A calm lake surrounded by trees and a clear sky.

Search Holiday Homes in Webster

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Webster holiday homes

A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

1. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (44 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is £151
includes taxes & fees
18 Oct - 19 Oct
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

2. 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 £145
includes taxes & fees
18 Oct - 19 Oct
Wizard's Roost at Underhill Hollow
A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

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 £145
includes taxes & fees
24 Oct - 25 Oct
SteamPunk Bunk House and Intergalactic Way Station
A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (93 reviews)
"Beautiful lake house. The dock with the kayaks and paddle boat made it so much fun for the kids. The dock isnt far from the house but there a decent hill down to it. Totally manageable for most people though. The open house concept kitchen area made it great for everyone to be together."
United States
Amanda S.
The price is £483
includes taxes & fees
2 Nov - 3 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
The Cottage is nestled next to the historic Sagendorph Mansion.

5. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (8 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is £182
includes taxes & fees
18 Oct - 19 Oct
Cottage by the Castle – Downtown Spencer
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

6. 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)
"Very clean and readily met the needs of our family of 7 traveling on vacation from Washington DC to Maine. Would stay again."
United States
Jim O.
The price is £377
includes taxes & fees
21 Oct - 22 Oct
Spacious 4-bedroom with four and half bathrooms
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (24 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 £621
includes taxes & fees
18 Oct - 19 Oct
Lake House in Sturbridge w/All the Views!
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

8. 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)
The price is £400
includes taxes & fees
19 Oct - 20 Oct
Clifford Luxury Retreat 3BR Self Check In Home
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

9. Beautiful two-story home close to downtown worcester 5beds-4bedroom

Beautiful two-story home close to downtown worcester 5beds-4bedroom
Worcester
9.0 out of 10, Wonderful, (20 reviews)
"Great house-clean, great location."
United States
Kathleen R.
The price is £337
includes taxes & fees
31 Oct - 1 Nov
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A hotel with a central building, outdoor seating area, and a covered patio.

10. 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 £398
includes taxes & fees
10 Nov - 11 Nov
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

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

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
The price is £165
includes taxes & fees
17 Oct - 18 Oct
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

12. 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 £197
includes taxes & fees
11 Nov - 12 Nov
Angel Sky Challenge
A staircase with wooden steps and black balusters, a potted plant on a side table, and a framed floral artwork on the wall.

13. Spacious 5-bedroom home with three full bathrooms in charming Worcester location

Spacious 5-bedroom home with three full bathrooms in charming Worcester location
Worcester
The price is £375
includes taxes & fees
27 Oct - 28 Oct
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
A window with a view of a grassy field and trees.

14. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (7 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 £234
includes taxes & fees
22 Oct - 23 Oct
Spacious, unique barn with beautiful views.
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

15. 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
9.4 out of 10, Exceptional, (11 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 £171
includes taxes & fees
20 Oct - 21 Oct
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

16. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (39 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 £1,326
includes taxes & fees
29 Oct - 30 Oct
Sleeps 15 • Pool • Retreat
A two-story residential building with a front porch, a satellite dish, and a small front yard.

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

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
The price is £428
includes taxes & fees
20 Oct - 21 Oct
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

18. 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, (2 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 £426
includes taxes & fees
15 Nov - 16 Nov
4-bedroom house in nice Holden with WiFi, AC
A modern interior with a kitchen, dining area, and living space.

19. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
10.0 out of 10, Exceptional, (1 review)
"Edgar was very responsive and easy to work with. The unit was very clean and well kept. I would definitely stay there again."
United States
debra l.
6 Beds Home w/Game Room Perfect for Groups
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Webster Hotel Reviews

Holiday Inn Express Boston - Milford by IHG

Holiday Inn Express Boston - Milford by IHG

8/10 Good
"Stayed one night for a weekend dog event. Nice clean room with comfortable bed. Hotel front staff was friendly and polite. Good hot breakfast. Very reasonable price with one dog. (Not the norm with other hotels) Would definetly stay again and would recommend. Only issue was bath towel had an odor, hence only 4 stars"
Ann Marie 1-night trip
Posted 5 hours ago
Holiday Inn Express Boston - Milford by IHG

Find out more about Webster

Webster Holiday Homes information

Number of reviews
402
Accommodation
111 Holiday Homes
Lowest Price
£145
Highest Price
£1,326