Book Holiday Homes in Brimfield

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Featured Holiday Homes in Brimfield

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms

Worcester MA
The price is AU$753 per night from 31 Dec to 1 Jan
AU$753
31 Dec - 1 Jan 2026
includes taxes & fees
With a stay at this vacation home in Worcester, you'll be within a 5-minute drive of Bowlero Worcester and College of the Holy Cross.
Opens in a new windowSpacious 4-bedroom with four and half bathrooms
Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow

North Grosvenordale CT
This vacation home is 3.5 mi (5.6 km) from Thompson International Speedway and 4.8 mi (7.8 km) from Bradley Playhouse.
Opens in a new windowWizard's Roost at Underhill Hollow
Tiny Home with AC and WiFi in lovely Ludlow

Tiny Home with AC and WiFi in lovely Ludlow

Ludlow MA
The price is AU$226 per night from 29 Dec to 30 Dec
AU$226
29 Dec - 30 Dec
includes taxes & fees
With a stay at this vacation home in Ludlow, you'll be within a 15-minute drive of MGM Springfield and Naismith Memorial Basketball Hall of Fame.
Opens in a new windowTiny Home with AC and WiFi in lovely Ludlow
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Amazing lake house with everything you need!

Amazing lake house with everything you need!

Ashford CT
Located in Ashford, this vacation home is on a lake, within a 10-minute drive of Tinkerville Brook Reserve and Iron Mine Valley Preserve.
Opens in a new windowAmazing lake house with everything you need!
Updated 3Bedroom. 5beds group ready.Walk to the Casino and play game of Pool.

Updated 3Bedroom. 5beds group ready.Walk to the Casino and play game of Pool.

2 out of 5
Springfield MA
Located in Springfield (South End), this vacation home is within a 15-minute walk of MGM Springfield and Naismith Memorial Basketball Hall of Fame.
Opens in a new windowUpdated 3Bedroom. 5beds group ready.Walk to the Casino and play game of Pool.
The Tree House at Underhill Hollow

The Tree House at Underhill Hollow

Thompson CT
This vacation home is 3.5 mi (5.6 km) from Thompson International Speedway and 4.8 mi (7.8 km) from Bradley Playhouse.
Opens in a new windowThe Tree House at Underhill Hollow
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

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

Springfield MA
The price is AU$481 per night from 4 Jan to 5 Jan
AU$481
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at this vacation home in Springfield (Forest Park), you'll be within a 5-minute drive of MGM Springfield and Naismith Memorial Basketball Hall of ...
Opens in a new windowUpscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
3-bedroom house in perfect Springfield with WiFi, AC

3-bedroom house in perfect Springfield with WiFi, AC

2 out of 5
Springfield MA
With a stay at this vacation home in Springfield (Pine Point), you'll be within a 10-minute drive of MGM Springfield and Naismith Memorial Basketball Hall of ...
Opens in a new window3-bedroom house in perfect Springfield with WiFi, AC
Leicester Lake Front Home, Come Relax!

Leicester Lake Front Home, Come Relax!

Leicester MA
Located in Leicester, this vacation home is on the waterfront, within a 15-minute drive of Vibra Hospital of Western Massachusetts - Central Campus and Burnside ...
Opens in a new windowLeicester Lake Front Home, Come Relax!
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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.

Brimfield Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Brimfield vacation homes are the perfect way for you to wing it.

Holiday houses in Brimfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Brimfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Brimfield adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Brimfield with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Brimfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Brimfield Holiday Homes essential information

Accommodation
112 Holiday Homes
Lowest Price
AU$133
Highest Price
AU$753
Popular accommodation
Spacious 4-bedroom with four and half bathrooms, Wizard's Roost at Underhill Hollow, Tiny Home with AC and WiFi in lovely Ludlow, Amazing lake house with everything you need! , Updated 3Bedroom. 5beds group ready.Walk to the Casino and play game of Pool., The Tree House at Underhill Hollow, Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!, 3-bedroom house in perfect Springfield with WiFi, AC, Leicester Lake Front Home, Come Relax!

Top trending hotels in Brimfield

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

2 out of 5
Brimfield MA
The price is AU$269 per night from 4 Jan to 5 Jan
AU$269
4 Jan - 5 Jan 2026
includes taxes & fees
Located in Brimfield, this vacation home is in a rural location, within a 5-minute drive of Brimfield State Forest and Wales Public Library.
Opens in a new windowLittle House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way Springfield MA
The price is AU$286 per night from 4 Jan to 5 Jan
AU$286
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at MGM Springfield, you'll be centrally located in Springfield, within a 10-minute walk of MassMutual Center and Naismith Memorial Basketball Hall ...
Opens in a new windowMGM Springfield
Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 out of 5
277 Main Street (RT 131) Sturbridge MA
Fully refundableReserve now, pay when you stay
The price is AU$133 per night from 4 Jan to 5 Jan
AU$133
4 Jan - 5 Jan 2026
includes taxes & fees
When you stay at Publick House Historic Inn and Country Motor Lodge in Sturbridge, you'll be in the historical district, within a 5-minute drive of Old Sturbridge ...
Opens in a new windowPublick House Historic Inn and Country Motor Lodge
Save an average of 15% on thousands of hotels when you're signed in
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street Springfield MA
Fully refundableReserve now, pay when you stay
The price is AU$187 per night from 1 Jan to 2 Jan
AU$187
1 Jan - 2 Jan 2026
includes taxes & fees
A stay at La Quinta Inn & Suites by Wyndham Springfield MA places you in the heart of Springfield, within a 5-minute drive of Paramount Theater and MGM ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham Springfield MA
Don't see what you're looking for?
See all available properties in Brimfield
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.