A riverbank with a fallen tree, dense green foliage, and a clear blue sky.

Brimfield Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Brimfield holiday rentals

Property grounds

1. 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, (9 reviews)
"Excellent communicative host with warm welcome and delightful amenities. Quiet neighborhood with plenty of parking."
United States
Pamela L.
The price is HK$1,380
HK$1,734 total
includes taxes & fees
29 Sept - 30 Sept
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Living area

2. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (38 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 HK$6,879
HK$12,518 total
includes taxes & fees
11 Sept - 12 Sept
Sleeps 15 • Pool • Retreat
Interior

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

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
7.0 out of 10, Good, (2 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is HK$745
HK$1,007 total
includes taxes & fees
13 Sept - 14 Sept
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Exterior

4. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is HK$1,376
HK$2,026 total
includes taxes & fees
14 Sept - 15 Sept
Dove Cabin up in the Trees
Terrace/patio

5. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (48 reviews)
"Great place, amazing lake!"
United States
megan g.
The price is HK$1,019
HK$2,550 total
includes taxes & fees
11 Sept - 12 Sept
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Living area

6. Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat

Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Holland
10.0 out of 10, Exceptional, (1 review)
"Cute place! Susan was a great host and the cabin was perfect for a qick getaway weekend and some reconnection with mother nature.."
United States
Jessica K.
The price is HK$1,341
HK$1,906 total
includes taxes & fees
14 Sept - 15 Sept
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Interior

7. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is HK$447
HK$1,103 total
includes taxes & fees
12 Sept - 13 Sept
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Property grounds

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (18 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
The price is HK$470
HK$1,599 total
includes taxes & fees
10 Sept - 11 Sept
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Interior

9. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is HK$1,176
HK$2,487 total
includes taxes & fees
14 Sept - 15 Sept
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Living area

10. Serenity meets Taradise

Serenity meets Taradise
Union
The price is HK$847
HK$1,356 total
includes taxes & fees
14 Sept - 15 Sept
Serenity meets Taradise
Exterior

11. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful farm that’s perfect little getaway for one weekend"
United States
Justyn M.
The price is HK$1,150
HK$2,491 total
includes taxes & fees
17 Sept - 18 Sept
Treehouse - Countryside - Farm Animals - Fire Pit
Property grounds

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

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.8 out of 10, Exceptional, (24 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
The price is HK$1,490
HK$1,782 total
includes taxes & fees
14 Sept - 15 Sept
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Interior

13. Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.6 out of 10, Exceptional, (11 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
Trainmaster's Inn - Caboose
Exterior

14. Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (39 reviews)
"We had a nice stay in this cabin by the lake. It was close to UCONN so the convenience of the location was wonderful. "
United States
Jennifer P.
The price is HK$1,446
HK$2,871 total
includes taxes & fees
17 Sept - 18 Sept
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Living area

15. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (37 reviews)
"The place was really nice! Very clean and well decorated. We had a great short stay and would definitely book it again in the future."
United States
Emily O.
The price is HK$1,235
HK$1,661 total
includes taxes & fees
14 Sept - 15 Sept
Newly Built Barn Loft in Pioneer Valley
Outdoor dining

16. 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, (35 reviews)
"This was an amazing nightly rate for the region, and a lovely place to visit. I'm so glad we found it and was available! Brent and family take great care of the place, and it was so magical waking up and seeing horses just a few feet from the window. We had fun playing games under the gazebo while horses munched on hay. There's lots of good hiking in the area too. The suite had everything we needed like extra blankets, kitchen wares, games, and a great shower too. Highly recommended!"
United States
Elizabeth
The price is HK$1,166
HK$2,094 total
includes taxes & fees
16 Sept - 17 Sept
Serene 1-bedroom suite on 75 acre horse property
Exterior

17. The Little Blue Bird

The Little Blue Bird
Willington
10.0 out of 10, Exceptional, (1 review)
"Great place! Great communication! Highly recommended for 1-2 people."
United States
Jeff G.
The price is HK$776
HK$1,275 total
includes taxes & fees
11 Sept - 12 Sept
The Little Blue Bird
Interior

18. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (41 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is HK$988
HK$1,518 total
includes taxes & fees
14 Sept - 15 Sept
The Tree House at Underhill Hollow
Exterior

19. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (24 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
The price is HK$988
HK$1,473 total
includes taxes & fees
11 Sept - 12 Sept
Wizard's Roost at Underhill Hollow
Room

20. 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
9.6 out of 10, Exceptional, (9 reviews)
"This is a real gem of a find! I loved our stay here. GPS does take you to the back of the building but it’s located next to a large parking lot. Plenty of parking which was great for us because we have an extended cab f350 ford that does not fit into most parking spaces. The other great thing about this house is multiple showers and bathrooms. This is so rare in a CT house. I must’ve searched for hours. The host Pam was super friendly and was so quick to respond. The house was super stocked with...
United States
Jenny
The price is HK$1,284
HK$2,933 total
includes taxes & fees
15 Sept - 16 Sept
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
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 Brimfield Hotel Reviews

Hilton Garden Inn-Springfield, MA

Hilton Garden Inn-Springfield, MA

10/10 Excellent
"Clean room"
Jaysharie 2-night trip
Posted 1 hour ago
Hilton Garden Inn-Springfield, MA

Find out more about Brimfield

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

  • View our selection of featured holiday rentals in Brimfield
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Look no further and take a look at our great range of rental properties in Brimfield!

Frequently asked questions

Can I find holiday rentals in Brimfield?

Yes, there are holiday rentals close to the most popular sights in Brimfield, or you can select a more secluded option if you're looking for a relaxing stay. Brimfield is known for its restaurants and entertainment choices. Make sure you have time to check out the shopping while you're in the area.

What are some of the best holiday rentals that Brimfield has to offer?

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8: This highly rated holiday home rental in Brimfield is located in a rural location, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Our travellers also rate Sleeps 15 • Pool • Retreat as a favourite home for rent in Brimfield.

How many holiday rentals are there in Brimfield?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Brimfield stay.

What’s there to see and do in Brimfield?

East Brimfield Lake and Quaboag River are a couple of lovely local spots to get outside and enjoy nature. Brimfield Town Hall and Brimfield Public Library are other places to visit while you're in town.

What’s a holiday rental in Brimfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Brimfield. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.