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Monson Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Monson vacation rentals

A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

1. Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.

Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.
Stafford
9.6 out of 10, Exceptional, (50 reviews)
"Wonderful stay. Perfect spot on lake w kayaks already there very clean and had everything we needed!! We loved our stay and so relaxed."
United States
Lisa S.
Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

2. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (12 reviews)
"What a beautiful set up for a pet friendly family stay - candles lit upon arrival and a child’s room filled with toys ready to be enjoyed."
United States
Gregory C.
The price is CA $220
CA $264 total
includes taxes & fees
Nov 12 - Nov 13
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A wooden cabin with a glass upper floor, surrounded by a forest.

3. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (39 reviews)
"Excellent location for a quiet and relaxing getaway. The cabin was clean and well outfitted. Our host greeted us, talked about the history of the property, kayaking around the lake was great, such a good idea for an old youth camp with so much potential. We’ll definitely be returning for another stay"
United States
Zachary C.
The price is CA $248
CA $350 total
includes taxes & fees
Nov 12 - Nov 13
Dove Cabin up in the Trees
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

4. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
6.0 out of 10, (3 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is CA $140
CA $176 total
includes taxes & fees
Nov 22 - Nov 23
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A white building with a porch and a stone border.

5. Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Somers
9.8 out of 10, Exceptional, (12 reviews)
"Fantastic host. Went out of their way to make our stay very pleasant. Beautiful historic home that felt very welcoming and cozy even though it is so big!"
United States
John
The price is CA $217
CA $487 total
includes taxes & fees
Nov 16 - Nov 17
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
A two-story house with a front porch, a small entryway, and a set of stairs leading to the front door.

6. Bling nest

Bling nest
Ludlow
The price is CA $254
CA $566 total
includes taxes & fees
Nov 15 - Nov 16
Bling nest
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

7. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (24 reviews)
"The place was unique and cozy. The hosts were very friendly and our stay was great"
United States
Stacy
The price is CA $166
CA $380 total
includes taxes & fees
Nov 22 - Nov 23
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A living room with two brown leather sofas, a glass coffee table, a white rug, a ceiling fan, and a door with curtains.

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

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
8.8 out of 10, Excellent, (26 reviews)
"The stove was broken, which we were made aware of and there was an offer to cancel for us. We chose to still go because we needed a place to stay. The stove was in the middle of the kitchen when we arrived. I did decide to cancel the second night in the owner, said they would refund us, but they only refund part of the second night."
United States
Gladys B.
The price is CA $254
CA $530 total
includes taxes & fees
Nov 15 - Nov 16
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
A modern reception area with a counter, two chairs, a small table, and a carpeted floor.

9. 1 King Bed|Smoking, Micfridge

1 King Bed|Smoking, Micfridge
Enfield
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $97
CA $111 total
includes taxes & fees
Nov 17 - Nov 18
1 King Bed|Smoking, Micfridge
A living room with two sofas, a coffee table, and a potted plant.

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

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Boston Road
9.0 out of 10, Wonderful, (14 reviews)
"Our stay was fantastic. Check in was super smooth and the host was very responsive. I would definitely stay here again in the future."
United States
Nicholas T.
The price is CA $254
CA $530 total
includes taxes & fees
Nov 14 - Nov 15
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
A wooden cabin with a balcony and stairs, surrounded by trees.

11. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful treehouse with everything you need. My kids loved picking blueberries and meeting the farm animals!"
United States
Lauren B.
The price is CA $197
CA $402 total
includes taxes & fees
Nov 17 - Nov 18
Treehouse - Countryside - Farm Animals - Fire Pit
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

12. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"The room was very clean and modern. The check-in process was easy and I had the best rest that I had in a long time. Being in the lower level with no windows provided a very quiet and dark ambiance at night. There is ample lighting throughout the unit if needed though, you can really unplug here. I would definitely stay here again"
United States
Kebreab H.
The price is CA $80
CA $319 total
includes taxes & fees
Nov 16 - Nov 17
Modern Studio Ideal for Traveling Professionals
Exterior

13. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful apartment! Amazing finishes, well appointed, pristine apartment in Holyoke. Great communication from the host. A quick trip to Dam Coffee Shop for great coffee and breakfast options. Not too far from Stop & Shop for food and short ride to highway. Would book this spot again."
United States
Yvonne A.
The price is CA $81
CA $426 total
includes taxes & fees
Nov 22 - Nov 23
Work, Play & Stay! Apt Near Holyoke Medical Center
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

14. Serene 1-bedroom suite on 75 acre horse property

Serene 1-bedroom suite on 75 acre horse property
Belchertown
10.0 out of 10, Exceptional, (40 reviews)
"We had a great, restorative stay in Liberty Woods. It is a lovely oasis with kind humans, friendly animals and beautiful horses in a beautiful setting."
United States
Anna O.
The price is CA $213
CA $367 total
includes taxes & fees
Nov 30 - Dec 1
Serene 1-bedroom suite on 75 acre horse property
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

15. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (40 reviews)
"It was a beautiful property. Well-tended and all the amenities. Loved the view in morning and evening of mountains and sun / moon."
United States
Daniel C.
The price is CA $1,398
CA $2,504 total
includes taxes & fees
Nov 17 - Nov 18
Sleeps 15 • Pool • Retreat
A grassy outdoor area with a hammock, chairs, and a stone wall.

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

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.6 out of 10, Exceptional, (28 reviews)
"This was a super cozy ,cute place to stay . Host had muffins , juice and milk for us. The property was quiet and very peaceful."
United States
theresa H.
The price is CA $229
CA $261 total
includes taxes & fees
Nov 12 - Nov 13
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A modern living room with a leather sofa, a coffee table, and a dining table. There are two windows providing natural light, a ceiling light fixture, and a trash can.

17. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (39 reviews)
"Great place for a couple to stay. Hostess was fantastic. We had everything we needed. Would definitely recommend and would stay again!"
United States
Doreen R.
The price is CA $254
CA $325 total
includes taxes & fees
Nov 15 - Nov 16
Newly Built Barn Loft in Pioneer Valley
A two-story house with a porch, a flag, and potted plants.

18. The Little Blue Bird · 5 Mi UConn · 2 Min I-84

The Little Blue Bird · 5 Mi UConn · 2 Min I-84
Willington
9.4 out of 10, Exceptional, (3 reviews)
"Great place! Great communication! Highly recommended for 1-2 people."
United States
Jeff G.
The price is CA $150
CA $232 total
includes taxes & fees
Nov 16 - Nov 17
The Little Blue Bird · 5 Mi UConn · 2 Min I-84
A modern living room with a black leather sofa set, a glass coffee table, and a patterned rug.

19. Beautifully Renovated First-Floor Apartment Getaway

Beautifully Renovated First-Floor Apartment Getaway
Forest Park
9.6 out of 10, Exceptional, (7 reviews)
"This was a spacious 4 bedroom. Clean and smooth check in and out. Thank you for having me and my guest "
United States
Alyssa A.
The price is CA $235
CA $464 total
includes taxes & fees
Nov 12 - Nov 13
Beautifully Renovated First-Floor Apartment Getaway
A modern living room with a sofa, a coffee table, and a red patterned rug.

20. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (53 reviews)
"House was super clean, coffee was a nice surprise. Comfy beds, quiet street. Super close to the Big E. Thanks Rose!"
United States
Brian
The price is CA $254
CA $487 total
includes taxes & fees
Nov 15 - Nov 16
Cozy & Spacious Entire Home in Springfield
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

A hotel entrance with a covered walkway, columns, and a brick facade.
Holiday Inn Express & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG
Sturbridge

10/10 Excellent

Great stay
Canada
Tyler
Reviewed May 3, 2026
Holiday Inn Express & Suites Sturbridge by IHG

Find out more about Monson

Everything you need to know about Monson vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Monson vacation rental for you. At Expedia, you can take your pick from private vacation 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 Monson vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Monson vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Monson. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Monson vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Monson vacation rentals we have selected for you start as low as CA $80 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Monson rentals

At Expedia, we put the best Monson vacation 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 Monson 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 Monson vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Monson. 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

Are there vacation rentals in Monson?

Yes, we give you a choice of vacation rentals near the most popular attractions in Monson, or you can select a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Monson has to offer?

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8: This vacation home rental near Monson is located in a rural location and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Monson?

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

What’s a vacation rental in Monson like?

A vacation rental is a private property you can stay in for a long or short time in Monson. Vacation rentals feature amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for families.