Dudley Holiday Rentals

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Holiday Rentals in Dudley

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
21 Oct - 22 Oct
The Tree House at Underhill Hollow
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
21 Oct - 22 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$400
includes taxes & fees
21 Oct - 22 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$495
includes taxes & fees
23 Oct - 24 Oct
Treehouse - Countryside - Farm Animals - Fire Pit
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."
United States
Deb H.
The price is AU$793
includes taxes & fees
21 Oct - 22 Oct
Spacious 4-bedroom with four and half bathrooms
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$481
includes taxes & fees
21 Oct - 22 Oct
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
10.0 out of 10, Exceptional, (198)
"Water front was a perfectly serene escape. House was cute and had everything we needed for a quiet getaway. Would absolutely stay here again. "
United States
Rich L.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Beautiful Lakefront Home with Private Beach
9.4 out of 10, Exceptional, (178)
"Great location for the family. Grandson enjoyed fishing and family swimming, cookouts and fire pit. "
United States
PeterJanet S.
Beautiful Lakefront Home with Private Beach
Amazing lake house with everything you need!
9.6 out of 10, Exceptional, (20)
"Great time, lovely location, easy to access and beautiful lake!"
United States
Sam L.
Amazing lake house with everything you need!
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$467
includes taxes & fees
21 Oct - 22 Oct
Spacious Massachusetts Apartment #2
One Bedroom Apartment with Separate Bunk Bed Area
9.6 out of 10, Exceptional, (22)
"My family had a wonderful stay! We attended a weekend event at WPI and this was a great location to rest after a long day. Our kids especially enjoyed the large TV in the living room. It was clean and communication/ instructions were clear. Thanks! "
United States
Katie M.
One Bedroom Apartment with Separate Bunk Bed Area
Home Away from Home!
9.4 out of 10, Exceptional, (13)
"The property was nice and accommodating for my family! "
United States
Ykeca M.
The price is AU$604
includes taxes & fees
23 Oct - 24 Oct
Home Away from Home!
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!
10.0 out of 10, Exceptional, (134)
"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."
United States
Anonymous traveller
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
9.6 out of 10, Exceptional, (28)
"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.
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
10.0 out of 10, Exceptional, (6)
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
Brimfield Waterfront cottage
10.0 out of 10, Exceptional, (11)
"The cabin was definitely cozy, the treats were a nice addition, and the kitchen had most of what we needed. Would return next time we plan to be in the area. Gus was great to communicate with! Thank you@"
United States
Debora
Brimfield Waterfront cottage
Newly updated/furnished 3 bedrooms house
8.8 out of 10, Excellent, (12)
"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!"
United States
Isabelle G.
Newly updated/furnished 3 bedrooms house
SalsVista 2nd Floor Corner Apt
10.0 out of 10, Exceptional, (4)
"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
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
9.2 out of 10, Wonderful, (23)
"Hosted a bachelorette trip at this property and it was fantastic. The kayaks and paddle boards provided plenty to do along with a firepit to sit around at night. The house was cozy with plenty of space to sleep 5. Had a great time! "
United States
Renee J.
The price is AU$635
includes taxes & fees
2 Nov - 3 Nov
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
10.0 out of 10, Exceptional, (13)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
United States
JUNE
The price is AU$905
includes taxes & fees
22 Oct - 23 Oct
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
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.