A calm lake surrounded by trees and a clear sky.

Holiday Homes in Webster

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Our top choices for Webster holiday homes

1. 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 AU$258
includes taxes & fees
4 Nov - 5 Nov
Wizard's Roost at Underhill Hollow

2. 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 AU$266
includes taxes & fees
5 Nov - 6 Nov
The Tree House at Underhill Hollow

3. 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 AU$258
includes taxes & fees
4 Nov - 5 Nov
SteamPunk Bunk House and Intergalactic Way Station

4. 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 AU$880
includes taxes & fees
4 Nov - 5 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!

5. 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 AU$658
includes taxes & fees
4 Nov - 5 Nov
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

6. 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 AU$621
includes taxes & fees
9 Nov - 10 Nov
Clifford Luxury Retreat 3BR Self Check In Home

7. 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 AU$684
includes taxes & fees
8 Nov - 9 Nov
Spacious 4-bedroom with four and half bathrooms

8. 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 AU$251
includes taxes & fees
4 Nov - 5 Nov
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

9. 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 AU$350
includes taxes & fees
4 Nov - 5 Nov
Cottage by the Castle – Downtown Spencer

10. 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 AU$354
includes taxes & fees
14 Nov - 15 Nov
Angel Sky Challenge

11. 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 AU$2,369
includes taxes & fees
5 Nov - 6 Nov
Sleeps 15 • Pool • Retreat

12. 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 AU$442
includes taxes & fees
4 Nov - 5 Nov
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

13. 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 AU$619
includes taxes & fees
22 Nov - 23 Nov
Worcester Lakefront Cottage Apt w/ Shared Dock!

14. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (11 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
The price is AU$414
includes taxes & fees
5 Nov - 6 Nov
Spacious, unique barn with beautiful views.

15. 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 AU$749
includes taxes & fees
15 Nov - 16 Nov
4-bedroom house in nice Holden with WiFi, AC

16. 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.
Lake House in Sturbridge w/All the Views!
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 Webster Hotel Reviews

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Webster Holiday Homes information

Number of reviews
436
Accommodation
111 Holiday Homes
Lowest Price
AU$251
Highest Price
AU$2,369