A calm lake surrounded by trees and a clear sky.

Webster Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Webster vacation 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.
$564 nightly
The price is $630
Oct 14 - Oct 15
Total with taxes and fees
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.
$789 nightly
The price is $881
Oct 14 - Oct 15
Total with taxes and fees
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

3. 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.
$166 nightly
The price is $188
Oct 2 - Oct 3
Total with taxes and fees
Wizard's Roost at Underhill Hollow
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

4. 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.
$171 nightly
The price is $194
Oct 4 - Oct 5
Total with taxes and fees
The Tree House 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.
$166 nightly
The price is $188
Oct 2 - Oct 3
Total with taxes and fees
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.
$305 nightly
The price is $346
Oct 8 - Oct 9
Total with taxes and fees
Rustic Farmette Studio with Hot Tub & Pool
Surroundings [summer] (1-5 km)

7. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
$89 nightly
The price is $102
Oct 2 - Oct 3
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
A two-story house with a front porch, stone steps, and a driveway.

8. 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)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
$194 nightly
The price is $219
Oct 6 - Oct 7
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
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.
$115 nightly
The price is $128
Oct 4 - Oct 5
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

10. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
$100 nightly
The price is $115
Oct 5 - Oct 6
Total with taxes and fees
Clean & Cozy Private-3 floor_R 2
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

11. 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.
$282 nightly
The price is $315
Oct 28 - Oct 29
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
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.
$277 nightly
The price is $314
Oct 14 - Oct 15
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

13. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$122 nightly
The price is $136
Oct 2 - Oct 3
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

14. 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.
$228 nightly
The price is $261
Oct 2 - Oct 3
Total with taxes and fees
Angel Sky Challenge
A dining area with a round table, yellow chairs, a potted plant, and a Buddha painting on the wall.

15. Beautiful family getaway, walking distance to markets, 35 min drive to Boston

Beautiful family getaway, walking distance to markets, 35 min drive to Boston
Hopkinton
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay very nice apartment"
United States
Aaron R.
$190 nightly
The price is $212
Oct 4 - Oct 5
Total with taxes and fees
Beautiful family getaway, walking distance to markets, 35 min drive to Boston
A modern kitchen with stainless steel appliances, wooden ceiling, and a dining area with a wooden table and chairs.

16. Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
Lincoln
10.0 out of 10, Exceptional, (32 reviews)
"Everything was clean and welcoming. Kitchen had everything you need to cook, make coffee, etc. charming and comfortable "
United States
Lindsey D.
$193 nightly
The price is $220
Oct 4 - Oct 5
Total with taxes and fees
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
A spacious room with large windows, a wooden dining table with chairs, and a view of the outdoors.

17. Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely place to stay! This site was meticulously clean, gardens and decor both zen and whimsical, trails well maintained, near a grocery and other shopping. I will stay again!"
United States
Melanie S.
$243 nightly
The price is $258
Oct 5 - Oct 6
Total with taxes and fees
Zen Inspired Retreat with Private Forest Trails
A dining area with a high ceiling, skylights, and a view of the outdoors.

18. 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.
$569 nightly
The price is $644
Nov 1 - Nov 2
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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.
$317 nightly
The price is $363
Oct 4 - Oct 5
Total with taxes and fees
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
A kitchen with wooden cabinets, a window with a view, a vase with flowers, and framed pictures on the windowsill.

20. 12B-Cozy 3BR Apartment with Koi Pond in Worcester

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
9.8 out of 10, Exceptional, (7 reviews)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
$421 nightly
The price is $445
Oct 4 - Oct 5
Total with taxes and fees
12B-Cozy 3BR Apartment with Koi Pond in Worcester
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

Hilton Garden Inn Worcester

Hilton Garden Inn Worcester

10/10 Excellent
"bright and well lit property"
Irena 1-night trip
Posted 8 hours ago
Hilton Garden Inn Worcester

Find out more about Webster

Everything you need to know about Webster vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Webster vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Webster vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Webster vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Webster. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Webster in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $115 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Webster rentals

At Expedia, we put the best Webster vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Webster rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Webster vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Webster. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Webster?

Yes, we have vacation rentals in Webster near Mohegan Bowl, or you can go with a more secluded option if you'd like a relaxing place to 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 vacation rentals in Webster?

3-bedroom house on Webster Lake with amazing views, beach and boat launch access: This Webster vacation home rental is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. Another good choice for your trip to Webster is Webster Lake - One Home -Two Apartments.

How many vacation rentals will I find in Webster?

Expedia has 5 vacation 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 larger area.

What are vacation rentals like in Webster?

Vacation rentals are private properties you can book for a few days or a quick weekend in Webster. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.