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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Webster holiday homes

Property grounds

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 €336
includes taxes & fees
26 Jul - 27 Jul
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Property grounds

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 €574
includes taxes & fees
26 Jul - 27 Jul
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Exterior

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 €169
includes taxes & fees
23 Jul - 24 Jul
Wizard's Roost at Underhill Hollow
Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is €174
includes taxes & fees
29 Jul - 30 Jul
The Tree House at Underhill Hollow
Property grounds

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is €169
includes taxes & fees
2 Aug - 3 Aug
SteamPunk Bunk House and Intergalactic Way Station
Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (26 reviews)
"Great experience. Thank you "
United States
edmund d.
The price is €649
includes taxes & fees
23 Jul - 24 Jul
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
10.0 out of 10, Exceptional, (2 reviews)
"I had an amazing stay here and would absolutely recommend this place to anyone visiting Boston or Worcester, Massachusetts. The house was truly 100% excellent. Everything was incredibly clean, spacious, and well organized. I loved the kitchen, my room, and the bathroom, everything was spotless and very comfortable. Honestly, the entire home was sparkling clean and very welcoming.I also slept extremely well during my stay. The bed, pillows, and bedding were so comfortable, which made the...
United States
Masard T.
The price is €346
includes taxes & fees
26 Jul - 27 Jul
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Coffee/tea maker, fridge, microwave, oven

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (12 reviews)
"Perfect location"
United States
Harmony F.
The price is €450
includes taxes & fees
26 Jul - 27 Jul
Spacious 4-bedroom with four and half bathrooms
Interior

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 €233
includes taxes & fees
26 Jul - 27 Jul
Angel Sky Challenge
TV

6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is €617
includes taxes & fees
23 Jul - 24 Jul
6 Beds Home w/Game Room Perfect for Groups
Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.6 out of 10, Exceptional, (5 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 €236
includes taxes & fees
24 Jul - 25 Jul
Spacious, unique barn with beautiful views.
Exterior

Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (2 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is €235
includes taxes & fees
27 Jul - 28 Jul
Cottage by the Castle – Downtown Spencer
Dining

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (87 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is €678
includes taxes & fees
23 Jul - 24 Jul
Secluded 2-Acre Lakefront Home! Book Your Getaway!
3 bedrooms, desk, iron/ironing board, free WiFi

Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
The price is €400
includes taxes & fees
23 Jul - 24 Jul
Clifford Luxury Retreat 3BR Self Check In Home
Property grounds

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, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is €214
includes taxes & fees
12 Aug - 13 Aug
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Coffee/tea maker, fridge, microwave, oven

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
Interior

Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (22 reviews)
"Thank you for a wonderful stay! Our family enjoyed the gorgeous views and the well-equipped home. There were toys, books, and games for the kids, and the beds were very comfortable. We’d definitely stay again!"
United States
Caitlin D.
The price is €807
includes taxes & fees
29 Jul - 30 Jul
Lake House in Sturbridge w/All the Views!
Interior

Cozy 3-bedroom house in serene Worcester with fitness room and office

Cozy 3-bedroom house in serene Worcester with fitness room and office
Worcester
10.0 out of 10, Exceptional, (2 reviews)
"The only thing missing was a BBQ"
United States
Charmen B.
The price is €458
includes taxes & fees
23 Jul - 24 Jul
Cozy 3-bedroom house in serene Worcester with fitness room and office
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (22 reviews)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
The price is €407
includes taxes & fees
18 Aug - 19 Aug
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
TV, fireplace

Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (37 reviews)
"We visited in December, so the pool was closed, but looked inviting even in the snow. The home was so warm and cozy and spacious. We loved our stay."
United States
Gina O.
The price is €1,450
includes taxes & fees
30 Jul - 31 Jul
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

Holiday Inn Express Hotel & Suites Auburn by IHG

Holiday Inn Express Hotel & Suites Auburn by IHG

10/10 Excellent
"This property is in a fairly quiet neighborhood. Some interstate noise. Room was spacious and clean. Bath vanitiy nice and big. Breakfast was very nice with numerous options. There is no coffee maker in the room, but coffee, freshly brewed in lobby 24/7. There is a microwave and refrigerator. There is nice comfortable seating in lobby area and the area around the property was very walkable and safe."
Joyce 1-night trip
Posted 6 hours ago
Holiday Inn Express Hotel & Suites Auburn by IHG

Find out more about Webster

Webster Holiday Homes information

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