Dudley Holiday Rentals

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Holiday Rentals in Dudley

Trainmaster's Inn - Caboose
9.6 out of 10, Exceptional, (8)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is AU$514
includes taxes & fees
27 Oct - 28 Oct
Trainmaster's Inn - Caboose
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!"
United States
Becky B.
The price is AU$269
includes taxes & fees
22 Oct - 23 Oct
The Tree House at Underhill Hollow
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
9.8 out of 10, Exceptional, (25)
"This prperty was GREAT! Clean, and very accomadating. Had everything you would need staying there. Didn't get to use the lake but sitting on the deck was relaxing. Will book again. 10 Stars!! Thank You!"
United States
WILLIAM
The price is AU$479
includes taxes & fees
22 Oct - 23 Oct
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Wizard's Roost at Underhill Hollow
9.6 out of 10, Exceptional, (19)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
The price is AU$244
includes taxes & fees
22 Oct - 23 Oct
Wizard's Roost at Underhill Hollow
Dove Cabin up in the Trees
9.8 out of 10, Exceptional, (27)
"A sweet, cozy, nostalgic little cabin in the woods. It was the perfect stop over on our road trip to Acadia. Very peaceful, and the screened in porch was wonderful to relax on before bed and during breakfast. "
United States
Maggie G.
The price is AU$403
includes taxes & fees
22 Oct - 23 Oct
Dove Cabin up in the Trees
Treehouse - Countryside - Farm Animals - Fire Pit
9.4 out of 10, Exceptional, (27)
"Safe, inviting stay."
United States
Gabe M.
The price is AU$433
includes taxes & fees
27 Oct - 28 Oct
Treehouse - Countryside - Farm Animals - Fire Pit
SteamPunk Bunk House and Intergalactic Way Station
10.0 out of 10, Exceptional, (12)
"We had a great time staying here. The house was "
United States
Adam B.
The price is AU$260
includes taxes & fees
26 Oct - 27 Oct
SteamPunk Bunk House and Intergalactic Way Station
The Carriage House at Chaprae Hall
10.0 out of 10, Exceptional, (30)
"My husband and I enjoyed our stay for a wedding close by. The Carriage House was clean, artsy and had all the amenities needed for our short trip. We would highly recommend Chaprae Hall."
United States
Christine T.
The price is AU$307
includes taxes & fees
20 Nov - 21 Nov
The Carriage House at Chaprae Hall
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
9.8 out of 10, Exceptional, (10)
"Very educational and fun time on the farm"
United States
David S.
The price is AU$399
includes taxes & fees
27 Oct - 28 Oct
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Charming 2-bedroom apartment in welcoming Putnam
10.0 out of 10, Exceptional, (1)
"Very nice place. Quiet neighborhood and close to town. "
United States
michael C.
The price is AU$295
includes taxes & fees
27 Oct - 28 Oct
Charming 2-bedroom apartment in welcoming Putnam
Spacious, unique barn with beautiful views.
10.0 out of 10, Exceptional, (2)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
The price is AU$410
includes taxes & fees
24 Oct - 25 Oct
Spacious, unique barn with beautiful views.
Apartment in town center #1
8.6 out of 10, Excellent, (24)
"Clean place and was well suited for what we needed"
United States
Chris
The price is AU$450
includes taxes & fees
22 Oct - 23 Oct
Apartment in town center #1
Zen Inspired Retreat with Private Forest Trails
10.0 out of 10, Exceptional, (14)
"Very comfortable and relaxing on the inside with beautiful surroundings and hiking trails right on the property. Exactly what we wanted for a get-away and such close proximity to the zoo where we attended a wedding."
United States
Tammie K.
The price is AU$349
includes taxes & fees
17 Nov - 18 Nov
Zen Inspired Retreat with Private Forest Trails
Stunning Lakefront Escape! Book Your Dream Getaway!
10.0 out of 10, Exceptional, (19)
"We had a great stay at the lakehouse. Will definitely consider a future stay."
United States
Savanna
The price is AU$737
includes taxes & fees
2 Nov - 3 Nov
Stunning Lakefront Escape! Book Your Dream Getaway!
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
9.6 out of 10, Exceptional, (17)
"Highly recommend for a peaceful location that offers everything you need to feel at home. "
United States
Gilles R.
The price is AU$623
includes taxes & fees
2 Nov - 3 Nov
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
New renovation cozy house in Worcester
2.0 star property
9.8 out of 10, Exceptional, (14)
"A very lovely stay , calm and quiet "
United States
Alex R.
The price is AU$887
includes taxes & fees
14 Nov - 15 Nov
New renovation cozy house in Worcester
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
9.6 out of 10, Exceptional, (5)
"Owner was easy to communicate with. Cute and cozy unit that meet all of our needs for our trip."
United States
Rachele T.
The price is AU$511
includes taxes & fees
27 Oct - 28 Oct
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Full House/Heart of Worcester
7.4 out of 10, Good, (3)
"The space was very clean"
United States
Jaclyn
The price is AU$783
includes taxes & fees
3 Nov - 4 Nov
Full House/Heart of Worcester
Spacious Massachusetts Apartment #2
9.0 out of 10, Wonderful, (27)
"The apartment was very clean. It’s cozy, but had enough room for my family of 4. The house it’s a classic older New England home. It’s in the downtown part of a small cute town. Overall it was a really good experience!"
United States
Kathleen S.
The price is AU$466
includes taxes & fees
22 Oct - 23 Oct
Spacious Massachusetts Apartment #2
Beautiful two-story home close to downtown worcester 5beds-4bedroom
9.0 out of 10, Wonderful, (17)
"We booked this property to stay with our adult children while visiting family nearby. The house was clean, tastefully decorated, and well maintained. It was an excellent choice for six adults to stay together!"
United States
Susi K.
The price is AU$637
includes taxes & fees
22 Oct - 23 Oct
Beautiful two-story home close to downtown worcester 5beds-4bedroom
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$244 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?

The Tree House at Underhill Hollow: This holiday home rental outside of Dudley offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a coffee maker and kitchenware.

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.