Dudley Holiday Rentals

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Holiday Rentals in Dudley

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Woodstock
9.8 out of 10, Exceptional, (75)
"Lovely stay on the lake, we enjoyed the location and the kayaks on the lake. "
United States
Lucy H.
The price is AU$752
includes taxes & fees
8 Dec - 9 Dec
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Bungalow 19 by the lake in Brimfield

2.0 star property
Brimfield
10.0 out of 10, Exceptional, (3)
"Clean, comfortable and great communication with host!"
United States
Elizabeth P.
Bungalow 19 by the lake in Brimfield

Beautiful Lakefront Home with Private Beach

Shrewsbury
9.4 out of 10, Exceptional, (183)
"Peaceful and tranquil. Large space for our family to find alone time and togetherness. Fire pits for smores! And the little beach was so perfect on the quiet lake. "
United States
Ninon R.
Beautiful Lakefront Home with Private Beach

The Tree House at Underhill Hollow

Thompson
9.4 out of 10, Exceptional, (34)
"We had a magical stay! Hosts were accommodating to our needs and eager to make our visit the best."
United States
Grahame E.
The Tree House at Underhill Hollow

Treehouse - Countryside - Farm Animals - Fire Pit

Willington
9.4 out of 10, Exceptional, (28)
"My husband and I were exploring a number of birding hotspots in the quiet corner and decided to try the treehouse. We woke to the dawn bird chorus (without any ambient road noise). Just dreamy!"
United States
Jennifer H.
The price is AU$388
includes taxes & fees
9 Dec - 10 Dec
Treehouse - Countryside - Farm Animals - Fire Pit

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Sturbridge
9.8 out of 10, Exceptional, (89)
"Very Clean, great location"
United States
Anonymous traveller
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Spacious 4-bedroom with four and half bathrooms

Worcester
10.0 out of 10, Exceptional, (5)
"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."
United States
Deb H.
The price is AU$776
includes taxes & fees
8 Dec - 9 Dec
Spacious 4-bedroom with four and half bathrooms

Home Away from Home!

Worcester
9.4 out of 10, Exceptional, (14)
"The property was nice and accommodating for my family! "
United States
Ykeca M.
The price is AU$601
includes taxes & fees
8 Dec - 9 Dec
Home Away from Home!

Wizard's Roost at Underhill Hollow

North Grosvenordale
9.6 out of 10, Exceptional, (21)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
Wizard's Roost at Underhill Hollow

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

Shrewsbury
9.6 out of 10, Exceptional, (32)
"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."
United States
Patty S.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Dove Cabin up in the Trees

Holland
9.8 out of 10, Exceptional, (27)
"Great little getaway - Owners are very friendly and accommodating "
United States
Sharon S.
Dove Cabin up in the Trees

SalsVista 2nd Floor Corner Apt

Forest Grove
10.0 out of 10, Exceptional, (5)
"We very much enjoyed our weekend stay at this place. The apartment was immaculate and very comfortable."
United States
Anonymous traveller
SalsVista 2nd Floor Corner Apt

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

West Brookfield
10.0 out of 10, Exceptional, (15)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
United States
JUNE
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

Amazing lake house with everything you need!

Ashford
9.8 out of 10, Exceptional, (22)
"Great time, lovely location, easy to access and beautiful lake!"
United States
Sam L.
Amazing lake house with everything you need!

SteamPunk Bunk House and Intergalactic Way Station

Thompson
10.0 out of 10, Exceptional, (14)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AU$255
includes taxes & fees
14 Dec - 15 Dec
SteamPunk Bunk House and Intergalactic Way Station

Stunning Lakefront Escape! Book Your Dream Getaway!

Woodstock
10.0 out of 10, Exceptional, (21)
"We had a great stay at the lakehouse. Will definitely consider a future stay."
United States
Savanna
The price is AU$725
includes taxes & fees
8 Dec - 9 Dec
Stunning Lakefront Escape! Book Your Dream Getaway!

Spacious Massachusetts Apartment #2

West Brookfield
9.0 out of 10, Wonderful, (29)
"Really a cute place to stay, very clean and comfortable "
United States
Michelle J.
The price is AU$457
includes taxes & fees
10 Dec - 11 Dec
Spacious Massachusetts Apartment #2

Charming 2-bedroom apartment in welcoming Putnam

Putnam
9.0 out of 10, Wonderful, (2)
"Very nice place. Quiet neighborhood and close to town. "
United States
michael C.
The price is AU$263
includes taxes & fees
15 Dec - 16 Dec
Charming 2-bedroom apartment in welcoming Putnam

Newly updated/furnished 3 bedrooms house

Worcester
8.8 out of 10, Excellent, (13)
"House had everything you needed. Front of house parking. Large bedrooms, great back patio ,quiet neighborhood. Very comfortable definitely would stay again."
United States
Donald S.
Newly updated/furnished 3 bedrooms house

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Spencer
10.0 out of 10, Exceptional, (200)
"Great time spent with family"
Canada
Marianne B.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
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 Dudley Hotel Reviews

Find out more about Dudley

Everything you need to know about Dudley 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 Dudley 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 Dudley holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Dudley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dudley. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dudley 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 Dudley holiday rentals we have selected for you start as low as AU$255 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Dudley rentals

At Expedia, we put the best Dudley 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 Dudley 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 Dudley 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 Dudley. 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

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 Lakefront Home! Book Your Getaway!: This holiday home rental outside of Dudley is located on a lake, and has a patio, a selection of games 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.

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?

Stevens Park and Berthol Field are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include TriState Speedway. Dudley Hill Golf Club at Nichols College and Conant Library are other places to visit while you're in town.

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.