Lake Chaubunagungamaug aka Webster Lake in spring in town of Webster, Massachusetts MA, USA. The original name Lake is the longest name in US.

Holiday Homes in Webster

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Check prices for these dates

In two weeks
3 July - 5 July
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

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 AU$529
includes taxes & fees
26 June - 27 June
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 AU$1,013
includes taxes & fees
26 June - 27 June
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (37 reviews)
"Such a fun getaway!"
United States
Patrice D.
The price is AU$278
includes taxes & fees
18 June - 19 June
The Tree House at Underhill Hollow
Bathroom

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

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.6 out of 10, Exceptional, (32 reviews)
"Lovely and great location "
United States
Kimberlee K.
The price is AU$446
includes taxes & fees
21 June - 22 June
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
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 AU$373
includes taxes & fees
16 June - 17 June
Angel Sky Challenge
Smart TV

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.6 out of 10, Exceptional, (47 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
The price is AU$495
includes taxes & fees
22 June - 23 June
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (3 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 AU$378
includes taxes & fees
17 June - 18 June
Spacious, unique barn with beautiful views.
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (22 reviews)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
The price is AU$269
includes taxes & fees
21 June - 22 June
Wizard's Roost 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, (14 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AU$269
includes taxes & fees
18 June - 19 June
SteamPunk Bunk House and Intergalactic Way Station
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, (21 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 AU$526
includes taxes & fees
23 June - 24 June
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
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, (1 review)
"The only thing missing was a BBQ"
United States
Charmen B.
Cozy 3-bedroom house in serene Worcester with fitness room and office
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, (1 review)
"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 AU$629
includes taxes & fees
8 July - 9 July
Beautiful Worcester Downtown King Bd/Office World Cup Boston
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, (5 reviews)
"This is a nice place for solo travelers or a small family with kids. The kid’s bedroom has tons of games and is themed nicely. The backyard is huge but unfenced and the property is off of a busy road. Th house itself was clean and the host offered a variety of things such as slippers for the whole family, house shoes, and bath things for everyone. The house does not have a tv but the wifi works well. "
United States
Chantay-Rose
The price is AU$372
includes taxes & fees
16 June - 17 June
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Fridge, microwave, oven, coffee/tea maker

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.
The price is AU$1,145
includes taxes & fees
12 July - 13 July
Mohegan Sun Getaway Large Group Retreat
Fridge, microwave, oven, stovetop

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)
"10/10 great place to stay"
United States
Tyler B.
The price is AU$719
includes taxes & fees
22 June - 23 June
Spacious 4-bedroom with four and half bathrooms
Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (25 reviews)
"Welcoming host! Beautiful house with great amenities!"
United States
maria c.
The price is AU$960
includes taxes & fees
16 June - 17 June
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
The price is AU$609
includes taxes & fees
17 June - 18 June
Clifford Luxury Retreat 3BR Self Check In Home
TV, fireplace

Sleeps 15 • Pool • World Cup 2026 • Retreat

Sleeps 15 • Pool • World Cup 2026 • Retreat
Brimfield
10.0 out of 10, Exceptional, (34 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 AU$2,476
includes taxes & fees
19 June - 20 June
Sleeps 15 • Pool • World Cup 2026 • Retreat
Private kitchen

4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
The price is AU$794
includes taxes & fees
29 June - 30 June
4-bedroom house in nice Holden with WiFi, AC
Dining

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (84 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is AU$1,118
includes taxes & fees
27 June - 28 June
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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 Boston - Milford by IHG

Holiday Inn Express Boston - Milford by IHG

10/10 Excellent
"Great place to stay conveniently located. Also want to mention that the 24 hour front desk service is beyond exceptional especially the overnight girl Ella who is constantly making sure that all guests have what they need or if they need anything during the night she’s always there with a smile on her face. Look forward to my next return."
scotty 4-night trip
Posted less than an hour ago
Holiday Inn Express Boston - Milford by IHG

Find out more about Webster

Webster Holiday Homes information

Number of reviews
350
Accommodation
101 Holiday Homes
Lowest Price
AU$269
Highest Price
AU$2,476