A calm lake surrounded by trees and a clear sky.

Webster Vacation Rentals

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Webster vacation rentals

Property grounds

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.
$542 nightly
The price is $605
Oct 14 - Oct 15
Total with taxes and fees
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Property grounds

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.
$758 nightly
The price is $847
Oct 14 - Oct 15
Total with taxes and fees
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Exterior

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
Sep 21 - Sep 22
Total with taxes and fees
Wizard's Roost at Underhill Hollow
Interior

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
Sep 21 - Sep 22
Total with taxes and fees
The Tree House at Underhill Hollow
Property grounds

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
Sep 27 - Sep 28
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
Terrace/patio

6. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (28 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.
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (91 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 21 - Sep 22
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Exterior detail

8. 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
Sep 21 - Sep 22
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
Exterior

9. 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
$244 nightly
The price is $257
Sep 21 - Sep 22
Total with taxes and fees
Dove Cabin up in the Trees
Exterior

10. 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.
$192 nightly
The price is $217
Sep 22 - Sep 23
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Living area

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.
$230 nightly
The price is $243
Sep 21 - Sep 22
Total with taxes and fees
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Interior

12. 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.
$115 nightly
The price is $128
Sep 21 - Sep 22
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Interior

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.
$342 nightly
The price is $382
Sep 21 - Sep 22
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Exterior

14. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful stay in the cottage. Great location, and prompt and friendly communication from the owner. Beautifully kept vintage home - such a gem!"
United States
K C.
$259 nightly
The price is $261
Sep 28 - Sep 29
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
Property grounds

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.
$198 nightly
The price is $221
Oct 6 - Oct 7
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
3 bedrooms, desk, iron/ironing board, WiFi (free)

16. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.4 out of 10, Very good, (6 reviews)
$511 nightly
The price is $540
Sep 21 - Sep 22
Total with taxes and fees
Clifford Luxury Retreat 3BR Self Check In Home
Dining

17. 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, (6 reviews)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
$441 nightly
The price is $466
Sep 25 - Sep 26
Total with taxes and fees
12B-Cozy 3BR Apartment with Koi Pond in Worcester
Coffee/tea maker, fridge, microwave, oven

18. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (20 reviews)
"Perfect location"
United States
Harmony F.
$449 nightly
The price is $514
Sep 21 - Sep 22
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
Exterior

19. 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.
$273 nightly
The price is $309
Sep 21 - Sep 22
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Dining

20. 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
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

Holiday Inn Express Hotel & Suites Auburn by IHG

Holiday Inn Express Hotel & Suites Auburn by IHG

10/10 Excellent
"This place is very convenient and clean! I highly recommend it if you’re in the area. Stay Safe and God Bless."
Kathleen 1-night trip
Posted 1 hour ago
Holiday Inn Express Hotel & Suites Auburn by IHG

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 $128 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?

Webster Lake - One Home -Two Apartments: This Webster vacation home rental is located on a lake and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection 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 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.