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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Webster vacation rentals

Exterior

1. 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.
$166 nightly
The price is $188
Aug 31 - Sep 1
Total with taxes and fees
Wizard's Roost at Underhill Hollow
Interior

2. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (41 reviews)
"Great space, lots of fun."
United States
Douglas C.
$172 nightly
The price is $195
Aug 31 - Sep 1
Total with taxes and fees
The Tree House at Underhill Hollow
Property grounds

3. 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
Aug 31 - Sep 1
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
Exterior detail

4. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (2 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.
$280 nightly
The price is $317
Aug 31 - Sep 1
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
Exterior

5. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (35 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
$247 nightly
The price is $261
Sep 2 - Sep 3
Total with taxes and fees
Dove Cabin up in the Trees
Exterior

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

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.8 out of 10, Excellent, (6 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.
$220 nightly
The price is $249
Sep 22 - Sep 23
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Interior

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

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
7.0 out of 10, Good, (2 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
$72 nightly
The price is $80
Aug 31 - Sep 1
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Terrace/patio

8. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"We loved our stay at this lakeside retreat. We were in town for a wedding and in between family gatherings we were able to relax by the lake. The house was comfortable and well stocked so we didn't have to buy every little thing. I would definitely stay again"
United States
Lisa R.
$656 nightly
The price is $742
Sep 2 - Sep 3
Total with taxes and fees
Stunning Lakefront Escape! Book Your Dream Getaway!
Interior

9. 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.
$285 nightly
The price is $318
Sep 14 - Sep 15
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Private kitchen

10. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (17 reviews)
"Perfect location"
United States
Harmony F.
$452 nightly
The price is $517
Aug 31 - Sep 1
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
Private kitchen

11. FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161

FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161
Worcester
8.0 out of 10, Very Good, (5 reviews)
"Easy in and out when in town. Clean and efficient property. "
United States
Diane S.
$341 nightly
The price is $390
Aug 31 - Sep 1
Total with taxes and fees
FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161
Room

12. 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
$230 nightly
The price is $243
Aug 31 - Sep 1
Total with taxes and fees
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Property grounds

13. 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)
"Excellent communicative host with warm welcome and delightful amenities. Quiet neighborhood with plenty of parking."
United States
Pamela L.
$179 nightly
The price is $199
Sep 1 - Sep 2
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Dining

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (89 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
$685 nightly
The price is $775
Sep 2 - Sep 3
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Dining

15. 12B-Cozy 3BR Apartment with Koi Pond in Worcester

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
9.6 out of 10, Exceptional, (4 reviews)
$410 nightly
The price is $433
Sep 3 - Sep 4
Total with taxes and fees
12B-Cozy 3BR Apartment with Koi Pond in Worcester
Exterior

16. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (4 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
$236 nightly
The price is $238
Aug 31 - Sep 1
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
Living area

17. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (52 reviews)
"Convenient location for our stay. Great communication by host. Bedrooms were spacious and clean. Large driveway for plenty of parking. Convenient to many shopping options and beautiful park close by. "
United States
Theresa L.
$280 nightly
The price is $313
Aug 31 - Sep 1
Total with taxes and fees
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Dining

18. 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.
$246 nightly
The price is $261
Sep 7 - Sep 8
Total with taxes and fees
Zen Inspired Retreat with Private Forest Trails
Room

19. Clean & Cozy Private room - 3 floor_R 1

Clean & Cozy Private room - 3 floor_R 1
Union HIll
2.0 out of 10, (1 review)
$100 nightly
The price is $115
Aug 31 - Sep 1
Total with taxes and fees
Clean & Cozy Private room - 3 floor_R 1
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

Sonesta Select Boston Milford

Sonesta Select Boston Milford

8/10 Good
"This is a good hotel. My wife and I always stay here when we are in the area. Convenience store could be better, tough...no breakfast as well."
ADRIANO 3-night trip
Posted 1 hour ago
Sonesta Select Boston Milford

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 $80 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 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.