Holiday Homes in Leicester

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Check prices for these dates

Our top choices for Leicester holiday homes

1. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (9 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is NZ$400
includes taxes & fees
10 Nov - 11 Nov
Cottage by the Castle – Downtown Spencer

2. Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester Lakefront Cottage Apt w/ Shared Dock!
Worcester
9.4 out of 10, Exceptional, (19 reviews)
"The host was very accommodating and responsive. Great property in a great location, would stay again!"
United States
Michaela H.
The price is NZ$795
includes taxes & fees
22 Nov - 23 Nov
Worcester Lakefront Cottage Apt w/ Shared Dock!

3. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean location to stay."
United States
Mike O.
The price is NZ$844
includes taxes & fees
9 Nov - 10 Nov
Spacious 4-bedroom with four and half bathrooms

4. Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
The price is NZ$427
includes taxes & fees
9 Nov - 10 Nov
Angel Sky Challenge

5. 4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
10.0 out of 10, Exceptional, (3 reviews)
"Communication with owner was very responsive and timely. House was clean and as description. Any problems were immediately addressed by owner."
United States
larry d.
The price is NZ$1,154
includes taxes & fees
22 Nov - 23 Nov
4-bedroom house in nice Holden with WiFi, AC

6. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
8.0 out of 10, Very good, (1 review)
"The house was fine overall. There were just a few things that stood out - only 3 towels but we were 4, no baking sheet for the oven, lighting in the kitchen wasn’t great, couldn’t find the house or unit number and the lock box was hard to find. The main bed was very comfortable but the pillows were not."
United States
Laura P.
The price is NZ$571
includes taxes & fees
11 Nov - 12 Nov
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

7. The Christmas Cottage, 4BR New England Escape

The Christmas Cottage, 4BR New England Escape
Rutland
The price is NZ$1,323
includes taxes & fees
9 Nov - 10 Nov
The Christmas Cottage, 4BR New England Escape

8. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
9.8 out of 10, Exceptional, (98 reviews)
"very clean, wonderful location"
United States
Anonymous traveller
The price is NZ$836
includes taxes & fees
10 Nov - 11 Nov
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

9. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!!"
United States
Elizabeth G.
The price is NZ$314
includes taxes & fees
9 Nov - 10 Nov
Wizard's Roost at Underhill Hollow

10. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (46 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is NZ$324
includes taxes & fees
9 Nov - 10 Nov
The Tree House at Underhill Hollow

11. 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 NZ$315
includes taxes & fees
9 Nov - 10 Nov
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

12. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is NZ$314
includes taxes & fees
9 Nov - 10 Nov
SteamPunk Bunk House and Intergalactic Way Station

13. Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (25 reviews)
"Pictures don't do this house justice! Great communication from start to finish, very clean house & property, coolest house we've ever stayed at. Hope to stay again!"
United States
Mike T.
The price is NZ$1,365
includes taxes & fees
11 Nov - 12 Nov
Lake House in Sturbridge w/All the Views!

14. 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 NZ$391
includes taxes & fees
15 Nov - 16 Nov
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

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 NZ$3,093
includes taxes & fees
10 Nov - 11 Nov
Sleeps 15 • Pool • Retreat

16. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.6 out of 10, Excellent, (7 reviews)
"We loved our stay here. The home and the host were both exceptional. We highly recommend this home!"
United States
Martin G.
The price is NZ$782
includes taxes & fees
9 Nov - 10 Nov
Clifford Luxury Retreat 3BR Self Check In Home

17. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
The price is NZ$1,290
includes taxes & fees
10 Nov - 11 Nov
Entire home in Sterling, Massachusetts, United States

18. Cozy & Stylish 2-bedroom Home in Leominster

Cozy & Stylish 2-bedroom Home in Leominster
Leominster
The price is NZ$405
includes taxes & fees
9 Nov - 10 Nov
Cozy & Stylish 2-bedroom Home in Leominster

19. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (95 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is NZ$1,093
includes taxes & fees
10 Nov - 11 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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.

Learn more about Leicester

Tucked away in central Massachusetts, Leicester offers easy access to the elegant Hanover Theatre for the Performing Arts and historic Salisbury Mansion. Spend afternoons exploring nearby Regatta Point Beach, then catch exciting events at DCU Centre or shop at Auburn Mall just a short drive away.

A serene lake with autumn-colored trees reflecting on the water, surrounded by houses.