Webster Holiday Rentals

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Holiday Rentals in Webster

Secluded 2-acre Lake Front Home! Special off-season rates!
9.8 out of 10, Exceptional, 52 reviews
"The property is stunning and just as described - large, clean, beautiful, spacious, and RIGHT on the lake. Heather was super responsive and friendly!"
The price is NZ$1,305
per night
5 Jun - 6 Jun
Secluded 2-acre Lake Front Home! Special off-season rates!
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
10.0 out of 10, Exceptional, 165 reviews
"This was our third time staying, and definately won’t be our last!"
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
Lakefront | King | PetsOK | W&D | Fire Pit | Kayak
9.6 out of 10, Exceptional, 8 reviews
"Clean comfortable cottage in a beautiful location. Kitchen and bathroom are well stocked with all the essentials. Would definitely stay here again!"
The price is NZ$627
per night
5 Jun - 6 Jun
Lakefront | King | PetsOK | W&D | Fire Pit | Kayak
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Cozy 2-Floor Apartment with Garage Access
9.6 out of 10, Exceptional, 8 reviews
"The place was cozy and comfortable and communication with the host was smooth! Would stay again!"
Cozy 2-Floor Apartment with Garage Access
Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!
10.0 out of 10, Exceptional, 73 reviews
"The pictures don't do this location justice. It was the most beautiful location i would love to spend more time here.The hosts were awesome leaving us drinks in the fridge even. Thank you so much. I will come back."
Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!
One Bedroom Queen Suite with sofa bed and fully equipped kitchen
6.0 out of 10, 1 review
"Put my and my family of 5 in the wrong room, which they easily changed to a 2x2 as i had rented. Sunday afternoon the "maintence" man let himself in as we are in the room letting our dog outside. He didnt speak much english. Not sure what he was doing but he looked in our electric oven and than left. We didnt feel real safe so when we left we made sure to tske any valubles out and rigged the room to see of people had come in again. "
The price is NZ$257
per night
29 Jun - 30 Jun
One Bedroom Queen Suite with sofa bed and fully equipped kitchen
One Bedroom Fully Furnished Apartment
9.6 out of 10, Exceptional, 8 reviews
"The apartment we extremely clean and tidy. Had all amenities one would need. They even had bottles of water and snacks. Would recommend staying here!"
One Bedroom Fully Furnished Apartment
Spacious Massachusetts Apartment #2
9.2 out of 10, Wonderful, 7 reviews
"When I needed to communicate everything was explained to me. The place was very clean. Every thing was exactly as it was listed"
Spacious Massachusetts Apartment #2
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
9.8 out of 10, Exceptional, 24 reviews
"This property was an exvellent location for my daughter's graduation. "
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
The Tree House at Underhill Hollow
10.0 out of 10, Exceptional, 2 reviews
"We enjoyed Underhill Hollow, beautiful spot with whimsy & hospitality."
The price is NZ$302
per night
5 Jun - 6 Jun
The Tree House at Underhill Hollow
Waterfront Pool Sturbridge Village Country Estate
9.8 out of 10, Exceptional, 43 reviews
"We stayed here with our wedding party and it was perfect! The house is well stocked and we were able to have some people over for a welcome dinner. The property and house is stunning and we all had a great time!"
Waterfront Pool Sturbridge Village Country Estate
1x1 Serenity in the Suburbs: Your Ideal Retreat in Westborough - Boston
8.0 out of 10, Very good, 1 review
The price is NZ$273
per night
10 Jun - 11 Jun
1x1 Serenity in the Suburbs: Your Ideal Retreat in Westborough - Boston
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
10.0 out of 10, Exceptional, 73 reviews
"A sweet home with amazing views and access to the lake. The hosts thought of all the things we would need and had a well stocked home. There were plenty of towels, dishes, and games to use. There were spaces to relax and enjoy both inside and out. The yard felt very private even though other people were next door. We had eight people in our group and though I wouldn’t describe the house as large, it did not feel small for our group. We had a wonderful time and would definitely return!"
The price is NZ$1,027
per night
11 Jun - 12 Jun
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Breathtaking Lakefront Property! Cozy house! Special off-season rates!
10.0 out of 10, Exceptional, 5 reviews
"What a wonderful weekend our book club had staying in the beautiful lake front house! So relaxing, and quiet! Great little town with charming little places to enjoy. Our visit to the local winery was so much fun and the gals there told us to check out a local town celebration which we enjoyed going to. I can’t think of one thing that would have made this weekend any better! We would definitely recommend staying here, and look forward to possibly making this a yearly destination."
Breathtaking Lakefront Property! Cozy house! Special off-season rates!
SteamPunk Bunk House and Intergalactic Way Station
10.0 out of 10, Exceptional, 1 review
"The Steampunk house was delightful. A new surprise in every cabinet and room. Accommodations were very comfortable. A couple of suggestions - improve the internet access and TV options. More dishes. But otherwise wonderful."
The price is NZ$292
per night
7 Jun - 8 Jun
SteamPunk Bunk House and Intergalactic Way Station
Full family home 200 ft from the lake shore. Dog friendly!
10.0 out of 10, Exceptional, 1 review
"Loved the lake house! Would stay again."
The price is NZ$943
per night
17 Jun - 18 Jun
Full family home 200 ft from the lake shore. Dog friendly!
Leicester Lake Front Home, Come Relax!
10.0 out of 10, Exceptional, 14 reviews
"Great view. Enjoyed the property. Perfect for seven of us!"
Leicester Lake Front Home, Come Relax!
Cetrl Cozy Lux Renovated 2KB,1QB-w/Parking,Dtwn,6+
Cetrl Cozy Lux Renovated 2KB,1QB-w/Parking,Dtwn,6+
Bucolic Villa: Private Pool, Playground, King Beds
8.6 out of 10, Excellent, 16 reviews
"I booked this listing for a group of friends who traveling through the area to visit the Treehouse Brewery that is 10 minutes away. We wanted a place to relax, enjoy some good food, and take in the area. The house is really charming for an older house. You can tell there has been quite a bit of work done to renovate and that really comes through. However, I found some of the details lacking. You can tell that the cleaning crew that looks after the house missed quite a bit. - Chairs in the...
The price is NZ$1,352
per night
24 Jun - 25 Jun
Bucolic Villa: Private Pool, Playground, King Beds
Luxury Home, Pool, fireplace
10.0 out of 10, Exceptional, 20 reviews
"Picked this location because it was on the route from West Point to Gillette stadium. It was an hour closer for our son (and friends) to get here than if we had stayed in Boston and it put him that closer for drive home on Sunday. The house was great and well decorated for Christmas. My wife’s comment was that she felt like we were in a Hallmark movie. The host was very responsive (not that we needed anything). And Army beat Navy! Great weekend."
Luxury Home, Pool, fireplace
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See all available properties in Webster
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.

Other types of properties in Webster you may be interested in

Wellsworth Hotel
3.0 star property
9.2 out of 10, Wonderful, 1,012 reviews
"Excellent staff. Kid friendly."
The price is NZ$193
per night
1 Jul - 2 Jul
Wellsworth Hotel
Sonesta Select Boston Milford
3.0 star property
8.4 out of 10, Very good, 845 reviews
"Very good property and not too loud neighborhood. A little pricey"
The price is NZ$245
per night
18 Jun - 19 Jun
Sonesta Select Boston Milford
AVIA Residences on Research - Extended Stay
3.0 star property
8.4 out of 10, Very good, 487 reviews
"I liked everything about my stay it was a great place I would definitely recommend it and if I ever come back I’ll stay here "
The price is NZ$226
per night
29 Jun - 30 Jun
AVIA Residences on Research - Extended Stay
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Webster holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Webster. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Webster. Seeing all the best attractions is bound to make you fall in love with Webster. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Webster short-term rentals, that won’t be hard to do.

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?

Secluded 2-acre Lake Front Home! Special off-season rates!: This holiday home rental outside of 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Webster?

Expedia has 3 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.

Recent reviews of Webster properties
Expedia verified reviews