16 Dec - 17 Dec
Tiny Home with AC and WiFi in lovely Ludlow
Exterior
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

Holiday Home in West Brookfield

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
10.0 out of 10, Exceptional, (15)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
United States
JUNE
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Interior
Amazing lake house with everything you need!

Holiday Home in Ashford

Amazing lake house with everything you need!
9.8 out of 10, Exceptional, (22)
"Great time, lovely location, easy to access and beautiful lake!"
United States
Sam L.
Amazing lake house with everything you need!
Outdoor dining
The Lake House

Holiday Home in Coventry Lake

The Lake House
9.8 out of 10, Exceptional, (20)
"Very nice place, we enjoyed our stay!"
United States
David G.
The Lake House
Interior
PICON COZY

Holiday Home in Sixteen Acres

PICON COZY
7.4 out of 10, Good, (69)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
United States
Linda W.
The price is HK$591
HK$1,333 total
includes taxes & fees
23 Dec - 24 Dec
PICON COZY
Interior
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Apartment in Forest Park

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
9.0 out of 10, Wonderful, (28)
"This home was great. It had everything our large group needed and was as advertised. The owner was great to communicate with. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
The price is HK$2,033
HK$4,081 total
includes taxes & fees
14 Dec - 15 Dec
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Property grounds
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Holiday Home in Spencer

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
10.0 out of 10, Exceptional, (200)
"Great time spent with family"
Canada
Marianne B.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
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 Monson Hotel Reviews

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

10/10 Excellent
"The staff have all been very friendly, the hot breakfast was so delicious and the room was clean and well taken care of."
Wendi 1-night trip
Posted 10 hours ago
La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

Find out more about Monson

Search for holiday rentals in Monson on Expedia! You can easily find your home rentals, villas, holiday apartments in Monson using one of the methods below:

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Look no further and take a look at our great range of rental properties in Monson!

Frequently asked questions

Are there holiday rentals in Monson?

Yes, there are holiday rentals close to the most popular sights in Monson, 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 Monson has to offer?

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6: This holiday home rental outside of Monson is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Monson?

Brimfield State Forest and Peaked Mountain are a couple of lovely local spots to get outside and enjoy nature. While here, Monson Town Hall and Cedar Swamp are other places worth a visit.

What’s a holiday rental in Monson like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Monson. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for small groups.