A calm lake surrounded by trees and a clear sky.

Holiday Homes in Webster

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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 Webster holiday homes

Interior

1. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is NZ$333
includes taxes & fees
14 Sept - 15 Sept
The Tree House at Underhill Hollow
Exterior

2. 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 NZ$323
includes taxes & fees
14 Sept - 15 Sept
Wizard's Roost at Underhill Hollow
Property grounds

3. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is NZ$323
includes taxes & fees
14 Sept - 15 Sept
SteamPunk Bunk House and Intergalactic Way Station
Property grounds

4. 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)
"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$326
includes taxes & fees
15 Sept - 16 Sept
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Terrace/patio

5. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (28 reviews)
"We loved our stay at this lakeside retreat. We were in town for a wedding and in between family gatherings we were able to relax by the lake. The house was comfortable and well stocked so we didn't have to buy every little thing. I would definitely stay again"
United States
Lisa R.
The price is NZ$1,266
includes taxes & fees
26 Sept - 27 Sept
Stunning Lakefront Escape! Book Your Dream Getaway!
Interior

6. 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$449
includes taxes & fees
14 Sept - 15 Sept
Angel Sky Challenge
Dining

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (89 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$1,302
includes taxes & fees
14 Sept - 15 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Private kitchen

8. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (18 reviews)
"Perfect location"
United States
Harmony F.
The price is NZ$886
includes taxes & fees
14 Sept - 15 Sept
Spacious 4-bedroom with four and half bathrooms
Interior

9. Game Room + Bar Lounge, 35 Min to Boston

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is NZ$484
includes taxes & fees
15 Sept - 16 Sept
Game Room + Bar Lounge, 35 Min to Boston
Exterior

10. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (4 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is NZ$443
includes taxes & fees
20 Sept - 21 Sept
Cottage by the Castle – Downtown Spencer
Room

11. Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.4 out of 10, Exceptional, (36 reviews)
"Lovely and great location "
United States
Kimberlee K.
The price is NZ$490
includes taxes & fees
21 Sept - 22 Sept
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Living area

12. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is NZ$1,008
includes taxes & fees
15 Sept - 16 Sept
6 Beds Home w/Game Room Perfect for Groups
Private kitchen

13. Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat
Killingly
7.4 out of 10, Good, (3 reviews)
"Great setup. Perfect crash pad for a weekend of the Natchaug Epic bike race in Thompson… slept 8 no problem. Host was helpful and beds were clean, kitchens were just what we needed"
United States
shawn c b.
Mohegan Sun Getaway Large Group Retreat
Outdoor dining

14. Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (24 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
The price is NZ$543
includes taxes & fees
24 Sept - 25 Sept
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Interior

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (23 reviews)
"We really appreciated the kindling and firewood for the outdoor fire pit.The house was clean and nice."
United States
Christian C.
The price is NZ$1,483
includes taxes & fees
14 Sept - 15 Sept
Lake House in Sturbridge w/All the Views!
Interior

16. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (6 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 NZ$524
includes taxes & fees
16 Sept - 17 Sept
Spacious, unique barn with beautiful views.
Room

17. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.0 out of 10, Very good, (5 reviews)
The price is NZ$925
includes taxes & fees
14 Sept - 15 Sept
Clifford Luxury Retreat 3BR Self Check In Home
Living area

18. 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 NZ$2,894
includes taxes & fees
18 Sept - 19 Sept
Sleeps 15 • Pool • Retreat
Property grounds

19. Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
The price is NZ$1,378
includes taxes & fees
6 Oct - 7 Oct
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Private kitchen

20. 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, (1 review)
"The house was located in a quiet, nice, pleasant, neighborhood. The rooms were spacious and comfortable. The house was very clean and the beds were comfortable. The house was located near all kinds of stores, pharmacy’s, and good restaurants. I’d I had to make a negative comment it would be that all the bedrooms were on the second floor which was tough for two of our party. The property owner was quick to respond to questions we had. Overall, a very pleasant stay."
United States
Samantha R.
The price is NZ$974
includes taxes & fees
14 Sept - 15 Sept
4-bedroom house in nice Holden with WiFi, AC
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

Spark by Hilton Milford Boston

Spark by Hilton Milford Boston

10/10 Excellent
"Great staff…Dimple was very helpful. Room was spotless and appeared to recently upgraded. Much improved on previous Best Western brand."
Robert 1-night trip
Posted less than an hour ago
Spark by Hilton Milford Boston

Find out more about Webster

Webster Holiday Homes information

Number of reviews
345
Accommodation
108 Holiday Homes
Lowest Price
NZ$323
Highest Price
NZ$2,894