A calm lake surrounded by trees and a clear sky.

Webster Holiday Rentals

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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 holiday rentals

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 HK$3,922
HK$4,661 total
includes taxes & fees
14 Oct - 15 Oct
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 HK$5,491
HK$6,528 total
includes taxes & fees
14 Oct - 15 Oct
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, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is HK$988
HK$1,519 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$988
HK$1,474 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$988
HK$1,474 total
includes taxes & fees
28 Sept - 29 Sept
SteamPunk Bunk House and Intergalactic Way Station
A bedroom with a wooden bed, large windows, and a view of greenery outside.

6. Rustic Farmette Studio with Hot Tub & Pool

Rustic Farmette Studio with Hot Tub & Pool
Thompson
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and quiet location"
United States
Lynn J.
The price is HK$1,961
HK$2,863 total
includes taxes & fees
28 Sept - 29 Sept
Rustic Farmette Studio with Hot Tub & Pool
A two-story house with a front porch, stone steps, and a driveway.

7. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
9.0 out of 10, Wonderful, (8 reviews)
"Clean place, easy check-in and comfortable place. We appreciated the coffee and water, microwave and clean towels. We would stay here again!! Thank you!! "
United States
Lucy L.
The price is HK$974
HK$1,728 total
includes taxes & fees
6 Oct - 7 Oct
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

8. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
The price is HK$628
HK$899 total
includes taxes & fees
29 Sept - 30 Sept
Clean & Cozy Private-3 floor_R 2
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

9. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
6.0 out of 10, (3 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is HK$745
HK$1,008 total
includes taxes & fees
28 Sept - 29 Sept
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A wooden cabin with a glass upper floor, surrounded by a forest.

10. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is HK$1,377
HK$1,953 total
includes taxes & fees
28 Sept - 29 Sept
Dove Cabin up in the Trees
A bedroom with a bed, a bedside table with a lamp, a window with curtains, a painting on the wall, and a carpet with a geometric pattern.

11. Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat

Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Holland
10.0 out of 10, Exceptional, (1 review)
"Cute place! Susan was a great host and the cabin was perfect for a qick getaway weekend and some reconnection with mother nature.."
United States
Jessica K.
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
A house with a white porch, a black door, and a window with a white frame.

12. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.0 out of 10, Wonderful, (4 reviews)
"Great spot, clean and cozy."
United States
Bud n' Mary's Marina B.
The price is HK$1,922
HK$2,367 total
includes taxes & fees
28 Sept - 29 Sept
Cozy 1-bedroom cottage in serene Pomfret.
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

13. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is HK$1,592
HK$2,830 total
includes taxes & fees
30 Sept - 1 Oct
Cozy Chic Countryside Haven - Sleeps 4 , Firepit

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 HK$1,616
HK$1,781 total
includes taxes & fees
28 Sept - 29 Sept
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, (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 HK$1,173
HK$1,486 total
includes taxes & fees
28 Sept - 29 Sept
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

16. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is HK$1,000
HK$2,671 total
includes taxes & fees
28 Sept - 29 Sept
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A living room with a gray sofa, a coffee table, and a rug. There are two windows with blinds, a door, and a wall-mounted plant.

17. Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (5 reviews)
"It was a great place for my family and i"
United States
Taisha M.
The price is HK$886
HK$2,047 total
includes taxes & fees
29 Sept - 30 Sept
Large 3BD 1st Floor Apartment Minutes from 290
A small, single-story cabin with a porch and a small deck, surrounded by trees and a lake.

18. Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (40 reviews)
"We had a nice stay in this cabin by the lake. It was close to UCONN so the convenience of the location was wonderful. "
United States
Jennifer P.
The price is HK$1,217
HK$2,459 total
includes taxes & fees
30 Sept - 1 Oct
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

19. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Main South
8.0 out of 10, Very good, (2 reviews)
"The host was very communicative and obviously has tried to make this unit a reasonable place to have people stay. However, the layout of the place was not ideal. They turned a front sitting room into a bedroom, but it doesn't really work well. Further, that room smelled like marijuana our whole stay (1-night). It connected to the stairwell up to the units above, and my guess is that those people just smoke weed all day/night and it's impacting this unit. Further, the outside of the house is...
United States
Jeffrey B.
The price is HK$1,000
HK$2,491 total
includes taxes & fees
28 Sept - 29 Sept
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

20. 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)
"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 HK$1,922
HK$5,694 total
includes taxes & fees
28 Sept - 29 Sept
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

10/10 Excellent
"Could’ve used an update but it was very clean. The staff were super and very helpful. The bed was comfortable and the room was sufficient. Nice breakfast. Close to a lot of restaurants and shopping. I’d stay here again."
Debra 1-night trip
Posted less than an hour ago
La Quinta Inn by Wyndham Auburn Worcester

Find out more about Webster

Search for holiday rentals in Webster on Expedia! You can easily find your home rentals, villas, holiday apartments in Webster using one of the methods below:

  • View our selection of featured holiday rentals in Webster
  • Use the map to find apartments and other holiday homes in the Webster neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Webster while they last

Look no further and take a look at our great range of rental properties in Webster!

Frequently asked questions

Can I find holiday rentals in Webster?

Yes, there are holiday rentals in Webster close to Mohegan Bowl, or you can select a more secluded option if you're looking for a relaxing stay. Webster is known for its lake views and seafood restaurants. Make sure you have time to check out the entertainment choices while you're in the area.

What are some of the best holiday rentals that Webster has to offer?

Webster Lake - One Home -Two Apartments: This highly rated holiday home rental in Webster is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Another good choice for your trip to Webster is 3-bedroom house on Webster Lake with amazing views, beach and boat launch access.

How many holiday rentals will I find in Webster?

Expedia has 5 holiday rentals for your stay in Webster.

What can I see and do in Webster?

Cultural attractions include Indian Ranch, whereas Mohegan Bowl is just one of the family-friendly sights. Lake Chaubunagungamaug and Dudley Hill Golf Club at Nichols College are a couple of places you'll find in the wider area.

What are holiday rentals like in Webster?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Webster. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.