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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Webster vacation rentals

A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

1. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (46 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
$163 nightly
The price is $186
Nov 8 - Nov 9
Total with taxes and fees
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

2. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!!"
United States
Elizabeth G.
$158 nightly
The price is $180
Nov 8 - Nov 9
Total with taxes and fees
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.

3. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
$158 nightly
The price is $180
Nov 8 - Nov 9
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.

4. 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.
$323 nightly
The price is $368
Nov 8 - Nov 9
Total with taxes and fees
Rustic Farmette Studio with Hot Tub & Pool
A two-story house with a front porch, stone steps, and a driveway.

5. 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.
$169 nightly
The price is $194
Nov 17 - Nov 18
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Dining Room

6. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
10.0 out of 10, Exceptional, (4 reviews)
"Offers good value with cozy accommodations."
United States
Anonymous traveler
$88 nightly
The price is $101
Nov 8 - Nov 9
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (95 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
$543 nightly
The price is $618
Nov 7 - Nov 8
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

8. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (4 reviews)
"Gorgeously decorated and ultra-clean. Was the perfect rental for my sisters wedding at Salem Cross Inn"
United States
Trish N.
$272 nightly
The price is $304
Nov 29 - Nov 30
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
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.
$111 nightly
The price is $124
Nov 8 - Nov 9
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A house with a white porch, a black door, and a window with a white frame.

10. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.2 out of 10, Wonderful, (5 reviews)
"I had a lovely stay at the cottage! It was clean, comfortable, and quiet with a great view. The hosts were very helpful."
United States
Aaron H.
$232 nightly
The price is $264
Nov 8 - Nov 9
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
A lakeside cabin with a deck, a dock, and a small docked boat.

11. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
9.8 out of 10, Exceptional, (98 reviews)
"very clean, wonderful location"
United States
Anonymous traveler
$406 nightly
The price is $454
Nov 9 - Nov 10
Total with taxes and fees
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A wooden cabin with a glass upper floor, surrounded by a forest.

12. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful cabin wishing it was a waterfront"
United States
Magdalena W.
$233 nightly
The price is $246
Nov 7 - Nov 8
Total with taxes and fees
Dove Cabin up in the Trees
A modern living room with a flat-screen TV, a sofa, and two armchairs. There is a dining area with a kitchen in the background.

13. 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.
$369 nightly
The price is $390
Nov 8 - Nov 9
Total with taxes and fees
12B-Cozy 3BR Apartment with Koi Pond in Worcester
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

14. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.6 out of 10, Excellent, (7 reviews)
"We loved our stay here. The home and the host were both exceptional. We highly recommend this home!"
United States
Martin G.
$417 nightly
The price is $441
Nov 9 - Nov 10
Total with taxes and fees
Clifford Luxury Retreat 3BR Self Check In Home
Living area

15. 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.
$309 nightly
The price is $354
Nov 9 - Nov 10
Total with taxes and fees
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A spacious room with large windows, a wooden dining table with chairs, and a view of the outdoors.

16. 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.
$223 nightly
The price is $237
Nov 9 - Nov 10
Total with taxes and fees
Zen Inspired Retreat with Private Forest Trails
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

17. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean location to stay."
United States
Mike O.
$426 nightly
The price is $488
Nov 8 - Nov 9
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

18. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
9.0 out of 10, Wonderful, (2 reviews)
"Nice and very clean. Host communicated fast and helpful."
United States
Ekaterina
$92 nightly
The price is $105
Nov 8 - Nov 9
Total with taxes and fees
Clean & Cozy Private-3 floor_R 2
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
8.8 out of 10, Excellent, (3 reviews)
"Rented the property to attend a series of events at Clark University. Literally walking distance to the school so it was quite convenient. Apartment was clean, beds were comfortable. Being able to park three cars in the driveway was a huge plus as street parking near the apartment was extremely challenging. Being a Clark alum, was quite familiar with the neighborhood so I knew what to expect. Felt completely safe in the apartment as every door to the hallways had sufficient locks. We did blow a...
United States
Elyse D.
$255 nightly
The price is $292
Nov 9 - Nov 10
Total with taxes and fees
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
The Cottage is nestled next to the historic Sagendorph Mansion.

20. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (9 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
$222 nightly
The price is $223
Nov 8 - Nov 9
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
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

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent
"We love this hotel, for the beauty of its grounds, the cleanliness of its rooms,its pet friendliness and its dining room that serves New England classic dishes, even Indian pudding."
Carolyn 2-night trip
Posted 3 hours ago
Publick House Historic Inn and Country Motor Lodge

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 $105 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.