A calm lake surrounded by trees and a clear sky.

Webster Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Webster vacation rentals

Interior

1. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
$171 nightly
The price is $194
Aug 7 - Aug 8
Total with taxes and fees
The Tree House at Underhill Hollow
Property grounds

2. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
$166 nightly
The price is $188
Aug 9 - Aug 10
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
Exterior

3. 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 10 - Aug 11
Total with taxes and fees
Wizard's Roost at Underhill Hollow
Interior

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$124 nightly
The price is $139
Aug 10 - Aug 11
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Exterior

5. 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, (5 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.
$216 nightly
The price is $245
Sep 1 - Sep 2
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Exterior

6. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (33 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
$244 nightly
The price is $257
Aug 9 - Aug 10
Total with taxes and fees
Dove Cabin up in the Trees
Living area

7. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
$88 nightly
The price is $101
Aug 9 - Aug 10
Total with taxes and fees
Clean & Cozy Private- 3 floor_R 4
Exterior

8. The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (33 reviews)
"Just as advertised clean and comfortable, thank you gentlemen. Keep up the good work. :)"
United States
Herbert
The Carriage House at Chaprae Hall
Exterior detail

9. 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.
$277 nightly
The price is $314
Aug 8 - Aug 9
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
Smart TV

10. 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.
$384 nightly
The price is $440
Aug 9 - Aug 10
Total with taxes and fees
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Interior

11. 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
10.0 out of 10, Exceptional, (1 review)
$354 nightly
The price is $405
Aug 12 - Aug 13
Total with taxes and fees
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Dining

12. Spacious King Bed Near Downtown Worcester with Patio

Spacious King Bed Near Downtown Worcester with Patio
Worcester
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay! And Dave was an awesome host!"
United States
Beth
Spacious King Bed Near Downtown Worcester with Patio
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, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
$200 nightly
The price is $224
Aug 9 - Aug 10
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Exterior detail

14. Quintessential New England Home w/ Patio & Grill!

Quintessential New England Home w/ Patio & Grill!
Putnam
10.0 out of 10, Exceptional, (8 reviews)
"A perfect place to bring our family together to celebrate our parents’ 50th anniversary! The house had everything we needed, was beautifully decorated and thoughtfully furnished, and felt warm and welcoming from the moment we arrived. A truly special stay."
United States
Laurie and Dan C.
$802 nightly
The price is $908
Aug 9 - Aug 10
Total with taxes and fees
Quintessential New England Home w/ Patio & Grill!
TV

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

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (4 reviews)
"It was a great place for my family and i"
United States
Taisha M.
$239 nightly
The price is $274
Aug 11 - Aug 12
Total with taxes and fees
Large 3BD 1st Floor Apartment Minutes from 290
Exterior

16. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (3 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
$259 nightly
The price is $261
Aug 9 - Aug 10
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
Terrace/patio

17. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"Great experience. Thank you "
United States
edmund d.
$657 nightly
The price is $743
Aug 7 - Aug 8
Total with taxes and fees
Stunning Lakefront Escape! Book Your Dream Getaway!
Interior

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

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
8.0 out of 10, Very Good, (1 review)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
$95 nightly
The price is $106
Aug 11 - Aug 12
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
House (5 Bedrooms) | Interior

19. Quintessential New England Home w/ Patio & Grill!

Quintessential New England Home w/ Patio & Grill!
3.0 star property
Putnam
$787 nightly
The price is $905
Aug 9 - Aug 10
Total with taxes and fees
Quintessential New England Home w/ Patio & Grill!
Dining

20. Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (15 reviews)
"Very comfortable and relaxing on the inside with beautiful surroundings and hiking trails right on the property. Exactly what we wanted for a get-away and such close proximity to the zoo where we attended a wedding."
United States
Tammie K.
$248 nightly
The price is $264
Aug 25 - Aug 26
Total with taxes and fees
Zen Inspired Retreat with Private Forest Trails
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Webster Hotel Reviews

Spark By Hilton Northborough

Spark By Hilton Northborough

10/10 Excellent
"Nice hotel , great atmosphere, friendly staff"
Calvin 2-night trip
Posted less than an hour ago
Spark By Hilton Northborough

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 $106 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.