A calm lake surrounded by trees and a clear sky.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Webster vacation homes

A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

1. Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Webster
9.6 out of 10, Exceptional, (5 reviews)
"Owner was easy to communicate with. Cute and cozy unit that meet all of our needs for our trip."
United States
Rachele T.
The price is ￥79,155
￥99,734 total
includes taxes & fees
Oct 14 - Oct 15
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

2. Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Webster
10.0 out of 10, Exceptional, (3 reviews)
"We loved the space, it accommodated our larger group and had all the amenities we needed. We only stayed 1 night but would have loved to stay longer! The porch area was very nice to sit out on at night."
United States
Kyle C.
The price is ￥110,817
￥139,520 total
includes taxes & fees
Oct 14 - Oct 15
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

3. 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 ￥19,895
￥30,577 total
includes taxes & fees
Oct 13 - Oct 14
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

4. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 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 ￥19,895
￥29,669 total
includes taxes & fees
Oct 13 - Oct 14
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.

5. 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 ￥19,895
￥29,669 total
includes taxes & fees
Oct 13 - Oct 14
SteamPunk Bunk House and Intergalactic Way Station
A dining area with a high ceiling, skylights, and a view of the outdoors.

6. 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)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is ￥59,366
￥100,843 total
includes taxes & fees
Nov 1 - Nov 2
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

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)
"10/10 great place to stay"
United States
Tyler B.
The price is ￥43,423
￥81,144 total
includes taxes & fees
Oct 19 - Oct 20
Spacious 4-bedroom with four and half bathrooms
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 ￥71,240
￥85,508 total
includes taxes & fees
Oct 12 - Oct 13
Clifford Luxury Retreat 3BR Self Check In Home
A hotel with a central building, outdoor seating area, and a covered patio.

9. 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 traveler
The price is ￥43,535
￥84,704 total
includes taxes & fees
Nov 2 - Nov 3
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

10. 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 ￥34,828
￥69,938 total
includes taxes & fees
Oct 31 - Nov 1
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

11. 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 ￥25,330
￥41,492 total
includes taxes & fees
Oct 11 - Oct 12
Angel Sky Challenge
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

12. 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 ￥47,493
￥132,724 total
includes taxes & fees
Oct 12 - Oct 13
Lake House in Sturbridge w/All the Views!
A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

13. 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 ￥26,485
￥33,937 total
includes taxes & fees
Oct 13 - Oct 14
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
The Cottage is nestled next to the historic Sagendorph Mansion.

14. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (8 reviews)
"The cottage is beautiful, cozy and super comfortable! We loved it! The hosts also were super, communicative and friendly. The place was clean, we had everything we needed, is in a very safe area, and very pretty! Hight recommended! Thank you for hosting us!"
United States
Fabiola
The price is ￥36,135
￥41,475 total
includes taxes & fees
Oct 12 - Oct 13
Cottage by the Castle – Downtown Spencer
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
9.2 out of 10, Wonderful, (10 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 ￥26,644
￥33,651 total
includes taxes & fees
Oct 13 - Oct 14
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A stone wall, a metal gate, and a building with a blue door and a number '74' sign.

16. A Timeless Retreat at Historic Crompton House

A Timeless Retreat at Historic Crompton House
Elm Park
10.0 out of 10, Exceptional, (1 review)
"This is a beautiful property! Great location and amazing hosts! We had everything we needed and were very comfortable. I highly recommend this place!"
United States
Jessica H.
The price is ￥31,187
￥79,722 total
includes taxes & fees
Oct 12 - Oct 13
A Timeless Retreat at Historic Crompton House
A staircase with wooden steps and black balusters, a potted plant on a side table, and a framed floral artwork on the wall.

17. 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 ￥56,992
￥78,454 total
includes taxes & fees
Oct 18 - Oct 19
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
A window with a view of a grassy field and trees.

18. 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 ￥31,264
￥48,112 total
includes taxes & fees
Oct 13 - Oct 14
Spacious, unique barn with beautiful views.
A living room with a sofa, a clock, a floor lamp, and a rug.

19. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (55 reviews)
"Easy in and out. Place was dated but clean. The host was welcoming and easy to work with. Parking is good. A little pricy but safe neighborhood."
United States
Thomas M.
The price is ￥25,504
￥47,409 total
includes taxes & fees
Oct 13 - Oct 14
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

20. 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 ￥156,321
￥280,083 total
includes taxes & fees
Oct 21 - Oct 22
Sleeps 15 • Pool • Retreat
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 Northborough

Spark By Hilton Northborough

8/10 Good
"Overall our stay went well. Biggest complaint in the breakfast included in the price it was minimal with no hot options. It's barely a continental breakfast smh"
Jennifer 1-night trip
Posted 1 hour ago
Spark By Hilton Northborough

Find out more about Webster

Webster Vacation Homes information

Number of reviews
462
Accommodation
108 Vacation Homes
Lowest Price
￥29,669
Highest Price
￥280,083