Dudley Holiday Rentals

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Holiday Rentals in Dudley

Exterior
Secluded 2-acre Lake Front Home! Special off-season rates!
9.8 out of 10, Exceptional, (51)
"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$1,271
per night
29 May - 30 May
Secluded 2-acre Lake Front Home! Special off-season rates!
Fridge, microwave, oven, stovetop
Cetrl Cozy Lux Renovated 2KB,1QB-w/Parking,Dtwn,6+
Cetrl Cozy Lux Renovated 2KB,1QB-w/Parking,Dtwn,6+
Fridge, microwave, oven, stovetop
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
9.8 out of 10, Exceptional, (24)
"This property was an exvellent location for my daughter's graduation. "
The price is NZ$423
per night
29 May - 30 May
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
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Exterior
The Tree House at Underhill Hollow
10.0 out of 10, Exceptional, (1)
"The tree house stay was so much fun! The treehouse itself was clean, comfortable and very whimsical. The full bathroom was easy to access and very clean. We explored the grounds and competed a treasure hunt where our kids found a gold bar.. and we also found adorable fairy houses hidden throughout the property. The owners were friendly and great with kids. We met the goats, chickens, new puppy, and a baby dragon! We will stay here again when we’re visiting family. Thanks for a great stay. "
The price is NZ$306
per night
27 May - 28 May
The Tree House at Underhill Hollow
Fridge, microwave, oven, stovetop
Lakefront | King | PetsOK | W&D | Fire Pit | Kayak
9.6 out of 10, Exceptional, (8)
"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$764
per night
4 Jun - 5 Jun
Lakefront | King | PetsOK | W&D | Fire Pit | Kayak
Exterior
Full family home 200 ft from the lake shore. Dog friendly!
10.0 out of 10, Exceptional, (1)
"Loved the lake house! Would stay again."
Full family home 200 ft from the lake shore. Dog friendly!
Property grounds
Treehouse | Countryside | Farm Animals | Fire Pit
9.6 out of 10, Exceptional, (17)
"Me and my daughter enjoyed lot."
The price is NZ$619
per night
28 May - 29 May
Treehouse | Countryside | Farm Animals | Fire Pit
Interior
Spacious Massachusetts Apartment #2
9.2 out of 10, Wonderful, (7)
"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
Property grounds
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
10.0 out of 10, Exceptional, (72)
"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$886
per night
29 May - 30 May
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Fridge, microwave, oven, stovetop
Famous Estate now Available to bring the highest scale accommodations to guests!
7.4 out of 10, Good, (9)
"Family gathered from several different states for a large wedding event. We all enjoyed being able to be together in one place. The house wasn’t perfectly spotless and stained carpets and too many things on the walls but nothing terrible. It was all easily overlooked because we were all together with lots of room to spread out if needed."
The price is NZ$1,694
per night
29 May - 30 May
Famous Estate now Available to bring the highest scale accommodations to guests!
Fridge, microwave, oven, stovetop
Waterfront Pool Sturbridge Village Country Estate
9.8 out of 10, Exceptional, (43)
"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
Property grounds
Worcester Home on Indian Lake w/ Shared Boat Dock!
10.0 out of 10, Exceptional, (1)
"Clean and comfy, communication with property manager was quick and informative. Nice lake to relax."
Worcester Home on Indian Lake w/ Shared Boat Dock!
Property grounds
SteamPunk Bunk House and Intergalactic Way Station
10.0 out of 10, Exceptional, (1)
"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$296
per night
27 May - 28 May
SteamPunk Bunk House and Intergalactic Way Station
Fridge, microwave, oven, stovetop
Large 3BR APT w/ enclosed front porch Close to Polar Park, palladium, WPI, DCU
9.8 out of 10, Exceptional, (33)
"I was most appreciative that this place was extremely clean. Sheets smelled nice and the bathroom was clean. This is probably the most important thing to me when I stay at VRBO. Nothing was unexpected. While we did not have much communication with the property manager, the check in process and check out process we’re both smooth. The only challenge that I would mention is that there are a lot of stairs so if you have someone elderly with you, this may be a little bit difficult as the apartment...
Large 3BR APT w/ enclosed front porch Close to Polar Park, palladium, WPI, DCU
Fridge, microwave, oven, stovetop
One Bedroom Fully Furnished Apartment
9.8 out of 10, Exceptional, (7)
"This by far is one of the BEST VRBOs that I've rented! Awesome everything! The check-in process was very simple, the host outlined EVERYTHING, before & during the stay & a notebook provided instructions on literally everything - there isn't anything she did not leave out. The ONLY thing I would say that is it difficult to find, it is upstairs, the stairs are steep, you hear road noise, there weren't any blackout curtains. BUT it was an awesome place to stay & I would go back. Thanks for a great...
One Bedroom Fully Furnished Apartment
Property grounds
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
10.0 out of 10, Exceptional, (164)
"Christine was very welcoming and accommodating with our family and group as we celebrated a college graduation, and two birthdays on her beautiful property. Each room has temperature controls, including the primary bath, and our family felt relaxed throughout our stay."
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
Property grounds
Leicester Lake Front Home, Come Relax!
10.0 out of 10, Exceptional, (13)
"I would highly recommend this place. It was very clean and looks like it was all recently redone. Beautiful sunsets from the back deck in a quiet location. I would highly recommend."
Leicester Lake Front Home, Come Relax!
2 bedrooms, free WiFi
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
9.6 out of 10, Exceptional, (17)
"Overall it was as listed. 2nd floor apt. Only, we did not like floorboards making sound as we walked and there are a few areas where the floor is not even (basic for older homes). Also the blinds were missing a few pieces. But there are curtains for privacy."
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Property grounds
A 123 year old lake property & you won’t believe it! Great fishing spot!
10.0 out of 10, Exceptional, (6)
"Brought son to play for NCDC Boston Jr Bruins"
A 123 year old lake property & you won’t believe it! Great fishing spot!
Property grounds
Bucolic Villa: Private Pool, Playground, King Beds
8.6 out of 10, Excellent, (16)
"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$1,373
per night
28 May - 29 May
Bucolic Villa: Private Pool, Playground, King Beds
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See all available properties in Dudley
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 Dudley you may be interested in

Courtyard
Wellsworth Hotel
3.0 star property
9.2 out of 10, Wonderful, (1005)
"The property was very nice, just no microwave in rooms"
The price is NZ$196
per night
9 Jun - 10 Jun
Wellsworth Hotel
Indoor pool
Sturbridge Host Hotel & Conference Center
3.0 star property
6.6 out of 10, (1005)
"The proerty needs to be renovated, other than thatvwe were happy with out stay."
The price is NZ$247
per night
26 May - 27 May
Sturbridge Host Hotel & Conference Center
Exterior
Hilton Garden Inn Worcester
3.0 star property
8.0 out of 10, Very good, (1000)
"I left something there and CiCi at the desk was so helpful when we called a couple of days later to try to locate it."
The price is NZ$272
per night
27 May - 28 May
Hilton Garden Inn Worcester
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 Dudley 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 Dudley. 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 Dudley. Seeing all the best attractions is bound to make you fall in love with Dudley. 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 Dudley short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Dudley?

Yes, there are holiday rentals in Dudley close to TriState Speedway, or you can select a more secluded option if you're looking for a relaxing stay. Dudley is known for its restaurants.

What are some of the best holiday rentals that Dudley has to offer?

Secluded 2-acre Lake Front Home! Special off-season rates!: This holiday home rental outside of Dudley 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 are there in Dudley?

Choose from 4 Expedia holiday rentals in Dudley for a memorable holiday.

What’s there to see and do in Dudley?

While exploring the area, visit family-friendly sights like TriState Speedway, or get outside and enjoy nature at Lake Webster. Buffumville Lake and Lake Chaubunagungamaug are a couple of places you'll find in the wider area.

What’s a holiday rental in Dudley like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Dudley. Holiday rentals feature amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family getaway.

Recent reviews of Dudley properties
Expedia verified reviews