Default HTG hotel image

Dudley Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Dudley holiday rentals

A red building with a colorful mural on the front, a covered porch, and a stone foundation.

1. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
The price is HK$989
HK$1,474 total
includes taxes & fees
5 Oct - 6 Oct
Wizard's Roost at Underhill Hollow
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

2. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is HK$989
HK$1,519 total
includes taxes & fees
5 Oct - 6 Oct
The Tree House at Underhill Hollow
A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

3. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is HK$989
HK$1,474 total
includes taxes & fees
8 Oct - 9 Oct
SteamPunk Bunk House and Intergalactic Way Station
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

4. Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Webster
9.6 out of 10, Exceptional, (5 reviews)
"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 HK$3,923
HK$4,943 total
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
A bedroom with a wooden bed, large windows, and a view of greenery outside.

5. Rustic Farmette Studio with Hot Tub & Pool

Rustic Farmette Studio with Hot Tub & Pool
Thompson
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and quiet location"
United States
Lynn J.
The price is HK$1,726
HK$2,711 total
includes taxes & fees
15 Oct - 16 Oct
Rustic Farmette Studio with Hot Tub & Pool
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

6. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
6.0 out of 10, (3 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is HK$745
HK$1,008 total
includes taxes & fees
5 Oct - 6 Oct
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Bedroom

7. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
The price is HK$691
HK$795 total
includes taxes & fees
5 Oct - 6 Oct
1 King Bed | Non-Smoking, Micfridge
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

8. Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Webster
10.0 out of 10, Exceptional, (3 reviews)
"We loved the space, it accommodated our larger group and had all the amenities we needed. We only stayed 1 night but would have loved to stay longer! The porch area was very nice to sit out on at night."
United States
Kyle C.
The price is HK$5,492
HK$6,915 total
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

9. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is HK$745
HK$1,437 total
includes taxes & fees
18 Oct - 19 Oct
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
A two-story house with a front porch, stone steps, and a driveway.

10. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
9.0 out of 10, Wonderful, (8 reviews)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
The price is HK$953
HK$1,720 total
includes taxes & fees
6 Oct - 7 Oct
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

11. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is HK$1,177
HK$2,471 total
includes taxes & fees
28 Oct - 29 Oct
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

12. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
The price is HK$628
HK$899 total
includes taxes & fees
5 Oct - 6 Oct
Clean & Cozy Private-3 floor_R 2
A wooden cabin with a glass upper floor, surrounded by a forest.

13. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is HK$1,377
HK$2,019 total
includes taxes & fees
6 Oct - 7 Oct
Dove Cabin up in the Trees
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

14. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (19 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
The price is HK$738
HK$1,947 total
includes taxes & fees
18 Oct - 19 Oct
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

15. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (10 reviews)
"What a beautiful set up for a pet friendly family stay - candles lit upon arrival and a child’s room filled with toys ready to be enjoyed."
United States
Gregory C.
The price is HK$1,236
HK$1,556 total
includes taxes & fees
6 Oct - 7 Oct
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A dining area with a high ceiling, skylights, and a view of the outdoors.

16. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (93 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is HK$2,942
HK$5,053 total
includes taxes & fees
1 Nov - 2 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

17. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
The price is HK$1,020
HK$2,560 total
includes taxes & fees
5 Oct - 6 Oct
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A house with a white porch, a black door, and a window with a white frame.

18. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.0 out of 10, Wonderful, (4 reviews)
"Great spot, clean and cozy."
United States
Bud n' Mary's Marina B.
The price is HK$1,922
HK$2,462 total
includes taxes & fees
15 Oct - 16 Oct
Cozy 1-bedroom cottage in serene Pomfret.
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

19. Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
The price is HK$1,255
HK$2,056 total
includes taxes & fees
5 Oct - 6 Oct
Angel Sky Challenge
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

20. Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (24 reviews)
"We really appreciated the kindling and firewood for the outdoor fire pit.The house was clean and nice."
United States
Christian C.
The price is HK$2,432
HK$6,672 total
includes taxes & fees
7 Oct - 8 Oct
Lake House in Sturbridge w/All the Views!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Dudley Hotel Reviews

Comfort Inn Auburn - Worcester

Comfort Inn Auburn - Worcester

8/10 Good
"Good"
Frantz 1-night trip
Posted 6 hours ago
Comfort Inn Auburn - Worcester

Find out more about Dudley

Search for holiday rentals in Dudley on Expedia! You can easily find your home rentals, villas, holiday apartments in Dudley using one of the methods below:

  • View our selection of featured holiday rentals in Dudley
  • Use the map to find apartments and other holiday homes in the Dudley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Dudley while they last

Look no further and take a look at our great range of rental properties in Dudley!

Frequently asked questions

Are there holiday rentals in Dudley?

Yes, there are holiday rentals close to the most popular sights in Dudley, 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?

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8: This holiday home rental outside of Dudley is located in a rural location, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Dudley?

Choose from 3 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 get outside and enjoy nature. 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.