A calm lake surrounded by trees and a clear sky.

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Webster vacation homes

Property grounds

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

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

3. 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 AED 463
AED 711 total
includes taxes & fees
5 Oct - 6 Oct
The Tree House at Underhill Hollow
Exterior

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 AED 463
AED 690 total
includes taxes & fees
27 Sep - 28 Sep
Wizard's Roost at Underhill Hollow
Property grounds

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 AED 463
AED 690 total
includes taxes & fees
27 Sep - 28 Sep
SteamPunk Bunk House and Intergalactic Way Station
Exterior

6. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (7 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 AED 757
AED 861 total
includes taxes & fees
28 Sep - 29 Sep
Cottage by the Castle – Downtown Spencer
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (25 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 AED 594
AED 1,234 total
includes taxes & fees
28 Sep - 29 Sep
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
2 bedrooms, WiFi (free)

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

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.6 out of 10, Exceptional, (37 reviews)
"Lovely and great location "
United States
Kimberlee K.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Coffee/tea maker, fridge, microwave, oven

9. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (21 reviews)
The price is AED 1,010
AED 1,875 total
includes taxes & fees
27 Sep - 28 Sep
Spacious 4-bedroom with four and half bathrooms
Interior

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

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is AED 790
AED 988 total
includes taxes & fees
1 Oct - 2 Oct
Game Room + Bar Lounge, 35 Min to Boston
Coffee/tea maker, fridge, microwave, oven

11. Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat
Killingly
7.4 out of 10, Good, (3 reviews)
The price is AED 782
AED 2,280 total
includes taxes & fees
28 Sep - 29 Sep
Mohegan Sun Getaway Large Group Retreat
TV

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

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is AED 861
AED 2,386 total
includes taxes & fees
28 Sep - 29 Sep
6 Beds Home w/Game Room Perfect for Groups
Smart TV

13. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (54 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
The price is AED 592
AED 1,092 total
includes taxes & fees
13 Oct - 14 Oct
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Property grounds

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, (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 AED 582
AED 711 total
includes taxes & fees
28 Sep - 29 Sep
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Interior

15. 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 AED 588
AED 950 total
includes taxes & fees
25 Sep - 26 Sep
Angel Sky Challenge
3 bedrooms, desk, iron/ironing board, WiFi (free)

16. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.4 out of 10, Very good, (6 reviews)
The price is AED 1,653
AED 1,972 total
includes taxes & fees
27 Sep - 28 Sep
Clifford Luxury Retreat 3BR Self Check In Home
Dining

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (92 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is AED 1,745
AED 2,839 total
includes taxes & fees
27 Sep - 28 Sep
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Interior

18. 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 AED 727
AED 1,104 total
includes taxes & fees
27 Sep - 28 Sep
Spacious, unique barn with beautiful views.
Dining

19. Luxury Home - Fire Pit - Beach Grill - 2 Decks

Luxury Home - Fire Pit - Beach Grill - 2 Decks
Smithfield
10.0 out of 10, Exceptional, (21 reviews)
"Very nice property. Great host. We left an air mattress as our appreciation. Thank you"
United States
cynthia P.
Luxury Home - Fire Pit - Beach Grill - 2 Decks
Interior

20. 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 AED 1,065
AED 2,933 total
includes taxes & fees
27 Sep - 28 Sep
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

La Quinta Inn by Wyndham Auburn Worcester

La Quinta Inn by Wyndham Auburn Worcester

8/10 Good
"Room was fine but the pillows were uncomfortable. The location was convenient."
Janet 1-night trip
Posted less than an hour ago
La Quinta Inn by Wyndham Auburn Worcester