Webster Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Webster

Wrecked at Ron’s

10.0 out of 10, Exceptional, (10)
"My family thoroughly enjoyed our accomadations. Ron was attentive and quick to respond to our needs, gave a great house tour, and was proactive in offering assistance. "
Wrecked at Ron’s

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

The price is NZ$771
includes taxes & fees
8 Oct - 9 Oct
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

Webster Lake - One Home -Two Apartments

10.0 out of 10, Exceptional, (16)
"The house was better than we expected. We had a 16month old and there was a brand new pack and play for us to use. The house was clean, organized and ready for our family. We had 9 adults and 1 toddler and there was plenty of room to accommodate us all. The owners were VERY responsive to all our inquiries. We would definitely recommend this property!"
Webster Lake - One Home -Two Apartments

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

9.6 out of 10, Exceptional, (5)
"We had a great time. The house was beautiful. Well kept and ready for us. The hosts were amazing. Any concerns or questions were answered quickly. Thank you."
The price is NZ$550
includes taxes & fees
6 Oct - 7 Oct
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Dove Cabin up in the Trees

9.8 out of 10, Exceptional, (23)
"This is the sweetest property to stay in when visiting Brimfield market. I highly suggest any of the cabins on the property "
The price is NZ$443
includes taxes & fees
1 Oct - 2 Oct
Dove Cabin up in the Trees

Brimfield Waterfront cottage

10.0 out of 10, Exceptional, (9)
"Property is in excellent condition, just the right amount of space for us. "
Brimfield Waterfront cottage

Amazing lake house with everything you need!

9.8 out of 10, Exceptional, (17)
"Great time, lovely location, easy to access and beautiful lake!"
Amazing lake house with everything you need!

The Tree House at Underhill Hollow

9.4 out of 10, Exceptional, (32)
"My 10 year old loved this stay! Meeting the goats and sheep was fun and it was located in a nice area. Would love to visit again!"
The price is NZ$300
includes taxes & fees
28 Sept - 29 Sept
The Tree House at Underhill Hollow

Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

10.0 out of 10, Exceptional, (132)
"It was our 4 lake vacation there. We absolutely love it and our dog Charlie enjoys the beautiful yard and and a swim in a little bay at this property."
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

Wizard's Roost at Underhill Hollow

9.6 out of 10, Exceptional, (17)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
The price is NZ$272
includes taxes & fees
28 Sept - 29 Sept
Wizard's Roost at Underhill Hollow

Spacious 4-bedroom house in charming Worcester with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (20)
"Great space to hang out with family while in town. "
Spacious 4-bedroom house in charming Worcester with AC, WiFi

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

9.0 out of 10, Wonderful, (7)
"Only issue with the location is exiting the property directly to a busy street. Nice safe, beautiful neighborhood."
The price is NZ$364
includes taxes & fees
29 Sept - 30 Sept
Beautiful family getaway, walking distance to markets, 35 min drive to Boston

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

9.8 out of 10, Exceptional, (39)
"WE enjoyed our stay."
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Spacious 2 Bedroom 1 Bath apt

10.0 out of 10, Exceptional, (1)
"Great host and excellent apartment "
The price is NZ$559
includes taxes & fees
13 Oct - 14 Oct
Spacious 2 Bedroom 1 Bath apt

Secluded 2-Acre Lakefront Home! Book Your Getaway!

9.8 out of 10, Exceptional, (73)
"We enjoyed our stay, especially sitting on the deck and listening to the birds. We would definitely love to return again sometime."
The price is NZ$1,015
includes taxes & fees
29 Sept - 30 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Newly updated/furnished 3 bedrooms house

8.6 out of 10, Excellent, (11)
"The house was very clean when we arrived. Lovely kitchen/dining area. We cooked full meals and only had to buy minimal things. Bedrooms were spacious and comfortable. I would definitely recommend this place and/or stay again if needed!"
Newly updated/furnished 3 bedrooms house

Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

9.8 out of 10, Exceptional, (114)
"The weather didn’t cooperate enough for us to enjoy the water, but it was lovely to look at"
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

Spacious 4-bedroom with four and half bathrooms

10.0 out of 10, Exceptional, (4)
"We needed a place to stay while our hardwood floors were being refinished and this was perfect. We have a dog and 2 cats and there was plenty of space. The house was clean and as advertised."
The price is NZ$862
includes taxes & fees
29 Sept - 30 Sept
Spacious 4-bedroom with four and half bathrooms

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

9.6 out of 10, Exceptional, (25)
"I stayed at this property for almost a month and thoroughly enjoyed it. It had everything I needed and is conveniently located to Route 9 and I-435. The host was very responsive, which I greatly appreciated. It's nice to know such a comfortable place is available in Shrewsbury."
The price is NZ$459
includes taxes & fees
7 Oct - 8 Oct
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Charming single family Cottage, pet friendly w fenced in yard,

2.0 star property
10.0 out of 10, Exceptional, (16)
"I stayed with my dog for 1 night and the listing was just as described. "
The price is NZ$341
includes taxes & fees
29 Sept - 30 Sept
Charming single family Cottage, pet friendly w fenced in yard,
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Webster Hotel Reviews

Find out more about Webster

Find out more about Webster

Everything you need to know about Webster holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Webster holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Webster holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Webster holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Webster holiday rentals we have selected for you start as low as NZ$272 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Webster rentals

At Expedia, we put the best Webster holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Webster?

Yes, there are holiday rentals in Webster close to Mohegan Bowl, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Webster has to offer?

Webster Lake - One Home -Two Apartments: This highly rated holiday home rental in Webster is located on a lake, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Webster?

Expedia has 5 holiday rentals for your stay in Webster.

What can I see and do in Webster?

Lake Webster and Lake Chaubunagungamaug are a couple of scenic spots to enjoy the outdoors, whereas Indian Ranch is one of the cultural attractions. Mohegan Bowl and Buffumville Lake are a couple of places you'll find in the wider area.

What are holiday rentals like in Webster?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Webster. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.